research communications
S,2R)-2-hydroxy-1,2-diphenylethan-1-aminium (S)-2-azaniumylbutanedioate monohydrate
of (1aSchool of Science, Tokai University, 4-1-1 Kitakaname, Hiratuka, Kanagawa 259-1292, Japan
*Correspondence e-mail: fujii@wing.ncc.u-tokai.ac.jp
The title diastereomeric salt, formed between 2-amino-1,2-diphenylethanol (ADE) and aspartic acid (ASP), C14H16NO+·C4H6NO4−·H2O, crystallizes as a monohydrate. The 1,2-diphenylethyl group in the cation has a cis conformation, and the aspartic acid anion is in the zwitterionic form. In the crystal, the ASP anions are linked via N—H⋯O hydrogen bonds to form a 21 helix along the b-axis direction. The helices are linked by the ADE cations via O—H⋯O and N—H⋯O hydrogen bonds, forming layers parallel to the bc plane. There are channels in the layers that are occupied by water molecules, which link to both the anions and cations via Owater—H⋯O and N—H⋯Owater hydrogen bonds. There are also C—H⋯O and C—H⋯π interactions present within the layers.
Keywords: crystal structure; diastereomeric salt separation; zwitterion; intermolecular hydrogen bonding; helical columnar structure.
CCDC reference: 1582706
1. Chemical context
The production of chiral compounds has great importance in the pharmaceutical industry, and diastereomeric salt separation is still widely applied in the process. A synthetic optical resolving agent, chiral 2-amino-1,2-diphenylethanol (ADE) (Read & Steele, 1927), has been widely tried and used in diastereomeric salt-separation methods for chiral or organic acids. L-(S)-aspartic acid (ASP) is a known neurotransmitter, and D-(R)-ASP is a non-essential amino acid, one of two D-amino acids commonly found in mammals. D-ASP has also attracted attention as residue in the antifungal bacitracin, while N-methyl-D-aspartic acid (NMDA) acts as a specific agonist at the NMDA receptor. D-amino acids are mainly resolved enzymatically with D-aminoacylase (EC 3.5.1.14) in industrial applications. The optical separation of ASP with cis-ADE was introduced without chemical modification. The of the title molecular salt, formed between L-(S)-ASP and (1R,2S)-cis-ADE, is reported herein.
2. Structural commentary
The molecular structures of the components of the title salt are shown in Fig. 1, and selected torsion angles are given in Table 1. It can be seen that the hydroxy and protonated amino groups of cis-ADE form a tweezer-like motif. The dihedral angle between the phenyl rings (A and B; Fig.1) is 48.71 (9)° and the torsion angle O1A—C1A—C2A—N1A is −65.0 (2)°. The hydroxy group adopts a gauche conformation [O1A—C1A—C2A—C9A = 60.1 (2)°] with respect to phenyl ring B. Thus, the tweezer-like motif is twisted with respect to the phenyl groups. This arrangement is similar to that found in racemic cis-ADE (Fujii, 2015) and the diastereomeric salts formed with cis-enantiomers.
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L-(S)-ASP crystallizes as a deprotonated zwitterion. The succinate group adopts a cis conformation [C1B—C2B—C3B—C4B = −53.0 (2)°], which is the motif commonly found in L-ASP salts; for example L-His·L-ASP monohydrate (Suresh & Vijayan, 1987). The amino and residual carboxy groups have a slightly right-handed helical-shape; torsion angles N1B—C2B—C3B—C4B and C2B—C3B—C4B—O3B are 73.0 (2) and 1.4 (3)°, respectively.
