research communications
H-imidazol-1-yl]propan-2-ol
of 1-[2-(4-nitrophenyl)-4,5-diphenyl-1aDepartment of Chemistry, University of Otago, PO Box 56, Dunedin, New Zealand, bFaculty of Science and Engineering, Health Care Division, Manchester Metropolitan University, Manchester M1 5GD, England, cChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, dPharmaceutical Chemistry Department, Faculty of Pharmacy, Al Azhar University, 71515 Assiut, Egypt, eChemistry Department, Faculty of Science, Sohag University, Sohag, Egypt, and fKirkuk University, College of Education, Department of Chemistry, Kirkuk, Iraq
*Correspondence e-mail: shaabankamel@yahoo.com
The title compound, C24H21N3O3, crystallizes with two unique but closely r.m.s. overlay fit = 0.215 Å) comparable molecules (1 and 2) in the of the triclinic In molecule 1, the dihedral angles between the central imidazlole ring and the benzene-ring substituents are 42.51 (9), 45.41 (9) and 56.92 (8)°, respectively. Comparable data for molecule 2 are 39.36 (10), 34.45 (11) and 60.34 (8)°, respectively. The rings at the 2-positions carry p-nitro substituents that subtend dihedral angles of 12.9 (4)° in molecule 1 and 11.7 (4)° in molecule 2 to their respective benzene ring planes. The imidazole rings also have propan-2-ol substituents on the 1-N atoms, which adopt extended conformations for the N—C—C—C chains. In the crystal, classical O—H⋯N hydrogen bonds combine with C—H⋯O, C—H⋯N and C—H⋯π(ring) hydrogen bonds and stack the molecules along the a-axis direction.
CCDC reference: 1565059
1. Chemical context
Imidazole compounds form the core of the structures of some well-known components of human organisms including the amino acid histidine, vitamin-B12, a component of the DNA base structure and the purines, histamine and biotin. It is also present in the structure of many natural or synthetic drug molecules, for example cimetidine, azomycin and metronidazole (Kleeman et al., 1999). Imidazole derivatives display an extensive range of biological activities and are thus used as antibacterial (Vijesh et al., 2011; Lu, et al., 2012), anticancer (Yang et al., 2012; Alkahtani et al., 2012), anti-tubercular (Lu, et al., 2012; Lee et al., 2011), analgesic (Kankala et al., 2013; Gaba et al., 2010) and anti-HIV agents (Zhan et al., 2009). As part of an ongoing study of the synthesis of imidazole-based amino aliphatic e.g. amino ethanol and amino isopropanol (Akkurt et al., 2015; Mohamed et al., 2013a,b; Jasinski et al., 2015), we report here the synthesis and of the title compound.
2. Structural commentary
The title compound, (I), crystallizes with two unique molecules, 1 and 2, in the In the numbering scheme these molecules are differentiated by leading 1 and 2 digits, respectively, Fig. 1.
The unique molecules form dimers in the R22(18) rings, Fig. 1. The two molecules are closely similar and an overlay, Fig. 2 (Macrae et al., 2008), shows an r.m.s. deviation of 0.215 Å with relatively minor variations of the inclinations of the various substituents to the central imidazole rings.
through O212—H210⋯N13 and C253—H253⋯O13 hydrogen bonds that encloseThe structure consists of a basic lophine, 2,4,5-triphenyl-1H-imidazole, skeleton (Yanover & Kaftory, 2009), with isopropanol substituents on the N11 and N21 atoms of the central imidazole rings. The N–C3chains of these substituents are planar, with an N1—C11—C12—C13 torsion angle of 173.09 (19)° in molecule 1 and 171.0 (2)° in molecule 2; these planes are inclined to the imidazole ring planes by 74.96 (12) and 74.78 (12)°. respectively. The benzene rings are inclined to the imidazole ring plane at angles of 42.51 (9) and 39.36 (10)° for C121–C126 and C221–C226, 45.41 (9) and 34.45 (11)° for C141–C146 and C241–C246 and 56.92 (8) and 60.34 (8) for C151–C156 and C251–C256, values that further attest to the close similarities between the structures of the two unique molecules. Bond lengths and angles in the two molecules are also similar and compare well with those found in comparable molecules with isopropanol substituents at the 1-position (Jasinski et al., 2015; Mohamed et al., 2017; Akkurt et al., 2015).
3. Supramolecular features
In the crystal, classical O112—H11O⋯N23 and O212—H21O⋯N13 hydrogen bonds, Table 1, bolstered by weaker C155—H155⋯O22, C242—H242⋯O112 and C253—H253⋯O13 hydrogen bonds link type 1 and type 2 molecules alternately in a head-to-tail fashion into C(8) chains along the b-axis direction, Fig. 3. Chains of alternate molecules also form along c, in this case head-to-head, due to C153—H153⋯Cg5 and C255—H255⋯Cg1 contacts (Cg1 and Cg5 are the centroids of the N11/C12/N13/C14/C15 and N21/C22/N23/C24/C25 rings, respectively) combined with C152—H152⋯O212, C153—H153⋯N21 and C256—H256⋯O112 hydrogen bonds, Fig. 4. Chains exclusively of type 2 molecules form along the third axial direction via C243—H243⋯O23 hydrogen bonds, forming C(13) chains along a, Fig. 5. C145—H145⋯O22 hydrogen bonds link type 1 molecules to these chains, stacking the molecules along a. Overall, these numerous contacts generate layers of molecules of (I) stacked along the a-axis direction, Fig. 6.
4. Database survey
The Cambridge Structural Database (Version 5.38 with three updates; Groom et al., 2016) shows that molecules with the lophine skeleton and a CH2 substituent on N1 are reasonably common with 43 entries. However, restricting the search to compounds with isopropanol substituents on N1 reduces the hits to three reports of our work to produce compounds with 4-benzoic acid (Jasinski et al., 2015) and 4-chloro- (Mohamed et al., 2017) and 2,5-dichloro-substituents (Akkurt et al., 2015) at the 2-position of the imidazole ring. A more recent paper, detailing the use of ionic liquids as catalysts for the preparations of similar compounds, also reports analogues with an unsubstituted phenyl ring and a 2,5-dimethoxy substituted benzene ring at the 2-positions (Marzouk et al. 2017). Other closely related derivatives have ethanol (Mohamed et al., 2013a) and n-propanol substituents on the N1 atom (Mohamed et al., 2015).
