research communications
S,3aR,6aS)-3-(1,3-diphenyl-1H-pyrazol-4-yl)-5-(4-methoxyphenyl)-2-phenyl-3,3a,4,5,6,6a-hexahydro-2H-pyrrolo[3,4-d][1,2]oxazole-4,6-dione
and Hirshfeld surface analysis of (3aChemistry and Environmental Division, Manchester Metropolitan University, Manchester, M1 5GD, England, bChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, cChemistry Department, Faculty of Science, Assuit University, Egypt, dDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, eDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, and fFaculty of Science, Department of Bio Chemistry, Beni Suef University, Beni Suef, Egypt
*Correspondence e-mail: shaabankamel@yahoo.com
In the title compound, C33H26N4O4, the two fused five-membered rings and their N-bound aromatic substituents form a pincer-like motif. The relative conformations about the three chiral carbon atoms are established. In the crystal, a combination of C—H⋯O and C—H⋯N hydrogen bonds and C—H⋯π(ring) interactions leads to the formation of layers parallel to the bc plane. A Hirshfeld surface analysis indicates that the most significant contributions to the crystal packing are from H⋯H (44.3%), C⋯H/H⋯C (29.8%) and O⋯H/H⋯O (15.0%) contacts.
Keywords: crystal structure; pyrrole; oxazole; hydrogen bond; C—H⋯π(ring); Hirshfeld surface analysis.
CCDC reference: 2067379
1. Chemical context
Oxazole scaffold compounds currently find application in medicinal drugs such as Aleglitazar (antidiabetic), Ditazole (platelets aggregation inhibitor), Mubritinib (tyrosine kinase inhibitor), and Oxaprozin (COX-2 inhibitor) (Kakkar et al., 2018). In addition they show anti-microbial (Tomi et al., 2015) and anti-cancer (Liu et al., 2009) activity. In this context, we determined the of the title compound.
2. Structural commentary
A puckering analysis of the oxazole fragment (Cremer & Pople, 1975) of the title molecule (Fig. 1) indicates it to have an on N1 with Q(2) = 0.3541 (14) Å and φ(2) = 223.2 (2)°. The pyrrolooxazole fragment is folded along the C2⋯C5 axis by 62.63 (8)° while the dihedral angle between the C2/C3/N2/C4/C5 and C27–C32 rings is 67.11 (8)°. The C9–C14 and C15–C20 rings are inclined to the C6/C7/N3/N4/C8 ring by 32.32 (9) and 33.52 (9)°, respectively.
3. Supramolecular features
In the crystal, the molecules form chains along the c-axis direction through C33—H33A⋯N1 hydrogen bonds. On one side, the chains are connected by C7—H7⋯O3 and C31—H31⋯O3 hydrogen bonds and on the other by inversion-related C29—H29⋯O2 hydrogen bonds, forming layers parallel to the bc plane (Table 1 and Figs. 2 and 3). The layer formation is bolstered by C2—H2⋯Cg5, C23—H23⋯Cg7, C28—H28⋯Cg6 and C32—H32⋯Cg4 interactions (Table 1 and Fig. 4). The diphenylpyrrole groups protrude from both faces of the layers.
4. Hirshfeld surface analysis
A Hirshfeld surface analysis and the associated two-dimensional fingerprint plots were performed with CrystalExplorer17 (Turner et al., 2017) for the identification of the intermolecular interactions in the title compound. Fig. 5(a) and Fig. 5(b) show the front and back sides of the three-dimensional Hirshfeld surface of the title compound plotted over dnorm in the range −0.3067 to 1.6634 a.u. The red spots highlight the interatomic contacts, including the C—H⋯O hydrogen bonds.
The overall two-dimensional fingerprint plot, and those delineated into H⋯H (44.3%), C⋯H/H⋯C (29.8%) and O⋯H/H⋯O (15.0%) contacts (Table 2) are illustrated in Fig. 6a–d, respectively. The other minor contributions to the Hirshfeld surface are by N⋯H/H⋯N (6.5%), C⋯C (1.8%), O⋯C/C⋯O (1.3%), N⋯O/O⋯N (0.5%), O⋯O (0.5%) and N⋯C/C⋯N (0.3%) contacts. The large number of H⋯H, C⋯H/H⋯C and O⋯H/H⋯O interactions suggest that van der Waals interactions and hydrogen bonding play the major roles in the crystal packing (Hathwar et al., 2015).
