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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoIUCrDATA
ISSN: 2414-3146
Volume 1| Part 11| November 2016| x161884
https://doi.org/10.1107/S2414314616018848

Ethyl 8-amino-7-(furan-2-yl)-5,6-di­hydrothieno[2,3-b]benzo[h]quinoline-9-carboxyl­ate

CROSSMARK_Color_square_no_text.svg
Etify A. Bakhite,a Manpreet Kaur,b Mehmet Akkurt,c Shaaban K. Mohamed,d,e Jerry P. Jasinskib and Mustafa R. Albayatif*

aChemistry Department, Faculty of Science, Assiut University, 71516 Assiut, Egypt, bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, cDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, dChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, eChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, and fKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
*Correspondence e-mail: shaabankamel@yahoo.com

Edited by P. Bombicz, Hungarian Academy of Sciences, Hungary (Received 30 September 2016; accepted 24 November 2016; online 29 November 2016)

In the title compound, C22H18N2O3S, the two independent mol­ecules in the asymmetric unit form a dimer via N—H⋯O hydrogen bonds. In the crystal, the mol­ecular layers can be found in the (110) plane, connected by C—H⋯π inter­actions. Atoms of the furan ring of one independent mol­ecule are disordered over two sets of sites with an occupancy ratio 0.735 (3):0.265 (3).

CCDC reference: 1519100

Similar articles
3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

The thio­phene moiety is present in a large number of bioactive mol­ecules having diverse biological activities such as anti-inflammatory (Murakami et al., 1998[Murakami, N., Takase, H., Saito, T., Iwata, K., Miura, H. & Naruse, T. (1998). Eur. J. Pharmacol. 352, 81-90.]), anti­convulsant (Kulandasamy et al., 2009[Kulandasamy, R., Adhikari, A. V. & Stables, J. P. (2009). Eur. J. Med. Chem. 44, 4376-4384.]), anti­bacterial (Lu et al., 2011[Lu, X., Wan, B., Franzblau, S. G. & You, Q. (2011). Eur. J. Med. Chem. 46, 3551-3563.]) and anti­tumor (Kaushik et al., 2012[Kaushik, N. K., Kim, H. S., Chae, Y. J., Lee, Y. N., Kwon, G., Choi, E. H. & Kim, I. T. (2012). Molecules, 17, 11456-11468.]). The quinoline ring system is one of the most commonly encountered heterocycles in medicinal chemistry (Bouraiou et al., 2007[Bouraiou, A., Belfaitah, A., Bouacida, S., Benard-Rocherulle, P. & Carboni, B. (2007). Acta Cryst. E63, o2133-o2135.]). Substituted quinolines possess diverse chemotherapeutic activities including anti­bacterial (Kidwai et al., 2000[Kidwai, M., Bhushan, K., Sapra, P., Saxena, R. & Gupta, R. (2000). Bioorg. Med. Chem. 8, 69-72.]), anti­fungal (Musiol et al., 2006[Musiol, R., Jampilek, J., Buchta, V., Silva, L., Niedbala, H., Podeszwa, B., Palka, A., Majerz-Maniecka, K., Oleksyn, B. & Polanski, J. (2006). Bioorg. Med. Chem. 14, 3592-3598.]), anti­malarial (Charris et al., 2005[Charris, J., Dominguez, J., Gamboa, N., Rodrigues, J. & Angel, J. (2005). Eur. J. Med. Chem. 40, 875-881.]; Cunico et al., 2006[Cunico, W., Cechinel, C., Bonacorso, H., Martins, M., Zanatta, N., de Souza, N., Freitas, I., Soares, R. & Krettli, A. (2006). Bioorg. Med. Chem. Lett. 16, 649-653.]) and anti­tumor (Chen et al., 2006[Chen, Y., Huang, C., Huang, Z., Tseng, C., Chang, F., Yang, S., Lin, S. & Tzeng, C. (2006). Bioorg. Med. Chem. 14, 3098-3105.]). As part of our studies in this area, we report herein the synthesis and crystal structure of the title compound.