5. Synthesis and crystallization
The title compound was prepared according to our previously reported method (Marzouk et al., 2017). Crystals suitable for X-ray analysis were obtained by the slow evaporation method using ethanol as a solvent. M.p. 451–453 K, yield, 87%.
6. Refinement
Crystal data, data collection and structure . The hydrogen atoms of the OH groups on O112 and O212 were located in a difference-Fourier map and their coordinates refined with Uiso = 1.5Ueq (O). All other atoms were refined using a riding model with d(C—H) = 0.95 Å for aromatic, 1.00 Å for methine and 0.98 Å for CH2 atoms, all with Uiso(H) = 1.2Ueq(C). For methyl H atoms d(C—H) = 0.98 Å and Uiso(H) = 1.5Ueq(C). One low angle reflection with Fo << Fc that may have been affected by the beamstop was omitted from the final cycles.
details are summarized in Table 2
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Supporting information
CCDC reference: 1565059
https://doi.org/10.1107/S2056989017011057/hg5491sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989017011057/hg5491Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989017011057/hg5491Isup3.cml
Data collection: CrysAlis PRO (Agilent, 2014); cell
CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b) and TITAN (Hunter & Simpson, 1999); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015b), enCIFer (Allen et al., 2004), PLATON (Spek, 2009), publCIF (Westrip, 2010) and WinGX (Farrugia, 2012).C24H21N3O3 | Z = 4 |
Mr = 399.44 | F(000) = 840 |
Triclinic, P1 | Dx = 1.273 Mg m−3 |
a = 12.3070 (4) Å | Cu Kα radiation, λ = 1.54184 Å |
b = 13.2871 (4) Å | Cell parameters from 19318 reflections |
c = 13.8499 (3) Å | θ = 3.3–76.2° |
α = 90.907 (2)° | µ = 0.69 mm−1 |
β = 100.748 (2)° | T = 100 K |
γ = 109.938 (3)° | Block, yellow |
V = 2083.95 (11) Å3 | 0.52 × 0.48 × 0.24 mm |
Agilent SuperNova, Dual, Cu at zero, Atlas diffractometer | 8686 independent reflections |
Radiation source: SuperNova (Cu) X-ray Source | 7364 reflections with I > 2σ(I) |
Detector resolution: 5.1725 pixels mm-1 | Rint = 0.090 |
ω scans | θmax = 76.4°, θmin = 3.3° |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | h = −15→15 |
Tmin = 0.728, Tmax = 1.000 | k = −16→16 |
42589 measured reflections | l = −17→17 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.072 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.216 | w = 1/[σ2(Fo2) + (0.1211P)2 + 1.8979P] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max < 0.001 |
8686 reflections | Δρmax = 0.58 e Å−3 |
549 parameters | Δρmin = −0.39 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. |
Refinement. One low angle reflection with Fo <<< Fc that may have been affected by the beamstop was omitted from the final refinement cycles. |
x | y | z | Uiso*/Ueq | ||
N11 | 0.47399 (16) | 0.32171 (14) | 0.60492 (13) | 0.0183 (4) | |
C111 | 0.39745 (19) | 0.21294 (16) | 0.56313 (16) | 0.0194 (4) | |
H11A | 0.3890 | 0.2091 | 0.4905 | 0.023* | |
H11B | 0.3181 | 0.1981 | 0.5779 | 0.023* | |
C112 | 0.4456 (2) | 0.12685 (17) | 0.60368 (16) | 0.0208 (4) | |
H112 | 0.5289 | 0.1458 | 0.5951 | 0.025* | |
O112 | 0.44400 (15) | 0.12926 (13) | 0.70570 (11) | 0.0224 (3) | |
H11O | 0.451 (3) | 0.071 (3) | 0.731 (2) | 0.034* | |
C113 | 0.3715 (2) | 0.01767 (19) | 0.54911 (19) | 0.0293 (5) | |
H11C | 0.3980 | −0.0378 | 0.5805 | 0.044* | |
H11D | 0.3804 | 0.0183 | 0.4802 | 0.044* | |
H11E | 0.2883 | 0.0022 | 0.5514 | 0.044* | |
C12 | 0.45419 (19) | 0.38744 (16) | 0.67156 (16) | 0.0180 (4) | |
C121 | 0.35006 (19) | 0.36587 (17) | 0.71663 (16) | 0.0199 (4) | |
C122 | 0.2969 (2) | 0.26889 (17) | 0.75549 (17) | 0.0218 (4) | |
H122 | 0.3266 | 0.2120 | 0.7520 | 0.026* | |
C123 | 0.2005 (2) | 0.25551 (18) | 0.79922 (18) | 0.0247 (5) | |