3. Supramolecular features
In the crystal, the (S)-ASP anions correlated with are linked via N1B—H1B3⋯O4Bii [2.868 (2) Å] hydrogen bonds into C(6) chains to form a right-handed 21-helix along the b-axis direction (Fig. 2 and Table 2). The helices are linked by the (1R,2S)-cis-ADE cations via N—H⋯O hydrogen bonds [N1A—H1A2⋯O1B = 2.862 (2) Å and N1A—H1A1⋯O4Biii = 2.742 (3) Å] and O—H⋯O hydrogen bonds [O1A—H1O1⋯O2Bi = 2.752 (2) Å], forming layers parallel to the bc plane (Fig. 3, Table 2). There are channels in the layers that are occupied by water molecules which link to both the anions and cations via tetrahedrally placed hydrogen bonds; Owater—H⋯O hydrogen bonds [O1C—H1OB⋯O1Bi = 2.734 (2) Å and O1C—H1OA⋯O1Biv = 2.840 (2) Å] and N—H⋯Owater hydrogen bonds [N1B—H1B2⋯O1C = 2.938 (2) Å and N1A—H1A3⋯O1C = 2.926 (3) Å], shown in Fig. 4; see also Table 2. There are also C—H⋯O and C—H⋯π interactions present within the layers (Table 2). Finally, the hydrophobic and hydrophilic layers are well separated along the a-axis direction.
4. Database survey
The author has reported the crystal structures of several amino acids without chemical modification including the chiral resolving agents; 1,1′-binaphthalene-2,2′-diyl hydrogen phosphate, 2-phenoxypropionic acid and mandelic acid (Fujii & Hirayama, 2002; Fujii et al., 2005, 2006). The crystal structures of racemic trans- and cis-ADE have been reported (GAQXON: Bari et al., 2012; RUTROP: Fujii, 2015, respectively). Recently, the solvent-induced switching in between mandelic acid and cis-ADE has been demonstrated (Shitara et al., 2013). Moreover, a database search (CSD Version 5.28, last update May 2017; Groom et al., 2016) yielded other comparable structures, viz. L-aspartic acid (LASPRT: Derissen et al., 1968), L-aspartic acid monohydrate (IJEQET: Umadevi et al., 2003) and N-methyl-D-aspartic acid monohydrate (KEWGUO: Sawka-Dobrowolska et al., 1990).
5. Synthesis and crystallization
(1R,2S)-cis-2-Amino-1,2-diphenylethanol (ADE) and aspartic acid (ASP) were purchased from Sigma–Aldrich Co. Ltd. The title molecular salt was obtained from an aqueous ethanol solution of racemic-ASP and (1R,2S)-cis-ADE in a 2:1 molar ratio, heated to 333 K under stirring. On slow cooling to ambient temperature and slow evaporation of the solvent, colourless rod-shaped crystals were obtained.
6. Refinement
Crystal data, data collection and structure . All the H atoms were located in difference-Fourier maps. The NH3+, OH, and water H atoms were freely refined. The C-bound H atoms were included in calculated positions and treated as riding atoms: C—H = 0.93–0.98 Å with Uiso(H) = 1.2Ueq(C).