In the asymmetric unit (Fig. 1[link]), the two independent mol­ecules A and B form a dimer via N—H⋯O hydrogen bonds (Table 1[link]). In both mol­ecules, the cyclo­hexene rings of the fused tetra­cyclic cores are puckered with QT = 0.438 (2) Å, θ = 65.0 (2)°, φ = 277.0 (3)° in A and QT = 0.481 (2) Å, θ = 111.8 (2) °, φ = 87.2 (2) ° in B. In both A and B, the mol­ecular conformation is stabilized by an N—H⋯O hydrogen bonds.

Table 1
Hydrogen-bond geometry (Å, °)

Cg8, Cg9 and Cg11 are the centroids of the O3B/C17B–C20B furan, N1B/C4B–C8B pyridine and C9B–C14B benzene rings, respectively.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
N2A—HN2A⋯O1A 0.83 (3) 2.23 (3) 2.839 (2) 131 (2)
N2A—HN2A⋯O1B 0.83 (3) 2.33 (3) 2.962 (2) 134 (2)
N2A—HN2B⋯O3A 0.86 (3) 2.17 (3) 2.869 (3) 138 (2)
N2B—HN2D⋯O1A 0.87 (3) 2.33 (2) 2.998 (2) 134 (2)
N2B—HN2D⋯O1B 0.87 (3) 2.17 (2) 2.802 (2) 129 (2)
N2B—HN2C⋯Cg8 0.83 (3) 2.55 (3) 3.294 (2) 150 (2)
C18B—H18B⋯Cg11i 0.93 2.53 3.353 (2) 148
C21A—H21A⋯Cg9i 0.97 2.96 3.718 (2) 136
C15A—H15A⋯N1Aii 0.97 2.61 3.386 (2) 137
Symmetry codes: (i) [x-{\script{3\over 2}}, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]; (ii) -x, -y+1, -z+2.
[Figure 1]
Figure 1
A view of mol­ecules A and B in the asymmetric unit of the title compound, with displacement ellipsoids drawn at the 50% probability level. For clarity, only the major disorder component of the furan ring in mol­ecule A is shown.

In the crystal, mol­ecular layers can be found in the (110) plane which are connected by C—H⋯π and C—H⋯N inter­actions (Fig. 2[link], Table 1[link]). There is a π–π inter­action between the N1A/C4A–C8A and C9A–C14A(−x, −y + 1, −z + 2) rings with a centroid–centroid distance of 3.7975 (10) Å.

[Figure 2]
Figure 2
Packing of the title mol­ecule, viewed down the a axis, with the hydrogen bonds shown by dotted lines. For clarity, the minor disorder component of the furan ring in mol­ecule A is omitted.

Synthesis and crystallization

To a mixture of 3-cyano-5,6-di­hydro-4-(2-fur­yl)-benzo[h]quinoline-2(1H)-thione (10 mmol) and ethyl chloro­acetate (10 mmol) in ethanol (20 ml) containing sodium ethoxide (20 mmol) was heated under reflux for one h and then allowed to cool. The solid that formed was collected and recrystallized from ethanol. Yield: 77%; m.p. 460–461 K. IR: 3490, 3360 (NH2), 1665 (C=O) cm-1. 1H NMR (CDCl3): 8.45 (m, 1H, CH–fur­yl); 6.60 (m, 2H, 2CH–fur­yl); 7.15–7.75 (m, 4H, ArH); 5.75 (s, 2H, NH2); 4.02–4.45 (q, 2H, OCH2); 2.85 (t, 4H, CH2—CH2); 1.30–1.45 (t, 3H, CH3 of ester) p.p.m.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. Atoms O3/C17–C20 atoms of the furan ring of mol­ecule A are disordered over two sets of sites with an occupancy ratio 0.735 (3):0.265 (3).