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5. Database survey
In the R,7aS)-1,3,5,6,7,7a-hexahydro-3-(2-hydroxyphenyl)-1,1-diphenylpyrrolo(1,2-c)(1,3)oxazol-6-ol [CSD Groom et al., 2016) refcode FOMYEM: Shen et al., 2005], the molecules are connected by O—H⋯O and C—H⋯O hydrogen bonds, forming chains along [010]. The chains further interact through C—H⋯O hydrogen bonds, stacking along [100]. In the third direction [001], there are only weak van der Waals interactions, which explains the thin plate habit of the crystals.
of the related compound (66. Synthesis and crystallization
A mixture of N-(4-methoxyphenyl) maleimide (0.6 g, 3 mmol) and (Z)-N-[(1,3-diphenyl-1H-pyrazol-4-yl)methylene]benzenamine oxide (1.1 g, 3 mmol) in toluene (15 ml) was heated at 373 K under reflux for 24 h, the reaction was monitored by TLC. The endo isomer was filtered off as a major product. The title compound was recrystallized from a mixture of toluene and petroleum ether as colorless crystals in 60% yield; mp: 469–471 K.
7. Refinement
Crystal data, data collection and structure . H atoms on C atoms were located in a difference-Fourier map and were freely refined.
details are summarized in Table 3
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Supporting information
CCDC reference: 2067379
https://doi.org/10.1107/S2056989021002358/ex2041sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989021002358/ex2041Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989021002358/ex2041Isup3.cml
Data collection: APEX3 (Bruker, 2016); cell
SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016/6 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).C33H26N4O4 | Z = 2 |
Mr = 542.58 | F(000) = 568 |
Triclinic, P1 | Dx = 1.353 Mg m−3 |
a = 11.5014 (3) Å | Cu Kα radiation, λ = 1.54178 Å |
b = 11.5340 (3) Å | Cell parameters from 8367 reflections |
c = 11.7878 (3) Å | θ = 4.0–72.0° |
α = 73.567 (1)° | µ = 0.73 mm−1 |
β = 74.613 (1)° | T = 150 K |
γ = 64.218 (1)° | Block, colourless |
V = 1332.10 (6) Å3 | 0.13 × 0.11 × 0.05 mm |
Bruker D8 VENTURE PHOTON 100 CMOS diffractometer | 4940 independent reflections |
Radiation source: INCOATEC IµS micro–focus source | 4357 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.027 |
Detector resolution: 10.4167 pixels mm-1 | θmax = 72.0°, θmin = 4.0° |
ω scans | h = −14→14 |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | k = −14→13 |
Tmin = 0.86, Tmax = 0.96 | l = −13→14 |
10211 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.037 | All H-atom parameters refined |
wR(F2) = 0.098 | w = 1/[σ2(Fo2) + (0.0455P)2 + 0.394P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
4940 reflections | Δρmax = 0.23 e Å−3 |
475 parameters | Δρmin = −0.20 e Å−3 |
0 restraints | Extinction correction: SHELXL 2016/6 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0058 (5) |