H123 | 0.1650 | 0.1903 | 0.8269 | 0.030* | |
C124 | 0.1573 (2) | 0.33862 (19) | 0.80183 (18) | 0.0259 (5) | |
N124 | 0.0529 (2) | 0.32242 (18) | 0.84456 (19) | 0.0351 (5) | |
O12 | 0.0194 (2) | 0.24368 (19) | 0.89045 (18) | 0.0479 (6) | |
O13 | 0.00229 (19) | 0.38771 (18) | 0.8305 (2) | 0.0506 (6) | |
C125 | 0.2084 (2) | 0.43608 (19) | 0.76456 (19) | 0.0268 (5) | |
H125 | 0.1770 | 0.4920 | 0.7670 | 0.032* | |
C126 | 0.3061 (2) | 0.44945 (18) | 0.72384 (18) | 0.0239 (5) | |
H126 | 0.3442 | 0.5165 | 0.7003 | 0.029* | |
N13 | 0.54166 (16) | 0.48177 (14) | 0.68955 (13) | 0.0191 (4) | |
C14 | 0.62122 (19) | 0.47744 (17) | 0.63342 (16) | 0.0192 (4) | |
C141 | 0.7291 (2) | 0.57016 (17) | 0.63058 (17) | 0.0212 (4) | |
C142 | 0.8016 (2) | 0.62895 (18) | 0.71690 (18) | 0.0259 (5) | |
H142 | 0.7816 | 0.6102 | 0.7788 | 0.031* | |
C143 | 0.9035 (2) | 0.7153 (2) | 0.7129 (2) | 0.0315 (5) | |
H143 | 0.9533 | 0.7547 | 0.7721 | 0.038* | |
C144 | 0.9328 (2) | 0.74408 (19) | 0.6222 (2) | 0.0307 (5) | |
H144 | 1.0024 | 0.8030 | 0.6196 | 0.037* | |
C145 | 0.8599 (2) | 0.6864 (2) | 0.5359 (2) | 0.0297 (5) | |
H145 | 0.8789 | 0.7061 | 0.4738 | 0.036* | |
C146 | 0.7589 (2) | 0.59978 (19) | 0.54048 (18) | 0.0250 (5) | |
H146 | 0.7096 | 0.5601 | 0.4812 | 0.030* | |
C15 | 0.58139 (19) | 0.37866 (17) | 0.58023 (16) | 0.0192 (4) | |
C151 | 0.6379 (2) | 0.33771 (17) | 0.51106 (16) | 0.0200 (4) | |
C152 | 0.5831 (2) | 0.30527 (17) | 0.41259 (16) | 0.0214 (4) | |
H152 | 0.5049 | 0.3041 | 0.3895 | 0.026* | |
C153 | 0.6425 (2) | 0.27454 (18) | 0.34782 (18) | 0.0254 (5) | |
H153 | 0.6040 | 0.2512 | 0.2811 | 0.030* | |
C154 | 0.7571 (2) | 0.2778 (2) | 0.37998 (19) | 0.0291 (5) | |
H154 | 0.7975 | 0.2575 | 0.3354 | 0.035* | |
C155 | 0.8127 (2) | 0.3108 (2) | 0.4775 (2) | 0.0308 (5) | |
H155 | 0.8915 | 0.3134 | 0.4998 | 0.037* | |
C156 | 0.7531 (2) | 0.34025 (19) | 0.54298 (17) | 0.0254 (5) | |
H156 | 0.7915 | 0.3622 | 0.6100 | 0.030* | |
N21 | 0.53514 (16) | 0.84449 (14) | 0.89788 (13) | 0.0178 (4) | |
C211 | 0.6129 (2) | 0.78650 (17) | 0.94029 (16) | 0.0211 (4) | |
H21A | 0.6196 | 0.7890 | 1.0127 | 0.025* | |
H21B | 0.6928 | 0.8231 | 0.9271 | 0.025* | |
C212 | 0.5678 (2) | 0.66925 (18) | 0.89808 (16) | 0.0218 (4) | |
H212 | 0.4833 | 0.6350 | 0.9034 | 0.026* | |
O212 | 0.57451 (15) | 0.67128 (13) | 0.79728 (12) | 0.0247 (4) | |
H21O | 0.559 (3) | 0.606 (3) | 0.769 (3) | 0.037* | |
C213 | 0.6397 (3) | 0.6084 (2) | 0.9554 (2) | 0.0331 (6) | |
H21C | 0.6128 | 0.5346 | 0.9252 | 0.050* | |
H21D | 0.6294 | 0.6073 | 1.0239 | 0.050* | |
H21E | 0.7234 | 0.6442 | 0.9540 | 0.050* | |
C22 | 0.55613 (19) | 0.92431 (16) | 0.83472 (16) | 0.0186 (4) | |
C221 | 0.65812 (19) | 0.96701 (17) | 0.78737 (16) | 0.0193 (4) | |
C222 | 0.6966 (2) | 1.07800 (18) | 0.77616 (17) | 0.0220 (4) | |
H222 | 0.6612 | 1.1216 | 0.8040 | 0.026* | |
C223 | 0.7853 (2) | 1.12438 (19) | 0.72527 (18) | 0.0242 (5) | |
H223 | 0.8119 | 1.1994 | 0.7184 | 0.029* | |
C224 | 0.8346 (2) | 1.05887 (19) | 0.68452 (17) | 0.0236 (5) | |
N224 | 0.92519 (18) | 1.10743 (18) | 0.62720 (16) | 0.0287 (4) | |
O22 | 0.96751 (17) | 1.20609 (16) | 0.63188 (15) | 0.0366 (4) | |
O23 | 0.9549 (2) | 1.04823 (19) | 0.57759 (18) | 0.0479 (6) | |
C225 | 0.7994 (2) | 0.94926 (19) | 0.69411 (17) | 0.0235 (5) | |
H225 | 0.8348 | 0.9063 | 0.6653 | 0.028* | |
C226 | 0.7115 (2) | 0.90354 (18) | 0.74671 (17) | 0.0224 (4) | |
H226 | 0.6874 | 0.8288 | 0.7551 | 0.027* | |
N23 | 0.46808 (16) | 0.96207 (14) | 0.81808 (14) | 0.0192 (4) | |
C24 | 0.38696 (19) | 0.90515 (17) | 0.87159 (16) | 0.0198 (4) | |
C241 | 0.27705 (19) | 0.92635 (17) | 0.87218 (17) | 0.0203 (4) | |
C242 | 0.2189 (2) | 0.95697 (18) | 0.78775 (17) | 0.0225 (4) | |
H242 | 0.2500 | 0.9640 | 0.7294 | 0.027* | |
C243 | 0.1155 (2) | 0.97731 (18) | 0.7888 (2) | 0.0265 (5) | |