details are summarized in Table 3
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Supporting information
CCDC reference: 1582706
https://doi.org/10.1107/S2056989017015729/su5398sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989017015729/su5398Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989017015729/su5398Isup3.cml
Data collection: CAD4 (Enraf–Nonius, 1994); cell
CAD4 (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS86 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2017 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: PLATON (Spek, 2009), WinGX (Farrugia, 2012) and publCIF (Westrip, 2010).C14H16NO+·C4H6NO4−·H2O | F(000) = 388 |
Mr = 364.39 | Dx = 1.36 Mg m−3 |
Monoclinic, P21 | Cu Kα radiation, λ = 1.54178 Å |
Hall symbol: P 2yb | Cell parameters from 25 reflections |
a = 18.310 (8) Å | θ = 28.2–34.6° |
b = 5.2661 (10) Å | µ = 0.86 mm−1 |
c = 9.2792 (10) Å | T = 297 K |
β = 96.070 (4)° | Rod, colorless |
V = 889.7 (4) Å3 | 0.4 × 0.2 × 0.2 mm |
Z = 2 |
Enraf–Nonius CAD-4 diffractometer | 1907 reflections with I > 2σ(I) |
Radiation source: Enraf Nonius FR590 | Rint = 0.020 |
Graphite monochromator | θmax = 74.9°, θmin = 2.4° |
non–profiled ω/2τ scans | h = 0→22 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→6 |
Tmin = 0.74, Tmax = 0.86 | l = −11→11 |
2114 measured reflections | 3 standard reflections every 60 min |
2051 independent reflections | intensity decay: 5% |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.028 | w = 1/[σ2(Fo2) + (0.0517P)2 + 0.0743P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.079 | (Δ/σ)max < 0.001 |
S = 1.06 | Δρmax = 0.17 e Å−3 |
2051 reflections | Δρmin = −0.13 e Å−3 |
272 parameters | Extinction correction: (SHELXL2017; Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
1 restraint | Extinction coefficient: 0.0104 (12) |
0 constraints | Absolute structure: No quotients, so Flack (1983) parameter determined by classical intensity fit |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.1 (2) |
Secondary atom site location: difference Fourier map |
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 | ||
C1B | 0.86265 (9) | 0.1336 (4) | 0.25943 (17) | 0.0285 (3) | |
C2B | 0.87228 (9) | 0.3556 (4) | 0.15574 (17) | 0.0281 (3) | |
H2B | 0.834662 | 0.481729 | 0.171984 | 0.034* | |
C3B | 0.86125 (10) | 0.2862 (4) | −0.00305 (18) | 0.0331 (4) | |
H3B1 | 0.872821 | 0.433561 | −0.059083 | 0.040* | |