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. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.46877 (9) | 0.14792 (8) | 0.46118 (8) | 0.0270 (2) | |
O2 | 0.26199 (10) | 0.45329 (9) | 0.17596 (9) | 0.0302 (2) | |
O3 | 0.52260 (10) | 0.01734 (9) | 0.25051 (9) | 0.0336 (2) | |
O4 | 0.67552 (11) | 0.26355 (11) | −0.28302 (9) | 0.0390 (3) | |
N1 | 0.46935 (11) | 0.27693 (10) | 0.44250 (10) | 0.0245 (2) | |
N2 | 0.40487 (11) | 0.23670 (10) | 0.18438 (10) | 0.0236 (2) | |
N3 | 0.18502 (11) | 0.33463 (10) | 0.75289 (10) | 0.0246 (2) | |
N4 | 0.10816 (10) | 0.46224 (10) | 0.71745 (10) | 0.0243 (2) | |
C1 | 0.33181 (12) | 0.36685 (12) | 0.43619 (11) | 0.0228 (3) | |
H1 | 0.3304 (15) | 0.4527 (15) | 0.3909 (13) | 0.024 (4)* | |
C2 | 0.28461 (13) | 0.30151 (12) | 0.36855 (12) | 0.0245 (3) | |
H2 | 0.1901 (16) | 0.3188 (15) | 0.3945 (13) | 0.026 (4)* | |
C3 | 0.31112 (12) | 0.34491 (12) | 0.23320 (12) | 0.0238 (3) | |
C4 | 0.44410 (13) | 0.12338 (12) | 0.27068 (12) | 0.0258 (3) | |
C5 | 0.37528 (13) | 0.15754 (13) | 0.39352 (12) | 0.0265 (3) | |
H5 | 0.3347 (16) | 0.0972 (15) | 0.4409 (14) | 0.028 (4)* | |
C6 | 0.25513 (12) | 0.37807 (12) | 0.55967 (12) | 0.0235 (3) | |
C7 | 0.27413 (13) | 0.28120 (13) | 0.66093 (12) | 0.0256 (3) | |
H7 | 0.3367 (15) | 0.1930 (15) | 0.6739 (13) | 0.022 (4)* | |
C8 | 0.14996 (12) | 0.48910 (12) | 0.59946 (11) | 0.0228 (3) | |
C9 | 0.16696 (12) | 0.27185 (13) | 0.87539 (12) | 0.0253 (3) | |
C10 | 0.19210 (14) | 0.13870 (14) | 0.90401 (13) | 0.0289 (3) | |
H10 | 0.2233 (16) | 0.0892 (15) | 0.8422 (14) | 0.028 (4)* | |
C11 | 0.17540 (14) | 0.07874 (15) | 1.02412 (14) | 0.0345 (3) | |
H11 | 0.1937 (18) | −0.0118 (19) | 1.0384 (16) | 0.044 (5)* | |
C12 | 0.13366 (14) | 0.15145 (16) | 1.11359 (13) | 0.0355 (3) | |
H12 | 0.1232 (18) | 0.1059 (18) | 1.1967 (17) | 0.044 (5)* | |
C13 | 0.10923 (14) | 0.28455 (15) | 1.08380 (13) | 0.0331 (3) | |
H13 | 0.0795 (18) | 0.3375 (17) | 1.1455 (16) | 0.043 (5)* | |
C14 | 0.12613 (13) | 0.34511 (14) | 0.96421 (12) | 0.0281 (3) | |
H14 | 0.1116 (16) | 0.4389 (17) | 0.9412 (14) | 0.034 (4)* | |
C15 | 0.08571 (12) | 0.62188 (12) | 0.53116 (12) | 0.0241 (3) | |
C16 | 0.03690 (14) | 0.72978 (13) | 0.58761 (13) | 0.0285 (3) | |
H16 | 0.0510 (16) | 0.7157 (15) | 0.6670 (15) | 0.028 (4)* | |
C17 | −0.02833 (15) | 0.85474 (14) | 0.52723 (15) | 0.0351 (3) | |
H17 | −0.0626 (18) | 0.9299 (18) | 0.5673 (15) | 0.041 (5)* | |
C18 | −0.04373 (15) | 0.87516 (15) | 0.40921 (15) | 0.0386 (4) | |
H18 | −0.088 (2) | 0.962 (2) | 0.3644 (17) | 0.052 (5)* | |
C19 | 0.00554 (15) | 0.76944 (15) | 0.35259 (14) | 0.0361 (3) | |
H19 | −0.0036 (18) | 0.7840 (17) | 0.2689 (17) | 0.043 (5)* | |
C20 | 0.06899 (13) | 0.64321 (14) | 0.41334 (13) | 0.0289 (3) | |
H20 | 0.1000 (16) | 0.5690 (16) | 0.3741 (15) | 0.032 (4)* | |
C21 | 0.56878 (12) | 0.29685 (13) | 0.34556 (12) | 0.0250 (3) | |