H243 | 0.0764 | 0.9980 | 0.7309 | 0.032* | |
C244 | 0.0689 (2) | 0.96790 (19) | 0.8728 (2) | 0.0299 (5) | |
H244 | −0.0018 | 0.9819 | 0.8728 | 0.036* | |
C245 | 0.1262 (2) | 0.9377 (2) | 0.9576 (2) | 0.0298 (5) | |
H245 | 0.0946 | 0.9310 | 1.0157 | 0.036* | |
C246 | 0.2299 (2) | 0.91744 (19) | 0.95732 (18) | 0.0258 (5) | |
H246 | 0.2690 | 0.8974 | 1.0155 | 0.031* | |
C25 | 0.42676 (19) | 0.83105 (17) | 0.92131 (16) | 0.0188 (4) | |
C251 | 0.3663 (2) | 0.74902 (17) | 0.98272 (16) | 0.0197 (4) | |
C252 | 0.2548 (2) | 0.67459 (19) | 0.94172 (18) | 0.0255 (5) | |
H252 | 0.2227 | 0.6737 | 0.8737 | 0.031* | |
C253 | 0.1905 (2) | 0.6023 (2) | 0.9986 (2) | 0.0310 (5) | |
H253 | 0.1147 | 0.5522 | 0.9697 | 0.037* | |
C254 | 0.2371 (2) | 0.6029 (2) | 1.0986 (2) | 0.0306 (5) | |
H254 | 0.1930 | 0.5537 | 1.1381 | 0.037* | |
C255 | 0.3483 (2) | 0.6756 (2) | 1.13974 (18) | 0.0271 (5) | |
H255 | 0.3807 | 0.6755 | 1.2076 | 0.032* | |
C256 | 0.4129 (2) | 0.74873 (18) | 1.08274 (17) | 0.0226 (4) | |
H256 | 0.4888 | 0.7986 | 1.1118 | 0.027* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N11 | 0.0253 (9) | 0.0140 (8) | 0.0201 (9) | 0.0118 (7) | 0.0059 (7) | 0.0034 (7) |
C111 | 0.0244 (10) | 0.0148 (9) | 0.0207 (10) | 0.0093 (8) | 0.0038 (8) | 0.0015 (8) |
C112 | 0.0305 (11) | 0.0165 (10) | 0.0200 (10) | 0.0135 (8) | 0.0061 (8) | 0.0021 (8) |
O112 | 0.0357 (9) | 0.0183 (7) | 0.0199 (8) | 0.0173 (7) | 0.0061 (6) | 0.0033 (6) |
C113 | 0.0416 (13) | 0.0169 (11) | 0.0304 (12) | 0.0128 (10) | 0.0050 (10) | −0.0001 (9) |
C12 | 0.0248 (10) | 0.0135 (9) | 0.0193 (10) | 0.0109 (8) | 0.0052 (8) | 0.0018 (7) |
C121 | 0.0233 (10) | 0.0173 (10) | 0.0218 (10) | 0.0106 (8) | 0.0048 (8) | 0.0005 (8) |
C122 | 0.0272 (11) | 0.0151 (10) | 0.0270 (11) | 0.0113 (8) | 0.0080 (9) | 0.0017 (8) |
C123 | 0.0284 (11) | 0.0194 (10) | 0.0277 (11) | 0.0082 (9) | 0.0091 (9) | 0.0015 (9) |
C124 | 0.0248 (11) | 0.0242 (11) | 0.0312 (12) | 0.0099 (9) | 0.0101 (9) | −0.0026 (9) |
N124 | 0.0310 (11) | 0.0307 (11) | 0.0463 (13) | 0.0090 (9) | 0.0183 (10) | −0.0043 (10) |
O12 | 0.0452 (12) | 0.0458 (12) | 0.0606 (14) | 0.0141 (10) | 0.0324 (11) | 0.0132 (10) |
O13 | 0.0404 (11) | 0.0397 (12) | 0.0850 (18) | 0.0215 (9) | 0.0314 (11) | 0.0010 (11) |
C125 | 0.0303 (12) | 0.0203 (11) | 0.0356 (13) | 0.0145 (9) | 0.0104 (10) | −0.0013 (9) |
C126 | 0.0305 (11) | 0.0164 (10) | 0.0288 (11) | 0.0118 (9) | 0.0088 (9) | 0.0025 (8) |
N13 | 0.0259 (9) | 0.0143 (8) | 0.0212 (9) | 0.0107 (7) | 0.0080 (7) | 0.0025 (7) |
C14 | 0.0257 (10) | 0.0165 (10) | 0.0198 (10) | 0.0123 (8) | 0.0060 (8) | 0.0031 (8) |
C141 | 0.0259 (10) | 0.0155 (10) | 0.0277 (11) | 0.0123 (8) | 0.0087 (9) | 0.0036 (8) |
C142 | 0.0323 (12) | 0.0196 (11) | 0.0281 (12) | 0.0108 (9) | 0.0089 (9) | −0.0009 (9) |
C143 | 0.0321 (12) | 0.0222 (11) | 0.0398 (14) | 0.0090 (10) | 0.0080 (11) | −0.0041 (10) |
C144 | 0.0280 (12) | 0.0204 (11) | 0.0485 (15) | 0.0096 (9) | 0.0172 (11) | 0.0038 (10) |
C145 | 0.0340 (12) | 0.0254 (12) | 0.0382 (13) | 0.0150 (10) | 0.0187 (11) | 0.0098 (10) |
C146 | 0.0308 (11) | 0.0220 (11) | 0.0270 (11) | 0.0129 (9) | 0.0098 (9) | 0.0046 (9) |
C15 | 0.0249 (10) | 0.0163 (10) | 0.0203 (10) | 0.0119 (8) | 0.0051 (8) | 0.0043 (8) |
C151 | 0.0283 (11) | 0.0144 (9) | 0.0234 (10) | 0.0133 (8) | 0.0088 (9) | 0.0048 (8) |
C152 | 0.0275 (11) | 0.0167 (10) | 0.0229 (11) | 0.0110 (8) | 0.0059 (9) | 0.0028 (8) |
C153 | 0.0375 (12) | 0.0181 (10) | 0.0243 (11) | 0.0133 (9) | 0.0087 (9) | −0.0004 (8) |
C154 | 0.0421 (14) | 0.0264 (12) | 0.0300 (12) | 0.0218 (10) | 0.0156 (10) | 0.0025 (9) |
C155 | 0.0335 (12) | 0.0344 (13) | 0.0355 (13) | 0.0240 (11) | 0.0101 (10) | 0.0058 (10) |
C156 | 0.0314 (12) | 0.0273 (11) | 0.0237 (11) | 0.0186 (9) | 0.0049 (9) | 0.0040 (9) |