H3B2 | 0.809703 | 0.247484 | −0.028525 | 0.040* | |
C4B | 0.90650 (9) | 0.0630 (4) | −0.04800 (18) | 0.0309 (4) | |
N1B | 0.94481 (9) | 0.4807 (4) | 0.19193 (17) | 0.0344 (3) | |
O1B | 0.90523 (7) | 0.1301 (3) | 0.37604 (13) | 0.0363 (3) | |
O2B | 0.81052 (7) | −0.0126 (3) | 0.22709 (14) | 0.0410 (3) | |
O3B | 0.94788 (7) | −0.0504 (3) | 0.04607 (14) | 0.0378 (3) | |
O4B | 0.89947 (7) | 0.0126 (3) | −0.18182 (14) | 0.0437 (4) | |
H1B1 | 0.9480 (15) | 0.620 (7) | 0.134 (3) | 0.064 (8)* | |
H1B2 | 0.9537 (12) | 0.517 (5) | 0.294 (3) | 0.044 (6)* | |
H1B3 | 0.9841 (16) | 0.405 (7) | 0.168 (3) | 0.069 (9)* | |
C1A | 0.73892 (10) | 0.5069 (4) | 0.44043 (19) | 0.0329 (4) | |
H1A | 0.768063 | 0.436672 | 0.367158 | 0.039* | |
C2A | 0.75763 (9) | 0.3549 (4) | 0.58118 (18) | 0.0326 (4) | |
H2A | 0.741273 | 0.179814 | 0.561992 | 0.039* | |
C3A | 0.65856 (10) | 0.4782 (4) | 0.38426 (18) | 0.0343 (4) | |
C4A | 0.63715 (12) | 0.2766 (5) | 0.2934 (2) | 0.0458 (5) | |
H4A | 0.672227 | 0.164185 | 0.265603 | 0.055* | |
C5A | 0.56362 (13) | 0.2416 (5) | 0.2438 (3) | 0.0547 (6) | |
H5A | 0.549539 | 0.104493 | 0.184080 | 0.066* | |
C6A | 0.51174 (12) | 0.4086 (5) | 0.2827 (3) | 0.0562 (6) | |
H6A | 0.462589 | 0.385662 | 0.248470 | 0.067* | |
C7A | 0.53231 (12) | 0.6099 (6) | 0.3721 (3) | 0.0578 (6) | |
H7A | 0.497042 | 0.722986 | 0.398421 | 0.069* | |
C8A | 0.60593 (11) | 0.6449 (5) | 0.4233 (2) | 0.0450 (5) | |
H8A | 0.619641 | 0.781071 | 0.484053 | 0.054* | |
C9A | 0.72103 (9) | 0.4489 (4) | 0.70990 (17) | 0.0300 (4) | |
C10A | 0.66288 (10) | 0.3106 (4) | 0.7532 (2) | 0.0403 (4) | |
H10A | 0.646344 | 0.166838 | 0.701394 | 0.048* | |
C11A | 0.62902 (13) | 0.3850 (6) | 0.8737 (2) | 0.0551 (6) | |
H11A | 0.589386 | 0.292688 | 0.900760 | 0.066* | |
C12A | 0.65359 (13) | 0.5929 (6) | 0.9524 (2) | 0.0541 (6) | |
H12A | 0.631510 | 0.639855 | 1.034136 | 0.065* | |
C13A | 0.71124 (14) | 0.7326 (5) | 0.9101 (2) | 0.0503 (5) | |
H13A | 0.728153 | 0.873940 | 0.963729 | 0.060* | |
C14A | 0.74423 (11) | 0.6637 (4) | 0.7880 (2) | 0.0397 (4) | |
H14A | 0.782096 | 0.762143 | 0.758481 | 0.048* | |
N1A | 0.83958 (9) | 0.3495 (5) | 0.6135 (2) | 0.0445 (4) | |
O1A | 0.76176 (8) | 0.7615 (3) | 0.46671 (15) | 0.0392 (3) | |
H1A1 | 0.8579 (18) | 0.240 (8) | 0.709 (3) | 0.087 (11)* | |
H1A2 | 0.8600 (15) | 0.288 (7) | 0.530 (3) | 0.067 (9)* | |
H1A3 | 0.8561 (15) | 0.501 (7) | 0.638 (3) | 0.053 (8)* | |