C22 | 0.56937 (14) | 0.42275 (14) | 0.30470 (14) | 0.0318 (3) | |
H22 | 0.5019 (17) | 0.4971 (17) | 0.3399 (15) | 0.033 (4)* | |
C23 | 0.66806 (15) | 0.44335 (16) | 0.21469 (15) | 0.0373 (3) | |
H23 | 0.6673 (18) | 0.5311 (19) | 0.1846 (16) | 0.043 (5)* | |
C24 | 0.76798 (14) | 0.33984 (16) | 0.16605 (15) | 0.0375 (3) | |
H24 | 0.838 (2) | 0.3552 (18) | 0.1016 (17) | 0.049 (5)* | |
C25 | 0.76971 (14) | 0.21467 (15) | 0.20983 (14) | 0.0347 (3) | |
H25 | 0.8426 (18) | 0.1395 (18) | 0.1773 (16) | 0.040 (5)* | |
C26 | 0.67152 (13) | 0.19190 (14) | 0.29954 (13) | 0.0295 (3) | |
H26 | 0.6735 (17) | 0.1023 (17) | 0.3297 (15) | 0.035 (4)* | |
C27 | 0.46908 (12) | 0.24495 (12) | 0.06130 (11) | 0.0233 (3) | |
C28 | 0.54580 (14) | 0.31853 (13) | 0.01970 (12) | 0.0279 (3) | |
H28 | 0.5515 (17) | 0.3678 (17) | 0.0727 (16) | 0.038 (4)* | |
C29 | 0.61394 (14) | 0.32202 (14) | −0.09549 (13) | 0.0310 (3) | |
H29 | 0.6701 (17) | 0.3686 (17) | −0.1243 (15) | 0.037 (4)* | |
C30 | 0.60485 (13) | 0.25230 (13) | −0.16986 (12) | 0.0281 (3) | |
C31 | 0.52736 (13) | 0.17974 (13) | −0.12874 (12) | 0.0272 (3) | |
H31 | 0.5212 (16) | 0.1302 (16) | −0.1811 (15) | 0.033 (4)* | |
C32 | 0.45934 (13) | 0.17575 (13) | −0.01174 (12) | 0.0251 (3) | |
H32 | 0.4043 (16) | 0.1249 (15) | 0.0197 (14) | 0.026 (4)* | |
C33 | 0.67512 (19) | 0.1895 (2) | −0.36073 (16) | 0.0462 (4) | |
H33A | 0.587 (2) | 0.219 (2) | −0.3788 (19) | 0.063 (6)* | |
H33B | 0.710 (2) | 0.090 (2) | −0.3253 (19) | 0.062 (6)* | |
H33C | 0.731 (2) | 0.209 (2) | −0.4359 (19) | 0.056 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0298 (5) | 0.0207 (4) | 0.0256 (5) | −0.0064 (4) | −0.0054 (4) | −0.0018 (4) |
O2 | 0.0324 (5) | 0.0225 (5) | 0.0320 (5) | −0.0048 (4) | −0.0113 (4) | −0.0039 (4) |
O3 | 0.0408 (6) | 0.0213 (5) | 0.0303 (5) | −0.0045 (4) | −0.0039 (4) | −0.0070 (4) |
O4 | 0.0393 (6) | 0.0507 (7) | 0.0265 (5) | −0.0213 (5) | 0.0036 (5) | −0.0087 (5) |
N1 | 0.0233 (5) | 0.0207 (5) | 0.0256 (6) | −0.0052 (4) | −0.0043 (4) | −0.0041 (4) |
N2 | 0.0254 (5) | 0.0220 (5) | 0.0219 (6) | −0.0075 (4) | −0.0032 (4) | −0.0056 (4) |
N3 | 0.0244 (5) | 0.0212 (5) | 0.0224 (6) | −0.0050 (4) | −0.0017 (4) | −0.0040 (4) |
N4 | 0.0231 (5) | 0.0218 (5) | 0.0244 (6) | −0.0057 (4) | −0.0032 (4) | −0.0048 (4) |
C1 | 0.0214 (6) | 0.0211 (6) | 0.0221 (6) | −0.0048 (5) | −0.0033 (5) | −0.0044 (5) |
C2 | 0.0218 (6) | 0.0245 (7) | 0.0250 (7) | −0.0069 (5) | −0.0019 (5) | −0.0067 (5) |
C3 | 0.0220 (6) | 0.0224 (6) | 0.0276 (7) | −0.0071 (5) | −0.0063 (5) | −0.0062 (5) |
C4 | 0.0286 (7) | 0.0221 (6) | 0.0263 (7) | −0.0100 (5) | −0.0041 (5) | −0.0044 (5) |
C5 | 0.0291 (7) | 0.0232 (6) | 0.0256 (7) | −0.0105 (6) | −0.0019 (6) | −0.0041 (5) |
C6 | 0.0227 (6) | 0.0225 (6) | 0.0232 (6) | −0.0066 (5) | −0.0023 (5) | −0.0062 (5) |
C7 | 0.0255 (6) | 0.0224 (7) | 0.0234 (7) | −0.0049 (5) | −0.0010 (5) | −0.0061 (5) |