Table 2
Experimental details

Crystal data
Chemical formula C22H18N2O3S
Mr 390.44
Crystal system, space group Monoclinic, P21/n
Temperature (K) 173
a, b, c (Å) 11.5227 (1), 25.5293 (3), 12.4749 (1)
β (°) 90.038 (1)
V (Å3) 3669.70 (6)
Z 8
Radiation type Cu Kα
μ (mm−1) 1.79
Crystal size (mm) 0.24 × 0.22 × 0.18
 
Data collection
Diffractometer Rigaku Oxford Diffraction
Absorption correction Multi-scan (CrysAlis PRO; Agilent, 2014[Agilent (2014). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.])
Tmin, Tmax 0.850, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections 26340, 7070, 6264
Rint 0.041
(sin θ/λ)max (Å−1) 0.615
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.121, 1.02
No. of reflections 7070
No. of parameters 535
No. of restraints 6
H-atom treatment H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3) 0.51, −0.35
Computer programs: CrysAlis PRO (Agilent, 2014[Agilent (2014). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.]), SHELXT (Sheldrick, 2015a[Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.]), SHELXL2014 (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]) and OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]).

Structural data

CCDC reference: 1519100

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314616018848/zp4010sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314616018848/zp4010Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314616018848/zp4010Isup3.cml