H1O1 | 0.7784 (15) | 0.818 (7) | 0.387 (3) | 0.062 (8)* | |
O1C | 0.94824 (9) | 0.6688 (3) | 0.49070 (19) | 0.0476 (4) | |
H1OB | 0.9297 (17) | 0.820 (9) | 0.453 (3) | 0.077 (10)* | |
H1OA | 0.991 (2) | 0.707 (9) | 0.543 (4) | 0.090 (11)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1B | 0.0317 (7) | 0.0269 (8) | 0.0277 (7) | −0.0005 (7) | 0.0073 (6) | 0.0007 (7) |
C2B | 0.0292 (7) | 0.0260 (8) | 0.0297 (7) | 0.0032 (7) | 0.0054 (6) | 0.0030 (7) |
C3B | 0.0374 (8) | 0.0338 (10) | 0.0280 (7) | 0.0067 (8) | 0.0025 (6) | 0.0061 (7) |
C4B | 0.0312 (7) | 0.0305 (9) | 0.0318 (7) | −0.0023 (7) | 0.0075 (6) | 0.0018 (7) |
N1B | 0.0367 (8) | 0.0300 (8) | 0.0367 (8) | −0.0035 (7) | 0.0050 (6) | 0.0064 (7) |
O1B | 0.0440 (7) | 0.0328 (7) | 0.0312 (6) | −0.0031 (6) | −0.0005 (5) | 0.0062 (6) |
O2B | 0.0437 (7) | 0.0411 (8) | 0.0387 (6) | −0.0143 (7) | 0.0061 (5) | 0.0035 (6) |
O3B | 0.0425 (7) | 0.0308 (7) | 0.0406 (7) | 0.0073 (6) | 0.0068 (5) | 0.0072 (6) |
O4B | 0.0458 (7) | 0.0528 (10) | 0.0328 (6) | 0.0030 (7) | 0.0054 (5) | −0.0066 (6) |
C1A | 0.0359 (9) | 0.0326 (10) | 0.0310 (8) | 0.0018 (8) | 0.0077 (6) | 0.0030 (8) |
C2A | 0.0317 (8) | 0.0334 (9) | 0.0330 (8) | 0.0023 (8) | 0.0041 (6) | 0.0039 (8) |
C3A | 0.0389 (9) | 0.0338 (9) | 0.0300 (7) | 0.0022 (8) | 0.0028 (6) | 0.0045 (8) |
C4A | 0.0485 (11) | 0.0399 (12) | 0.0479 (11) | 0.0043 (10) | 0.0003 (8) | −0.0053 (10) |
C5A | 0.0568 (12) | 0.0483 (13) | 0.0561 (12) | −0.0057 (12) | −0.0075 (10) | −0.0066 (11) |
C6A | 0.0409 (11) | 0.0594 (17) | 0.0655 (14) | −0.0038 (11) | −0.0074 (10) | 0.0067 (12) |
C7A | 0.0395 (10) | 0.0593 (15) | 0.0733 (15) | 0.0108 (12) | −0.0004 (10) | −0.0058 (13) |
C8A | 0.0412 (10) | 0.0426 (11) | 0.0506 (11) | 0.0057 (10) | 0.0015 (8) | −0.0067 (10) |
C9A | 0.0299 (8) | 0.0297 (9) | 0.0298 (8) | 0.0018 (7) | 0.0013 (6) | 0.0039 (7) |
C10A | 0.0378 (9) | 0.0414 (11) | 0.0427 (10) | −0.0083 (9) | 0.0083 (7) | −0.0013 (9) |
C11A | 0.0513 (12) | 0.0670 (17) | 0.0506 (12) | −0.0069 (12) | 0.0213 (9) | 0.0014 (12) |
C12A | 0.0658 (13) | 0.0590 (16) | 0.0399 (10) | 0.0156 (13) | 0.0171 (9) | −0.0001 (11) |
C13A | 0.0746 (14) | 0.0369 (11) | 0.0380 (10) | 0.0047 (11) | −0.0003 (9) | −0.0051 (9) |
C14A | 0.0471 (10) | 0.0332 (10) | 0.0382 (9) | −0.0060 (9) | 0.0016 (7) | 0.0010 (9) |
N1A | 0.0338 (8) | 0.0613 (13) | 0.0392 (9) | 0.0097 (9) | 0.0076 (6) | 0.0119 (9) |
O1A | 0.0455 (7) | 0.0349 (7) | 0.0378 (7) | −0.0054 (6) | 0.0065 (5) | 0.0053 (6) |