C8 | 0.0221 (6) | 0.0220 (6) | 0.0237 (6) | −0.0075 (5) | −0.0031 (5) | −0.0062 (5) |
C9 | 0.0208 (6) | 0.0268 (7) | 0.0240 (7) | −0.0074 (5) | −0.0026 (5) | −0.0024 (5) |
C10 | 0.0273 (7) | 0.0271 (7) | 0.0283 (7) | −0.0083 (5) | −0.0041 (6) | −0.0038 (6) |
C11 | 0.0282 (7) | 0.0302 (8) | 0.0356 (8) | −0.0083 (6) | −0.0051 (6) | 0.0024 (6) |
C12 | 0.0273 (7) | 0.0434 (9) | 0.0257 (7) | −0.0110 (6) | −0.0023 (6) | 0.0019 (6) |
C13 | 0.0236 (6) | 0.0436 (8) | 0.0263 (7) | −0.0091 (6) | 0.0000 (6) | −0.0088 (6) |
C14 | 0.0230 (6) | 0.0298 (7) | 0.0275 (7) | −0.0077 (5) | −0.0003 (5) | −0.0072 (5) |
C15 | 0.0191 (6) | 0.0227 (6) | 0.0276 (7) | −0.0064 (5) | −0.0023 (5) | −0.0051 (5) |
C16 | 0.0284 (7) | 0.0255 (7) | 0.0289 (7) | −0.0103 (6) | 0.0002 (6) | −0.0060 (5) |
C17 | 0.0313 (7) | 0.0218 (7) | 0.0439 (9) | −0.0061 (6) | −0.0002 (6) | −0.0066 (6) |
C18 | 0.0310 (7) | 0.0262 (7) | 0.0467 (9) | −0.0049 (6) | −0.0104 (7) | 0.0040 (6) |
C19 | 0.0314 (7) | 0.0390 (8) | 0.0339 (8) | −0.0103 (6) | −0.0133 (6) | 0.0008 (6) |
C20 | 0.0240 (6) | 0.0301 (7) | 0.0314 (7) | −0.0074 (5) | −0.0071 (6) | −0.0068 (6) |
C21 | 0.0212 (6) | 0.0284 (7) | 0.0240 (6) | −0.0072 (5) | −0.0069 (5) | −0.0039 (5) |
C22 | 0.0249 (7) | 0.0302 (7) | 0.0404 (8) | −0.0098 (6) | −0.0064 (6) | −0.0075 (6) |
C23 | 0.0283 (7) | 0.0354 (8) | 0.0483 (9) | −0.0157 (6) | −0.0081 (7) | −0.0013 (7) |
C24 | 0.0238 (7) | 0.0463 (9) | 0.0398 (9) | −0.0157 (6) | −0.0042 (6) | −0.0021 (7) |
C25 | 0.0219 (7) | 0.0401 (8) | 0.0354 (8) | −0.0068 (6) | −0.0023 (6) | −0.0084 (6) |
C26 | 0.0226 (6) | 0.0290 (7) | 0.0310 (7) | −0.0048 (5) | −0.0057 (6) | −0.0044 (6) |
C27 | 0.0231 (6) | 0.0228 (6) | 0.0209 (6) | −0.0060 (5) | −0.0039 (5) | −0.0043 (5) |
C28 | 0.0322 (7) | 0.0268 (7) | 0.0274 (7) | −0.0127 (6) | −0.0078 (6) | −0.0045 (5) |
C29 | 0.0332 (7) | 0.0310 (7) | 0.0312 (7) | −0.0173 (6) | −0.0061 (6) | −0.0007 (6) |
C30 | 0.0259 (6) | 0.0300 (7) | 0.0224 (7) | −0.0077 (5) | −0.0028 (5) | −0.0026 (5) |
C31 | 0.0274 (7) | 0.0284 (7) | 0.0258 (7) | −0.0083 (5) | −0.0053 (6) | −0.0086 (5) |
C32 | 0.0236 (6) | 0.0236 (6) | 0.0280 (7) | −0.0084 (5) | −0.0047 (5) | −0.0055 (5) |
C33 | 0.0416 (9) | 0.0681 (13) | 0.0281 (8) | −0.0206 (9) | 0.0018 (7) | −0.0166 (8) |
O1—N1 | 1.4440 (14) | C14—H14 | 0.986 (17) |
O1—C5 | 1.4511 (16) | C15—C20 | 1.3905 (19) |
O2—C3 | 1.2032 (16) | C15—C16 | 1.4034 (18) |
O3—C4 | 1.2073 (16) | C16—C17 | 1.382 (2) |
O4—C30 | 1.3694 (17) | C16—H16 | 0.949 (16) |
O4—C33 | 1.420 (2) | C17—C18 | 1.390 (2) |
N1—C21 | 1.4329 (17) | C17—H17 | 0.982 (18) |
N1—C1 | 1.4748 (16) | C18—C19 | 1.383 (2) |
N2—C4 | 1.3875 (17) | C18—H18 | 0.97 (2) |
N2—C3 | 1.3993 (16) | C19—C20 | 1.389 (2) |
N2—C27 | 1.4400 (17) | C19—H19 | 0.978 (19) |
N3—N4 | 1.3559 (15) | C20—H20 | 0.972 (17) |
N3—C7 | 1.3580 (17) | C21—C26 | 1.3939 (19) |
N3—C9 | 1.4257 (16) | C21—C22 | 1.397 (2) |