N21 | 0.0241 (9) | 0.0145 (8) | 0.0189 (8) | 0.0117 (7) | 0.0048 (7) | 0.0007 (7) |
C211 | 0.0283 (11) | 0.0187 (10) | 0.0216 (10) | 0.0163 (9) | 0.0027 (8) | 0.0011 (8) |
C212 | 0.0310 (11) | 0.0184 (10) | 0.0215 (10) | 0.0146 (9) | 0.0067 (9) | 0.0025 (8) |
O212 | 0.0402 (9) | 0.0160 (7) | 0.0231 (8) | 0.0148 (7) | 0.0092 (7) | 0.0009 (6) |
C213 | 0.0511 (15) | 0.0275 (12) | 0.0315 (13) | 0.0284 (12) | 0.0065 (11) | 0.0046 (10) |
C22 | 0.0260 (10) | 0.0125 (9) | 0.0204 (10) | 0.0108 (8) | 0.0049 (8) | −0.0001 (7) |
C221 | 0.0218 (10) | 0.0197 (10) | 0.0199 (10) | 0.0122 (8) | 0.0032 (8) | 0.0010 (8) |
C222 | 0.0260 (11) | 0.0201 (10) | 0.0241 (11) | 0.0132 (8) | 0.0055 (8) | 0.0019 (8) |
C223 | 0.0265 (11) | 0.0207 (10) | 0.0280 (11) | 0.0115 (9) | 0.0054 (9) | 0.0055 (9) |
C224 | 0.0228 (10) | 0.0279 (12) | 0.0240 (11) | 0.0137 (9) | 0.0048 (8) | 0.0060 (9) |
N224 | 0.0281 (10) | 0.0347 (11) | 0.0289 (10) | 0.0159 (9) | 0.0093 (8) | 0.0099 (9) |
O22 | 0.0342 (9) | 0.0351 (10) | 0.0410 (11) | 0.0093 (8) | 0.0134 (8) | 0.0129 (8) |
O23 | 0.0586 (13) | 0.0499 (13) | 0.0568 (14) | 0.0314 (11) | 0.0390 (11) | 0.0159 (11) |
C225 | 0.0264 (11) | 0.0251 (11) | 0.0249 (11) | 0.0160 (9) | 0.0064 (9) | 0.0028 (9) |
C226 | 0.0278 (11) | 0.0190 (10) | 0.0250 (11) | 0.0141 (9) | 0.0055 (9) | 0.0022 (8) |
N23 | 0.0245 (9) | 0.0161 (8) | 0.0221 (9) | 0.0129 (7) | 0.0061 (7) | 0.0017 (7) |
C24 | 0.0257 (10) | 0.0181 (10) | 0.0197 (10) | 0.0125 (8) | 0.0055 (8) | 0.0001 (8) |
C241 | 0.0248 (10) | 0.0141 (9) | 0.0260 (11) | 0.0112 (8) | 0.0070 (8) | −0.0004 (8) |
C242 | 0.0240 (10) | 0.0191 (10) | 0.0275 (11) | 0.0107 (8) | 0.0065 (9) | 0.0033 (8) |
C243 | 0.0244 (11) | 0.0196 (10) | 0.0388 (13) | 0.0126 (9) | 0.0046 (9) | 0.0032 (9) |
C244 | 0.0261 (11) | 0.0218 (11) | 0.0464 (15) | 0.0127 (9) | 0.0110 (10) | −0.0016 (10) |
C245 | 0.0348 (13) | 0.0279 (12) | 0.0353 (13) | 0.0172 (10) | 0.0164 (10) | −0.0003 (10) |
C246 | 0.0339 (12) | 0.0241 (11) | 0.0266 (11) | 0.0175 (9) | 0.0098 (9) | 0.0015 (9) |
C25 | 0.0253 (10) | 0.0162 (9) | 0.0188 (10) | 0.0123 (8) | 0.0041 (8) | −0.0021 (8) |
C251 | 0.0286 (11) | 0.0165 (10) | 0.0204 (10) | 0.0144 (8) | 0.0082 (8) | 0.0019 (8) |
C252 | 0.0301 (11) | 0.0233 (11) | 0.0257 (11) | 0.0128 (9) | 0.0057 (9) | 0.0001 (9) |
C253 | 0.0321 (12) | 0.0240 (12) | 0.0392 (14) | 0.0112 (10) | 0.0104 (10) | 0.0030 (10) |
C254 | 0.0412 (13) | 0.0238 (11) | 0.0394 (14) | 0.0201 (10) | 0.0211 (11) | 0.0133 (10) |
C255 | 0.0420 (13) | 0.0282 (12) | 0.0244 (11) | 0.0255 (10) | 0.0136 (10) | 0.0095 (9) |
C256 | 0.0319 (11) | 0.0205 (10) | 0.0225 (11) | 0.0176 (9) | 0.0066 (9) | 0.0018 (8) |
N11—C12 | 1.370 (3) | N21—C22 | 1.372 (3) |
N11—C15 | 1.390 (3) | N21—C25 | 1.385 (3) |
N11—C111 | 1.467 (3) | N21—C211 | 1.471 (3) |
C111—C112 | 1.527 (3) | C211—C212 | 1.529 (3) |
C111—H11A | 0.9900 | C211—H21A | 0.9900 |
C111—H11B | 0.9900 | C211—H21B | 0.9900 |
C112—O112 | 1.417 (3) | C212—O212 | 1.414 (3) |
C112—C113 | 1.521 (3) | C212—C213 | 1.521 (3) |
C112—H112 | 1.0000 | C212—H212 | 1.0000 |
O112—H11O | 0.88 (4) | O212—H21O | 0.89 (4) |
C113—H11C | 0.9800 | C213—H21C | 0.9800 |
C113—H11D | 0.9800 | C213—H21D | 0.9800 |
C113—H11E | 0.9800 | C213—H21E | 0.9800 |
C12—N13 | 1.327 (3) | C22—N23 | 1.327 (3) |
C12—C121 | 1.472 (3) | C22—C221 | 1.470 (3) |
C121—C122 | 1.399 (3) | C221—C226 | 1.400 (3) |
C121—C126 | 1.401 (3) | C221—C222 | 1.408 (3) |
C122—C123 | 1.389 (3) | C222—C223 | 1.382 (3) |
C122—H122 | 0.9500 | C222—H222 | 0.9500 |
C123—C124 | 1.382 (3) | C223—C224 | 1.384 (3) |
C123—H123 | 0.9500 | C223—H223 | 0.9500 |
C124—C125 | 1.388 (3) | C224—C225 | 1.387 (3) |
C124—N124 | 1.465 (3) | C224—N224 | 1.465 (3) |
N124—O12 | 1.222 (3) | N224—O23 | 1.224 (3) |
N124—O13 | 1.228 (3) | N224—O22 | 1.230 (3) |