O1C | 0.0472 (8) | 0.0297 (8) | 0.0625 (9) | −0.0008 (6) | −0.0098 (7) | −0.0011 (7) |
C1B—O2B | 1.239 (2) | C5A—C6A | 1.370 (4) |
C1B—O1B | 1.265 (2) | C5A—H5A | 0.9300 |
C1B—C2B | 1.536 (2) | C6A—C7A | 1.374 (4) |
C2B—N1B | 1.488 (2) | C6A—H6A | 0.9300 |
C2B—C3B | 1.511 (2) | C7A—C8A | 1.393 (3) |
C2B—H2B | 0.9800 | C7A—H7A | 0.9300 |
C3B—C4B | 1.522 (3) | C8A—H8A | 0.9300 |
C3B—H3B1 | 0.9700 | C9A—C10A | 1.384 (3) |
C3B—H3B2 | 0.9700 | C9A—C14A | 1.386 (3) |
C4B—O3B | 1.246 (2) | C10A—C11A | 1.391 (3) |
C4B—O4B | 1.263 (2) | C10A—H10A | 0.9300 |
N1B—H1B1 | 0.92 (4) | C11A—C12A | 1.365 (4) |
N1B—H1B2 | 0.96 (2) | C11A—H11A | 0.9300 |
N1B—H1B3 | 0.87 (3) | C12A—C13A | 1.377 (4) |
C1A—O1A | 1.418 (2) | C12A—H12A | 0.9300 |
C1A—C3A | 1.516 (3) | C13A—C14A | 1.387 (3) |
C1A—C2A | 1.539 (2) | C13A—H13A | 0.9300 |
C1A—H1A | 0.9800 | C14A—H14A | 0.9300 |
C2A—N1A | 1.499 (2) | N1A—H1A1 | 1.08 (4) |
C2A—C9A | 1.513 (2) | N1A—H1A2 | 0.95 (3) |
C2A—H2A | 0.9800 | N1A—H1A3 | 0.87 (4) |
C3A—C8A | 1.380 (3) | O1A—H1O1 | 0.88 (3) |
C3A—C4A | 1.386 (3) | O1C—H1OB | 0.92 (4) |
C4A—C5A | 1.388 (3) | O1C—H1OA | 0.90 (4) |
C4A—H4A | 0.9300 | ||
O2B—C1B—O1B | 125.99 (17) | C3A—C4A—H4A | 119.8 |
O2B—C1B—C2B | 117.27 (14) | C5A—C4A—H4A | 119.8 |
O1B—C1B—C2B | 116.47 (15) | C6A—C5A—C4A | 120.2 (2) |
N1B—C2B—C3B | 110.56 (14) | C6A—C5A—H5A | 119.9 |
N1B—C2B—C1B | 110.74 (13) | C4A—C5A—H5A | 119.9 |
C3B—C2B—C1B | 114.48 (15) | C5A—C6A—C7A | 120.0 (2) |
N1B—C2B—H2B | 106.9 | C5A—C6A—H6A | 120.0 |
C3B—C2B—H2B | 106.9 | C7A—C6A—H6A | 120.0 |
C1B—C2B—H2B | 106.9 | C6A—C7A—C8A | 120.1 (2) |
C2B—C3B—C4B | 115.70 (14) | C6A—C7A—H7A | 119.9 |
C2B—C3B—H3B1 | 108.4 | C8A—C7A—H7A | 119.9 |
C4B—C3B—H3B1 | 108.4 | C3A—C8A—C7A | 120.2 (2) |
C2B—C3B—H3B2 | 108.4 | C3A—C8A—H8A | 119.9 |
C4B—C3B—H3B2 | 108.4 | C7A—C8A—H8A | 119.9 |
H3B1—C3B—H3B2 | 107.4 | C10A—C9A—C14A | 118.70 (17) |
O3B—C4B—O4B | 125.39 (18) | C10A—C9A—C2A | 118.39 (18) |
O3B—C4B—C3B | 119.12 (15) | C14A—C9A—C2A | 122.89 (16) |
O4B—C4B—C3B | 115.47 (16) | C9A—C10A—C11A | 120.5 (2) |
C2B—N1B—H1B1 | 109.3 (17) | C9A—C10A—H10A | 119.8 |
C2B—N1B—H1B2 | 111.4 (14) | C11A—C10A—H10A | 119.8 |
H1B1—N1B—H1B2 | 114 (3) | C12A—C11A—C10A | 120.4 (2) |
C2B—N1B—H1B3 | 119 (2) | C12A—C11A—H11A | 119.8 |
H1B1—N1B—H1B3 | 96 (3) | C10A—C11A—H11A | 119.8 |
H1B2—N1B—H1B3 | 107 (2) | C11A—C12A—C13A | 119.7 (2) |
O1A—C1A—C3A | 114.28 (16) | C11A—C12A—H12A | 120.2 |