N4—C8 | 1.3389 (17) | C22—C23 | 1.387 (2) |
C1—C6 | 1.4965 (18) | C22—H22 | 0.981 (17) |
C1—C2 | 1.5570 (17) | C23—C24 | 1.385 (2) |
C1—H1 | 0.978 (16) | C23—H23 | 0.970 (19) |
C2—C5 | 1.5204 (18) | C24—C25 | 1.382 (2) |
C2—C3 | 1.5205 (18) | C24—H24 | 0.99 (2) |
C2—H2 | 0.992 (16) | C25—C26 | 1.389 (2) |
C4—C5 | 1.5237 (19) | C25—H25 | 0.994 (18) |
C5—H5 | 0.969 (16) | C26—H26 | 0.985 (17) |
C6—C7 | 1.3757 (19) | C27—C32 | 1.3815 (18) |
C6—C8 | 1.4192 (17) | C27—C28 | 1.3877 (19) |
C7—H7 | 0.954 (15) | C28—C29 | 1.375 (2) |
C8—C15 | 1.4742 (18) | C28—H28 | 0.986 (18) |
C9—C14 | 1.3874 (19) | C29—C30 | 1.395 (2) |
C9—C10 | 1.3886 (19) | C29—H29 | 0.950 (18) |
C10—C11 | 1.392 (2) | C30—C31 | 1.386 (2) |
C10—H10 | 0.951 (16) | C31—C32 | 1.393 (2) |
C11—C12 | 1.388 (2) | C31—H31 | 0.985 (17) |
C11—H11 | 0.945 (19) | C32—H32 | 0.979 (16) |
C12—C13 | 1.390 (2) | C33—H33A | 0.98 (2) |
C12—H12 | 0.976 (19) | C33—H33B | 1.03 (2) |
C13—C14 | 1.389 (2) | C33—H33C | 0.98 (2) |
C13—H13 | 0.978 (18) | ||
N1—O1—C5 | 107.88 (9) | C13—C14—H14 | 121.2 (9) |
C30—O4—C33 | 117.49 (12) | C20—C15—C16 | 118.93 (13) |
C21—N1—O1 | 112.08 (10) | C20—C15—C8 | 121.98 (12) |
C21—N1—C1 | 118.58 (10) | C16—C15—C8 | 119.08 (12) |
O1—N1—C1 | 104.26 (9) | C17—C16—C15 | 120.27 (14) |
C4—N2—C3 | 112.73 (11) | C17—C16—H16 | 120.8 (9) |
C4—N2—C27 | 122.68 (11) | C15—C16—H16 | 119.0 (9) |
C3—N2—C27 | 123.94 (10) | C16—C17—C18 | 120.35 (14) |
N4—N3—C7 | 112.51 (11) | C16—C17—H17 | 119.9 (10) |
N4—N3—C9 | 120.07 (10) | C18—C17—H17 | 119.7 (10) |
C7—N3—C9 | 127.42 (11) | C19—C18—C17 | 119.65 (14) |
C8—N4—N3 | 104.61 (10) | C19—C18—H18 | 118.2 (12) |
N1—C1—C6 | 110.28 (10) | C17—C18—H18 | 122.2 (12) |
N1—C1—C2 | 103.54 (10) | C18—C19—C20 | 120.39 (14) |
C6—C1—C2 | 112.28 (11) | C18—C19—H19 | 119.6 (11) |
N1—C1—H1 | 108.2 (9) | C20—C19—H19 | 120.0 (11) |
C6—C1—H1 | 110.3 (9) | C19—C20—C15 | 120.39 (13) |
C2—C1—H1 | 112.0 (9) | C19—C20—H20 | 119.9 (10) |
C5—C2—C3 | 105.11 (10) | C15—C20—H20 | 119.7 (10) |
C5—C2—C1 | 103.42 (10) | C26—C21—C22 | 119.39 (13) |
C3—C2—C1 | 112.44 (10) | C26—C21—N1 | 121.46 (12) |
C5—C2—H2 | 114.6 (9) | C22—C21—N1 | 118.85 (12) |
C3—C2—H2 | 109.0 (9) | C23—C22—C21 | 119.91 (14) |
C1—C2—H2 | 112.1 (9) | C23—C22—H22 | 119.0 (10) |
O2—C3—N2 | 124.77 (12) | C21—C22—H22 | 121.0 (10) |
O2—C3—C2 | 126.87 (12) | C24—C23—C22 | 120.74 (14) |
N2—C3—C2 | 108.36 (10) | C24—C23—H23 | 119.2 (11) |
O3—C4—N2 | 125.05 (13) | C22—C23—H23 | 120.0 (11) |
O3—C4—C5 | 126.56 (12) | C25—C24—C23 | 119.17 (14) |
N2—C4—C5 | 108.36 (11) | C25—C24—H24 | 120.5 (11) |
O1—C5—C2 | 106.71 (10) | C23—C24—H24 | 120.4 (11) |
O1—C5—C4 | 110.42 (11) | C24—C25—C26 | 121.04 (14) |
C2—C5—C4 | 105.31 (11) | C24—C25—H25 | 119.7 (10) |
O1—C5—H5 | 106.3 (9) | C26—C25—H25 | 119.3 (10) |
C2—C5—H5 | 116.3 (9) | C25—C26—C21 | 119.67 (13) |
C4—C5—H5 | 111.7 (9) | C25—C26—H26 | 120.3 (10) |