C125—C126 | 1.381 (3) | C225—C226 | 1.390 (3) |
C125—H125 | 0.9500 | C225—H225 | 0.9500 |
C126—H126 | 0.9500 | C226—H226 | 0.9500 |
N13—C14 | 1.374 (3) | N23—C24 | 1.377 (3) |
C14—C15 | 1.379 (3) | C24—C25 | 1.381 (3) |
C14—C141 | 1.479 (3) | C24—C241 | 1.474 (3) |
C141—C142 | 1.391 (3) | C241—C242 | 1.395 (3) |
C141—C146 | 1.391 (3) | C241—C246 | 1.398 (3) |
C142—C143 | 1.392 (3) | C242—C243 | 1.391 (3) |
C142—H142 | 0.9500 | C242—H242 | 0.9500 |
C143—C144 | 1.394 (4) | C243—C244 | 1.380 (4) |
C143—H143 | 0.9500 | C243—H243 | 0.9500 |
C144—C145 | 1.387 (4) | C244—C245 | 1.391 (4) |
C144—H144 | 0.9500 | C244—H244 | 0.9500 |
C145—C146 | 1.389 (3) | C245—C246 | 1.392 (3) |
C145—H145 | 0.9500 | C245—H245 | 0.9500 |
C146—H146 | 0.9500 | C246—H246 | 0.9500 |
C15—C151 | 1.479 (3) | C25—C251 | 1.475 (3) |
C151—C152 | 1.393 (3) | C251—C252 | 1.397 (3) |
C151—C156 | 1.394 (3) | C251—C256 | 1.398 (3) |
C152—C153 | 1.394 (3) | C252—C253 | 1.381 (4) |
C152—H152 | 0.9500 | C252—H252 | 0.9500 |
C153—C154 | 1.383 (4) | C253—C254 | 1.395 (4) |
C153—H153 | 0.9500 | C253—H253 | 0.9500 |
C154—C155 | 1.384 (4) | C254—C255 | 1.386 (4) |
C154—H154 | 0.9500 | C254—H254 | 0.9500 |
C155—C156 | 1.395 (3) | C255—C256 | 1.390 (3) |
C155—H155 | 0.9500 | C255—H255 | 0.9500 |
C156—H156 | 0.9500 | C256—H256 | 0.9500 |
C12—N11—C15 | 107.00 (18) | C22—N21—C25 | 107.17 (17) |
C12—N11—C111 | 128.14 (18) | C22—N21—C211 | 128.44 (18) |
C15—N11—C111 | 124.83 (18) | C25—N21—C211 | 124.28 (18) |
N11—C111—C112 | 112.57 (17) | N21—C211—C212 | 112.49 (18) |
N11—C111—H11A | 109.1 | N21—C211—H21A | 109.1 |
C112—C111—H11A | 109.1 | C212—C211—H21A | 109.1 |
N11—C111—H11B | 109.1 | N21—C211—H21B | 109.1 |
C112—C111—H11B | 109.1 | C212—C211—H21B | 109.1 |
H11A—C111—H11B | 107.8 | H21A—C211—H21B | 107.8 |
O112—C112—C113 | 112.54 (18) | O212—C212—C213 | 113.03 (19) |
O112—C112—C111 | 106.18 (17) | O212—C212—C211 | 106.32 (17) |
C113—C112—C111 | 110.42 (18) | C213—C212—C211 | 110.40 (19) |
O112—C112—H112 | 109.2 | O212—C212—H212 | 109.0 |
C113—C112—H112 | 109.2 | C213—C212—H212 | 109.0 |
C111—C112—H112 | 109.2 | C211—C212—H212 | 109.0 |
C112—O112—H11O | 111 (2) | C212—O212—H21O | 112 (2) |
C112—C113—H11C | 109.5 | C212—C213—H21C | 109.5 |
C112—C113—H11D | 109.5 | C212—C213—H21D | 109.5 |
H11C—C113—H11D | 109.5 | H21C—C213—H21D | 109.5 |
C112—C113—H11E | 109.5 | C212—C213—H21E | 109.5 |
H11C—C113—H11E | 109.5 | H21C—C213—H21E | 109.5 |
H11D—C113—H11E | 109.5 | H21D—C213—H21E | 109.5 |
N13—C12—N11 | 110.95 (19) | N23—C22—N21 | 110.80 (19) |
N13—C12—C121 | 121.03 (19) | N23—C22—C221 | 120.87 (19) |
N11—C12—C121 | 127.94 (19) | N21—C22—C221 | 128.32 (18) |
C122—C121—C126 | 119.1 (2) | C226—C221—C222 | 119.1 (2) |
C122—C121—C12 | 123.53 (19) | C226—C221—C22 | 124.2 (2) |
C126—C121—C12 | 117.30 (19) | C222—C221—C22 | 116.45 (19) |
C123—C122—C121 | 120.2 (2) | C223—C222—C221 | 120.9 (2) |
C123—C122—H122 | 119.9 | C223—C222—H222 | 119.5 |
C121—C122—H122 | 119.9 | C221—C222—H222 | 119.5 |
C124—C123—C122 | 118.9 (2) | C222—C223—C224 | 118.4 (2) |
C124—C123—H123 | 120.6 | C222—C223—H223 | 120.8 |
C122—C123—H123 | 120.6 | C224—C223—H223 | 120.8 |
C123—C124—C125 | 122.4 (2) | C223—C224—C225 | 122.5 (2) |
C123—C124—N124 | 118.6 (2) | C223—C224—N224 | 118.3 (2) |
C125—C124—N124 | 119.0 (2) | C225—C224—N224 | 119.2 (2) |
O12—N124—O13 | 123.5 (2) | O23—N224—O22 | 123.5 (2) |
O12—N124—C124 | 118.4 (2) | O23—N224—C224 | 118.6 (2) |
O13—N124—C124 | 118.1 (2) | O22—N224—C224 | 117.8 (2) |
C126—C125—C124 | 118.1 (2) | C224—C225—C226 | 118.7 (2) |
C126—C125—H125 | 120.9 | C224—C225—H225 | 120.6 |
C124—C125—H125 | 120.9 | C226—C225—H225 | 120.6 |
C125—C126—C121 | 121.2 (2) | C225—C226—C221 | 120.3 (2) |
C125—C126—H126 | 119.4 | C225—C226—H226 | 119.8 |