O1A—C1A—C2A | 108.10 (15) | C13A—C12A—H12A | 120.2 |
C3A—C1A—C2A | 111.15 (14) | C12A—C13A—C14A | 120.4 (2) |
O1A—C1A—H1A | 107.7 | C12A—C13A—H13A | 119.8 |
C3A—C1A—H1A | 107.7 | C14A—C13A—H13A | 119.8 |
C2A—C1A—H1A | 107.7 | C9A—C14A—C13A | 120.3 (2) |
N1A—C2A—C9A | 111.47 (15) | C9A—C14A—H14A | 119.8 |
N1A—C2A—C1A | 107.92 (15) | C13A—C14A—H14A | 119.8 |
C9A—C2A—C1A | 114.98 (16) | C2A—N1A—H1A1 | 113.1 (18) |
N1A—C2A—H2A | 107.4 | C2A—N1A—H1A2 | 108.5 (16) |
C9A—C2A—H2A | 107.4 | H1A1—N1A—H1A2 | 111 (3) |
C1A—C2A—H2A | 107.4 | C2A—N1A—H1A3 | 110.3 (18) |
C8A—C3A—C4A | 119.11 (18) | H1A1—N1A—H1A3 | 102 (3) |
C8A—C3A—C1A | 121.73 (18) | H1A2—N1A—H1A3 | 112 (3) |
C4A—C3A—C1A | 119.16 (18) | C1A—O1A—H1O1 | 107 (2) |
C3A—C4A—C5A | 120.4 (2) | H1OB—O1C—H1OA | 106 (4) |
O1A—C1A—C2A—N1A | −65.0 (2) | C5A—C6A—C7A—C8A | 0.1 (4) |
O1A—C1A—C2A—C9A | 60.14 (19) | C6A—C7A—C8A—C3A | 0.2 (4) |
C3A—C1A—C2A—N1A | 168.86 (17) | C2A—C9A—C10A—C11A | 177.95 (19) |
C3A—C1A—C2A—C9A | −66.1 (2) | C14A—C9A—C10A—C11A | −0.6 (3) |
O1A—C1A—C3A—C4A | 149.76 (18) | C2A—C9A—C14A—C13A | −176.29 (19) |
O1A—C1A—C3A—C8A | −31.4 (2) | C10A—C9A—C14A—C13A | 2.2 (3) |
C2A—C1A—C3A—C4A | −87.6 (2) | C9A—C10A—C11A—C12A | −1.2 (3) |
C2A—C1A—C3A—C8A | 91.3 (2) | C10A—C11A—C12A—C13A | 1.4 (4) |
N1A—C2A—C9A—C10A | −131.49 (19) | C11A—C12A—C13A—C14A | 0.2 (4) |
N1A—C2A—C9A—C14A | 47.0 (3) | C12A—C13A—C14A—C9A | −2.0 (3) |
C1A—C2A—C9A—C10A | 105.3 (2) | O1B—C1B—C2B—N1B | 17.4 (2) |
C1A—C2A—C9A—C14A | −76.2 (2) | O1B—C1B—C2B—C3B | 143.24 (16) |
C1A—C3A—C4A—C5A | 178.1 (2) | O2B—C1B—C2B—N1B | −168.28 (16) |
C8A—C3A—C4A—C5A | −0.7 (3) | O2B—C1B—C2B—C3B | −42.5 (2) |
C1A—C3A—C8A—C7A | −178.7 (2) | N1B—C2B—C3B—C4B | 73.0 (2) |
C4A—C3A—C8A—C7A | 0.2 (3) | C1B—C2B—C3B—C4B | −53.0 (2) |
C3A—C4A—C5A—C6A | 1.0 (4) | C2B—C3B—C4B—O3B | 1.4 (3) |
C4A—C5A—C6A—C7A | −0.6 (4) | C2B—C3B—C4B—O4B | −177.08 (16) |
CgB is the centroid of phenyl ring B (C9–C14). |
D—H···A | D—H | H···A | D···A | D—H···A |
N1B—H1B1···O3Bi | 0.92 (4) | 1.92 (4) | 2.819 (2) | 168 (3) |
N1B—H1B3···O3Bii | 0.87 (3) | 2.46 (3) | 3.112 (2) | 132 (3) |
N1B—H1B3···O4Bii | 0.87 (3) | 2.20 (3) | 2.868 (2) | 134 (3) |
O1A—H1O1···O2Bi | 0.88 (3) | 1.88 (3) | 2.752 (2) | 171 (3) |
N1A—H1A1···O4Biii | 1.08 (4) | 1.70 (4) | 2.742 (3) | 162 (3) |
N1A—H1A2···O1B | 0.95 (3) | 1.92 (3) | 2.862 (2) | 173 (3) |
O1C—H1OB···O1Bi | 0.92 (4) | 1.82 (4) | 2.734 (2) | 173 (3) |