C7—C6—C8 | 104.76 (11) | C21—C26—H26 | 120.0 (10) |
C7—C6—C1 | 126.68 (11) | C32—C27—C28 | 120.90 (12) |
C8—C6—C1 | 128.55 (12) | C32—C27—N2 | 120.45 (12) |
N3—C7—C6 | 106.86 (11) | C28—C27—N2 | 118.57 (11) |
N3—C7—H7 | 121.3 (9) | C29—C28—C27 | 119.68 (12) |
C6—C7—H7 | 131.8 (9) | C29—C28—H28 | 120.3 (10) |
N4—C8—C6 | 111.26 (11) | C27—C28—H28 | 120.0 (10) |
N4—C8—C15 | 118.98 (11) | C28—C29—C30 | 119.83 (13) |
C6—C8—C15 | 129.76 (12) | C28—C29—H29 | 120.8 (10) |
C14—C9—C10 | 121.14 (13) | C30—C29—H29 | 119.3 (10) |
C14—C9—N3 | 119.11 (12) | O4—C30—C31 | 124.41 (13) |
C10—C9—N3 | 119.75 (12) | O4—C30—C29 | 115.05 (12) |
C9—C10—C11 | 118.96 (13) | C31—C30—C29 | 120.53 (13) |
C9—C10—H10 | 120.1 (9) | C30—C31—C32 | 119.40 (12) |
C11—C10—H10 | 120.9 (10) | C30—C31—H31 | 120.6 (10) |
C12—C11—C10 | 120.31 (14) | C32—C31—H31 | 120.0 (10) |
C12—C11—H11 | 124.3 (11) | C27—C32—C31 | 119.65 (12) |
C10—C11—H11 | 115.4 (11) | C27—C32—H32 | 119.3 (9) |
C11—C12—C13 | 120.17 (14) | C31—C32—H32 | 121.1 (9) |
C11—C12—H12 | 117.9 (11) | O4—C33—H33A | 110.8 (13) |
C13—C12—H12 | 121.9 (11) | O4—C33—H33B | 111.9 (12) |
C14—C13—C12 | 119.92 (14) | H33A—C33—H33B | 109.9 (18) |
C14—C13—H13 | 118.7 (11) | O4—C33—H33C | 105.6 (12) |
C12—C13—H13 | 121.4 (11) | H33A—C33—H33C | 107.3 (17) |
C9—C14—C13 | 119.49 (13) | H33B—C33—H33C | 111.2 (17) |
C9—C14—H14 | 119.3 (9) | ||
C5—O1—N1—C21 | −93.40 (11) | N4—N3—C9—C10 | 148.20 (12) |
C5—O1—N1—C1 | 36.07 (12) | C7—N3—C9—C10 | −31.9 (2) |
C7—N3—N4—C8 | 0.44 (14) | C14—C9—C10—C11 | 0.2 (2) |
C9—N3—N4—C8 | −179.62 (11) | N3—C9—C10—C11 | 179.26 (12) |
C21—N1—C1—C6 | −151.26 (11) | C9—C10—C11—C12 | 0.3 (2) |
O1—N1—C1—C6 | 83.28 (11) | C10—C11—C12—C13 | −0.5 (2) |
C21—N1—C1—C2 | 88.43 (13) | C11—C12—C13—C14 | 0.2 (2) |
O1—N1—C1—C2 | −37.03 (12) | C10—C9—C14—C13 | −0.4 (2) |
N1—C1—C2—C5 | 24.76 (12) | N3—C9—C14—C13 | −179.52 (12) |
C6—C1—C2—C5 | −94.18 (12) | C12—C13—C14—C9 | 0.2 (2) |
N1—C1—C2—C3 | −88.10 (12) | N4—C8—C15—C20 | −145.50 (13) |
C6—C1—C2—C3 | 152.95 (11) | C6—C8—C15—C20 | 34.8 (2) |
C4—N2—C3—O2 | −179.52 (12) | N4—C8—C15—C16 | 32.83 (18) |
C27—N2—C3—O2 | 9.52 (19) | C6—C8—C15—C16 | −146.91 (14) |
C4—N2—C3—C2 | 1.03 (14) | C20—C15—C16—C17 | 0.9 (2) |
C27—N2—C3—C2 | −169.93 (11) | C8—C15—C16—C17 | −177.43 (12) |
C5—C2—C3—O2 | −178.08 (13) | C15—C16—C17—C18 | −1.4 (2) |
C1—C2—C3—O2 | −66.26 (17) | C16—C17—C18—C19 | 0.6 (2) |
C5—C2—C3—N2 | 1.36 (13) | C17—C18—C19—C20 | 0.6 (2) |
C1—C2—C3—N2 | 113.18 (11) | C18—C19—C20—C15 | −1.1 (2) |
C3—N2—C4—O3 | 179.04 (13) | C16—C15—C20—C19 | 0.3 (2) |
C27—N2—C4—O3 | −9.9 (2) | C8—C15—C20—C19 | 178.64 (13) |
C3—N2—C4—C5 | −3.01 (15) | O1—N1—C21—C26 | −15.87 (16) |
C27—N2—C4—C5 | 168.09 (11) | C1—N1—C21—C26 | −137.45 (12) |
N1—O1—C5—C2 | −19.58 (12) | O1—N1—C21—C22 | 170.53 (11) |
N1—O1—C5—C4 | 94.36 (11) | C1—N1—C21—C22 | 48.95 (16) |