C121—C126—H126 | 119.4 | C221—C226—H226 | 119.8 |
C12—N13—C14 | 106.47 (18) | C22—N23—C24 | 106.57 (18) |
N13—C14—C15 | 109.86 (19) | N23—C24—C25 | 109.58 (19) |
N13—C14—C141 | 122.40 (19) | N23—C24—C241 | 122.00 (19) |
C15—C14—C141 | 127.7 (2) | C25—C24—C241 | 128.4 (2) |
C142—C141—C146 | 119.1 (2) | C242—C241—C246 | 118.8 (2) |
C142—C141—C14 | 121.0 (2) | C242—C241—C24 | 120.4 (2) |
C146—C141—C14 | 119.9 (2) | C246—C241—C24 | 120.8 (2) |
C141—C142—C143 | 120.2 (2) | C243—C242—C241 | 120.2 (2) |
C141—C142—H142 | 119.9 | C243—C242—H242 | 119.9 |
C143—C142—H142 | 119.9 | C241—C242—H242 | 119.9 |
C142—C143—C144 | 120.2 (2) | C244—C243—C242 | 120.9 (2) |
C142—C143—H143 | 119.9 | C244—C243—H243 | 119.6 |
C144—C143—H143 | 119.9 | C242—C243—H243 | 119.6 |
C145—C144—C143 | 119.7 (2) | C243—C244—C245 | 119.5 (2) |
C145—C144—H144 | 120.1 | C243—C244—H244 | 120.3 |
C143—C144—H144 | 120.1 | C245—C244—H244 | 120.3 |
C144—C145—C146 | 119.8 (2) | C244—C245—C246 | 120.1 (2) |
C144—C145—H145 | 120.1 | C244—C245—H245 | 120.0 |
C146—C145—H145 | 120.1 | C246—C245—H245 | 120.0 |
C145—C146—C141 | 121.0 (2) | C245—C246—C241 | 120.6 (2) |
C145—C146—H146 | 119.5 | C245—C246—H246 | 119.7 |
C141—C146—H146 | 119.5 | C241—C246—H246 | 119.7 |
C14—C15—N11 | 105.72 (19) | C24—C25—N21 | 105.88 (19) |
C14—C15—C151 | 128.9 (2) | C24—C25—C251 | 128.6 (2) |
N11—C15—C151 | 125.36 (19) | N21—C25—C251 | 125.49 (18) |
C152—C151—C156 | 118.9 (2) | C252—C251—C256 | 118.8 (2) |
C152—C151—C15 | 121.9 (2) | C252—C251—C25 | 118.9 (2) |
C156—C151—C15 | 119.0 (2) | C256—C251—C25 | 122.0 (2) |
C151—C152—C153 | 120.2 (2) | C253—C252—C251 | 121.0 (2) |
C151—C152—H152 | 119.9 | C253—C252—H252 | 119.5 |
C153—C152—H152 | 119.9 | C251—C252—H252 | 119.5 |
C154—C153—C152 | 120.5 (2) | C252—C253—C254 | 119.9 (2) |
C154—C153—H153 | 119.8 | C252—C253—H253 | 120.1 |
C152—C153—H153 | 119.7 | C254—C253—H253 | 120.1 |
C153—C154—C155 | 119.7 (2) | C255—C254—C253 | 119.6 (2) |
C153—C154—H154 | 120.2 | C255—C254—H254 | 120.2 |
C155—C154—H154 | 120.2 | C253—C254—H254 | 120.2 |
C154—C155—C156 | 120.1 (2) | C254—C255—C256 | 120.6 (2) |
C154—C155—H155 | 119.9 | C254—C255—H255 | 119.7 |
C156—C155—H155 | 119.9 | C256—C255—H255 | 119.7 |
C151—C156—C155 | 120.6 (2) | C255—C256—C251 | 120.1 (2) |
C151—C156—H156 | 119.7 | C255—C256—H256 | 120.0 |
C155—C156—H156 | 119.7 | C251—C256—H256 | 120.0 |
C12—N11—C111—C112 | −107.9 (2) | C22—N21—C211—C212 | −110.1 (2) |
C15—N11—C111—C112 | 74.2 (2) | C25—N21—C211—C212 | 74.3 (3) |
N11—C111—C112—O112 | 64.7 (2) | N21—C211—C212—O212 | 66.0 (2) |
N11—C111—C112—C113 | −173.05 (19) | N21—C211—C212—C213 | −171.0 (2) |
C15—N11—C12—N13 | 0.4 (2) | C25—N21—C22—N23 | 0.6 (2) |
C111—N11—C12—N13 | −177.80 (18) | C211—N21—C22—N23 | −175.67 (19) |
C15—N11—C12—C121 | 177.1 (2) | C25—N21—C22—C221 | −178.8 (2) |
C111—N11—C12—C121 | −1.1 (3) | C211—N21—C22—C221 | 4.9 (3) |
N13—C12—C121—C122 | −138.1 (2) | N23—C22—C221—C226 | −137.8 (2) |
N11—C12—C121—C122 | 45.5 (3) | N21—C22—C221—C226 | 41.5 (3) |
N13—C12—C121—C126 | 39.2 (3) | N23—C22—C221—C222 | 36.9 (3) |
N11—C12—C121—C126 | −137.1 (2) | N21—C22—C221—C222 | −143.8 (2) |
C126—C121—C122—C123 | 1.0 (3) | C226—C221—C222—C223 | 0.4 (3) |
C12—C121—C122—C123 | 178.3 (2) | C22—C221—C222—C223 | −174.5 (2) |
C121—C122—C123—C124 | 1.2 (4) | C221—C222—C223—C224 | 0.7 (3) |
C122—C123—C124—C125 | −1.7 (4) | C222—C223—C224—C225 | −0.9 (4) |
C122—C123—C124—N124 | 177.6 (2) | C222—C223—C224—N224 | 177.6 (2) |
C123—C124—N124—O12 | 11.7 (4) | C223—C224—N224—O23 | −168.0 (2) |
C125—C124—N124—O12 | −169.0 (3) | C225—C224—N224—O23 | 10.5 (3) |
C123—C124—N124—O13 | −166.8 (3) | C223—C224—N224—O22 | 12.1 (3) |
C125—C124—N124—O13 | 12.5 (4) | C225—C224—N224—O22 | −169.3 (2) |