O1C—H1OA···O1Biv | 0.90 (4) | 2.01 (4) | 2.840 (2) | 153 (4) |
N1A—H1A3···O1C | 0.87 (4) | 2.45 (3) | 2.926 (3) | 115 (2) |
N1B—H1B2···O1C | 0.96 (2) | 2.01 (3) | 2.938 (2) | 163 (2) |
C2A—H2A···O1Av | 0.98 | 2.42 | 3.304 (3) | 150 |
C14A—H14A···O4Bvi | 0.93 | 2.53 | 3.371 (3) | 150 |
C3B—H3B2···CgBiii | 0.97 | 2.87 | 3.6127 (16) | 134 |
Symmetry codes: (i) x, y+1, z; (ii) −x+2, y+1/2, −z; (iii) x, y, z+1; (iv) −x+2, y+1/2, −z+1; (v) x, y−1, z; (vi) x, y+1, z+1. |
Acknowledgements
The author thanks Tokai University for a research grant, which partially supported this work.
References
Bari, A., Al-Obaid, A. M. & Ng, S. W. (2012). Acta Cryst. E68, o491. Web of Science CSD CrossRef IUCr Journals
Derissen, J. L., Endeman, H. J. & Peerdeman, A. F. (1968). Acta Cryst. B24, 1349–1354. CSD CrossRef CAS IUCr Journals Web of Science
Enraf–Nonius (1994). CAD4. Enraf-Nonius, Delft, The Netherlands.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals
Fujii, I. (2015). Acta Cryst. E71, 1539–1541. CSD CrossRef IUCr Journals
Fujii, I., Baba, H. & Takahashi, Y. (2005). Anal. Sci. X-ray Struct. Anal. Online, 21, x175–176. CSD CrossRef CAS
Fujii, I. & Hirayama, N. (2002). Helv. Chim. Acta, 85, 2946–2960. Web of Science CSD CrossRef CAS
Fujii, I., Watadani, T., Nunomura, S. & Takahashi, Y. (2006). Anal. Sci. X-ray Struct. Anal. Online, 22, x75–x76. CSD CrossRef CAS
Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179. Web of Science CSD CrossRef IUCr Journals
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CSD CrossRef CAS IUCr Journals
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science
Read, J. & Steele, C. C. (1927). J. Chem. Soc. pp. 910–918. CrossRef
Sawka-Dobrowolska, W., Głowiak, T., Kozłowski, H. & Masterlerz, P. (1990). Acta Cryst. C46, 1679–1681. CSD CrossRef CAS Web of Science IUCr Journals
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals
Shitara, H., Shintani, T., Kodama, K. & Hirose, T. (2013). J. Org. Chem. 78, 9309–9316. Web of Science CSD CrossRef CAS PubMed
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals
Suresh, C. G. & Vijayan, M. (1987). J. Biosci. 12, 13–21. CrossRef CAS Web of Science
Umadevi, K., Anitha, K., Sridhar, B., Srinivasan, N. & Rajaram, R. K. (2003). Acta Cryst. E59, o1073–o1075. Web of Science CSD CrossRef IUCr Journals
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals
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