C3—C2—C5—O1 | 114.40 (11) | C26—C21—C22—C23 | 3.3 (2) |
C1—C2—C5—O1 | −3.69 (13) | N1—C21—C22—C23 | 177.07 (13) |
C3—C2—C5—C4 | −2.97 (13) | C21—C22—C23—C24 | −1.2 (2) |
C1—C2—C5—C4 | −121.07 (11) | C22—C23—C24—C25 | −1.2 (2) |
O3—C4—C5—O1 | 66.77 (17) | C23—C24—C25—C26 | 1.5 (2) |
N2—C4—C5—O1 | −111.15 (11) | C24—C25—C26—C21 | 0.6 (2) |
O3—C4—C5—C2 | −178.40 (13) | C22—C21—C26—C25 | −3.0 (2) |
N2—C4—C5—C2 | 3.68 (14) | N1—C21—C26—C25 | −176.59 (12) |
N1—C1—C6—C7 | −33.17 (18) | C4—N2—C27—C32 | 68.77 (17) |
C2—C1—C6—C7 | 81.74 (16) | C3—N2—C27—C32 | −121.14 (14) |
N1—C1—C6—C8 | 145.50 (13) | C4—N2—C27—C28 | −108.13 (14) |
C2—C1—C6—C8 | −99.60 (15) | C3—N2—C27—C28 | 61.95 (17) |
N4—N3—C7—C6 | −0.12 (15) | C32—C27—C28—C29 | −0.5 (2) |
C9—N3—C7—C6 | 179.94 (12) | N2—C27—C28—C29 | 176.40 (12) |
C8—C6—C7—N3 | −0.22 (14) | C27—C28—C29—C30 | 0.4 (2) |
C1—C6—C7—N3 | 178.70 (12) | C33—O4—C30—C31 | −3.9 (2) |
N3—N4—C8—C6 | −0.58 (14) | C33—O4—C30—C29 | 176.95 (14) |
N3—N4—C8—C15 | 179.64 (11) | C28—C29—C30—O4 | 179.37 (12) |
C7—C6—C8—N4 | 0.51 (15) | C28—C29—C30—C31 | 0.2 (2) |
C1—C6—C8—N4 | −178.38 (12) | O4—C30—C31—C32 | −179.77 (12) |
C7—C6—C8—C15 | −179.73 (13) | C29—C30—C31—C32 | −0.7 (2) |
C1—C6—C8—C15 | 1.4 (2) | C28—C27—C32—C31 | 0.0 (2) |
N4—N3—C9—C14 | −32.70 (18) | N2—C27—C32—C31 | −176.82 (11) |
C7—N3—C9—C14 | 147.23 (13) | C30—C31—C32—C27 | 0.6 (2) |
Cg4, Cg5, Cg6 and Cg7 are the centroids of the C9–C14, C15–C20, C21–C26 and C27–C32 benzene rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···Cg5i | 0.992 (16) | 2.817 (19) | 3.7292 (17) | 153.2 (12) |
C7—H7···O3ii | 0.954 (15) | 2.329 (15) | 3.2666 (16) | 167.4 (12) |
C22—H22···O4iii | 0.981 (17) | 2.648 (17) | 3.4762 (18) | 142.3 (13) |
C23—H23···Cg7iii | 0.970 (19) | 2.97 (2) | 3.6086 (18) | 124.2 (16) |
C28—H28···Cg6 | 0.986 (18) | 2.66 (2) | 3.4522 (17) | 138.1 (14) |
C29—H29···O2iii | 0.950 (18) | 2.374 (18) | 3.2803 (17) | 159.3 (14) |
C31—H31···O3iv | 0.985 (17) | 2.360 (17) | 3.3133 (17) | 162.5 (14) |
C32—H32···Cg4v | 0.979 (16) | 2.71 (2) | 3.3750 (18) | 125.3 (12) |
C33—H33A···N1v | 0.98 (2) | 2.58 (2) | 3.393 (2) | 140.6 (17) |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y, −z+1; (iii) −x+1, −y+1, −z; (iv) −x+1, −y, −z; (v) x, y, z−1. |
Contact | Distance | Symmetry operation |
H7···O3 | 2.33 | 1 - x, -y, 1 - z |
H29···O2 | 2.37 | 1 - x, 1 - y, -z |
H31···O3 | 2.36 | 1 - x, -y, -z |
N1···H33A | 2.58 | x, y, 1 + z |
H16···H13 | 2.41 | -x, 1 - y, 2 - z |
H2···C16 | 2.84 | -x, 1 - y, 1 - z |
C13···H24 | 2.82 | -1 + x, y, 1 + z |
H17···H17 | 2.56 | -x, 2 - y, 1 - z |
H24···H14 | 2.57 | 1 - x, 1 - y, 1 - z |
Funding information
The support of NSF–MRI grant No. 1228232 for the purchase of the diffractometer and Tulane University for support of the Tulane Crystallography Laboratory are gratefully acknowledged.
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