C123—C124—C125—C126 | −0.2 (4) | C223—C224—C225—C226 | 0.0 (4) |
N124—C124—C125—C126 | −179.5 (2) | N224—C224—C225—C226 | −178.5 (2) |
C124—C125—C126—C121 | 2.4 (4) | C224—C225—C226—C221 | 1.2 (3) |
C122—C121—C126—C125 | −2.9 (4) | C222—C221—C226—C225 | −1.4 (3) |
C12—C121—C126—C125 | 179.6 (2) | C22—C221—C226—C225 | 173.1 (2) |
N11—C12—N13—C14 | −0.3 (2) | N21—C22—N23—C24 | −0.2 (2) |
C121—C12—N13—C14 | −177.24 (19) | C221—C22—N23—C24 | 179.24 (19) |
C12—N13—C14—C15 | 0.0 (2) | C22—N23—C24—C25 | −0.3 (2) |
C12—N13—C14—C141 | 177.4 (2) | C22—N23—C24—C241 | 179.2 (2) |
N13—C14—C141—C142 | 46.6 (3) | N23—C24—C241—C242 | 34.5 (3) |
C15—C14—C141—C142 | −136.5 (2) | C25—C24—C241—C242 | −146.2 (2) |
N13—C14—C141—C146 | −133.2 (2) | N23—C24—C241—C246 | −144.8 (2) |
C15—C14—C141—C146 | 43.6 (3) | C25—C24—C241—C246 | 34.5 (3) |
C146—C141—C142—C143 | −0.9 (3) | C246—C241—C242—C243 | −0.5 (3) |
C14—C141—C142—C143 | 179.3 (2) | C24—C241—C242—C243 | −179.7 (2) |
C141—C142—C143—C144 | 0.7 (4) | C241—C242—C243—C244 | 0.1 (3) |
C142—C143—C144—C145 | 0.1 (4) | C242—C243—C244—C245 | 0.0 (4) |
C143—C144—C145—C146 | −0.7 (4) | C243—C244—C245—C246 | 0.1 (4) |
C144—C145—C146—C141 | 0.5 (4) | C244—C245—C246—C241 | −0.4 (4) |
C142—C141—C146—C145 | 0.3 (3) | C242—C241—C246—C245 | 0.6 (3) |
C14—C141—C146—C145 | −179.9 (2) | C24—C241—C246—C245 | 179.9 (2) |
N13—C14—C15—N11 | 0.2 (2) | N23—C24—C25—N21 | 0.6 (2) |
C141—C14—C15—N11 | −177.0 (2) | C241—C24—C25—N21 | −178.8 (2) |
N13—C14—C15—C151 | −179.5 (2) | N23—C24—C25—C251 | −176.2 (2) |
C141—C14—C15—C151 | 3.4 (4) | C241—C24—C25—C251 | 4.4 (4) |
C12—N11—C15—C14 | −0.4 (2) | C22—N21—C25—C24 | −0.7 (2) |
C111—N11—C15—C14 | 177.92 (18) | C211—N21—C25—C24 | 175.74 (19) |
C12—N11—C15—C151 | 179.31 (19) | C22—N21—C25—C251 | 176.2 (2) |
C111—N11—C15—C151 | −2.4 (3) | C211—N21—C25—C251 | −7.3 (3) |
C14—C15—C151—C152 | −120.2 (3) | C24—C25—C251—C252 | 56.1 (3) |
N11—C15—C151—C152 | 60.2 (3) | N21—C25—C251—C252 | −120.1 (2) |
C14—C15—C151—C156 | 54.2 (3) | C24—C25—C251—C256 | −118.7 (3) |
N11—C15—C151—C156 | −125.4 (2) | N21—C25—C251—C256 | 65.1 (3) |
C156—C151—C152—C153 | 0.9 (3) | C256—C251—C252—C253 | 0.6 (3) |
C15—C151—C152—C153 | 175.3 (2) | C25—C251—C252—C253 | −174.4 (2) |
C151—C152—C153—C154 | −1.2 (3) | C251—C252—C253—C254 | −0.1 (4) |
C152—C153—C154—C155 | 0.7 (4) | C252—C253—C254—C255 | −0.6 (4) |
C153—C154—C155—C156 | 0.2 (4) | C253—C254—C255—C256 | 0.9 (3) |
C152—C151—C156—C155 | 0.0 (3) | C254—C255—C256—C251 | −0.4 (3) |
C15—C151—C156—C155 | −174.6 (2) | C252—C251—C256—C255 | −0.3 (3) |
C154—C155—C156—C151 | −0.5 (4) | C25—C251—C256—C255 | 174.50 (19) |
Cg1 and Cg5 are the centroids of the N11/C12/N13/C14/C15 and N21/C22/N23/C24/C25 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
O212—H21O···N13 | 0.89 (4) | 1.90 (4) | 2.773 (2) | 168 (3) |
C253—H253···O13 | 0.95 | 2.69 | 3.491 (4) | 143 |
O112—H11O···N23i | 0.88 (4) | 1.94 (4) | 2.798 (2) | 165 (3) |
C155—H155···O22i | 0.95 | 2.57 | 3.244 (3) | 128 |
C152—H152···O212ii | 0.95 | 2.66 | 3.263 (3) | 122 |
C153—H153···N21ii | 0.95 | 2.74 | 3.682 (3) | 170 |
C243—H243···O23iii | 0.95 | 2.59 | 3.542 (4) | 176 |
C242—H242···O112iv | 0.95 | 2.71 | 3.338 (3) | 124 |
C256—H256···O112v | 0.95 | 2.57 | 3.208 (3) | 125 |
C145—H145···O22vi | 0.95 | 2.58 | 3.439 (3) | 151 |
C153—H153···Cg5ii | 0.95 | 2.61 | 3.469 (2) | 151 |
C255—H255···Cg1v | 0.95 | 2.66 | 3.544 (3) | 154 |
Symmetry codes: (i) x, y−1, z; (ii) −x+1, −y+1, −z+1; (iii) x−1, y, z; (iv) x, y+1, z; (v) −x+1, −y+1, −z+2; (vi) −x+2, −y+2, −z+1. |
Acknowledgements
We thank the University of Otago for the purchase of the diffractometer. We also thank the Department of Chemistry, University of Otago for the support of the work of JS.
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