checkCIF report


Computing details top

Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: 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); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Ethyl 8-amino-7-(furan-2-yl)-5,6-dihydrothieno[2,3-b]benzo[h]quinoline-9-carboxylate top
Crystal data top
C22H18N2O3SF(000) = 1632
Mr = 390.44Dx = 1.413 Mg m−3
Monoclinic, P21/nCu Kα radiation, λ = 1.54184 Å
a = 11.5227 (1) ÅCell parameters from 11878 reflections
b = 25.5293 (3) Åθ = 4.0–71.5°
c = 12.4749 (1) ŵ = 1.79 mm−1
β = 90.038 (1)°T = 173 K
V = 3669.70 (6) Å3Prism, yellow
Z = 80.24 × 0.22 × 0.18 mm
Data collection top
Rigaku Oxford Diffraction
diffractometer		7070 independent reflections
Radiation source: Enhance (Cu) X-ray Source6264 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
ω scansθmax = 71.6°, θmin = 3.5°
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2014)		h = −14→14
Tmin = 0.850, Tmax = 1.000k = −31→31
26340 measured reflectionsl = −15→9
Refinement top
Refinement on F26 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.042H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.121 w = 1/[σ2(Fo2) + (0.0748P)2 + 1.4658P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
7070 reflectionsΔρmax = 0.51 e Å−3
535 parametersΔρmin = −0.35 e Å−3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
S1A0.22490 (3)0.33984 (2)0.86042 (3)0.02556 (12)
O1A0.56095 (11)0.33865 (5)0.80644 (11)0.0341 (3)
O2A0.42720 (11)0.27591 (5)0.83821 (10)0.0303 (3)
N1A0.05971 (12)0.41276 (5)0.86245 (11)0.0241 (3)
N2A0.46257 (14)0.43728 (7)0.75339 (14)0.0341 (3)
HN2A0.522 (2)0.4191 (10)0.7475 (19)0.041*
HN2B0.462 (2)0.4705 (10)0.7422 (19)0.041*
C1A0.46067 (15)0.32571 (7)0.82123 (13)0.0257 (3)
C2A0.36303 (14)0.36142 (6)0.82271 (13)0.0254 (3)
C3A0.36690 (14)0.41373 (6)0.79308 (13)0.0245 (3)
C4A0.25402 (14)0.43856 (6)0.80529 (13)0.0231 (3)
C5A0.17046 (14)0.40254 (6)0.84125 (13)0.0232 (3)
C6A0.21524 (14)0.49043 (6)0.78678 (13)0.0241 (3)
C7A0.09879 (14)0.50196 (6)0.80572 (13)0.0241 (3)
C8A0.02490 (14)0.46196 (6)0.84584 (12)0.0236 (3)
C9A−0.09666 (14)0.47437 (7)0.87498 (13)0.0249 (3)
C10A−0.17635 (15)0.43420 (7)0.89447 (14)0.0293 (4)
H10A−0.1538630.3994750.8856790.035*
C11A−0.28851 (16)0.44565 (8)0.92675 (15)0.0338 (4)
H11A−0.3411930.4187520.9393540.041*
C12A−0.32185 (16)0.49745 (8)0.94017 (15)0.0354 (4)
H12A−0.3969790.5053150.9620870.042*
C13A−0.24327 (16)0.53752 (7)0.92095 (15)0.0324 (4)
H13A−0.2663260.5721190.9304110.039*
C14A−0.13053 (15)0.52677 (7)0.88773 (13)0.0268 (3)
C15A−0.04349 (16)0.56975 (7)0.86893 (15)0.0303 (4)
H15A−0.0038430.5775050.9356900.036*
H15B−0.0839230.6011830.8462700.036*
C16A0.04587 (15)0.55486 (6)0.78416 (14)0.0285 (3)
H16A0.0089020.5544930.7142800.034*
H16B0.1067690.5810820.7827480.034*
C17A0.2979 (7)0.5314 (4)0.7524 (8)0.0262 (10)0.735 (3)
C18A0.2961 (3)0.56622 (11)0.6707 (2)0.0369 (6)0.735 (3)
H18A0.2400170.5691800.6174130.044*0.735 (3)
C19A0.3992 (16)0.5979 (7)0.6830 (12)0.0446 (9)0.735 (3)
H19A0.4226710.6250510.6383840.054*0.735 (3)
C20A0.4539 (2)0.58110 (10)0.7692 (3)0.0417 (6)0.735 (3)
H20A0.5235150.5946830.7946910.050*0.735 (3)
O3A0.39379 (15)0.54085 (8)0.81596 (17)0.0337 (4)0.735 (3)
C17C0.282 (2)0.5346 (11)0.741 (2)0.0262 (10)0.265 (3)
C18C0.3788 (7)0.5585 (3)0.7729 (7)0.0369 (6)0.265 (3)
H18C0.4220780.5515250.8341680.044*0.265 (3)
C19C0.402 (4)0.598 (2)0.692 (3)0.0446 (9)0.265 (3)
H19C0.4629360.6215980.6917960.054*0.265 (3)
C20C0.3211 (7)0.5927 (3)0.6206 (7)0.0417 (6)0.265 (3)
H20C0.3151170.6141250.5605510.050*0.265 (3)
O3C0.2450 (5)0.5525 (2)0.6428 (4)0.0337 (4)0.265 (3)
C21A0.51885 (17)0.23712 (7)0.83563 (16)0.0348 (4)
H21A0.5702140.2415880.8965860.042*
H21B0.5640680.2406750.7704780.042*
C22A0.4620 (2)0.18439 (8)0.83956 (18)0.0457 (5)
H22A0.4174160.1790790.7754110.069*
H22B0.4116320.1826000.9007530.069*
H22C0.5203480.1577010.8450370.069*
S1B1.02424 (3)0.42431 (2)0.56674 (3)0.02733 (12)
O1B0.69672 (11)0.43020 (5)0.65658 (11)0.0366 (3)
O2B0.82546 (11)0.49130 (5)0.60154 (12)0.0372 (3)
O3B0.86546 (14)0.21442 (6)0.60904 (12)0.0471 (4)
N1B1.18642 (12)0.34871 (5)0.56442 (11)0.0246 (3)
N2B0.78963 (13)0.33034 (7)0.69322 (14)0.0326 (3)
HN2C0.798 (2)0.3007 (10)0.7195 (19)0.039*
HN2D0.730 (2)0.3500 (10)0.7069 (18)0.039*
C1B0.79366 (15)0.44204 (7)0.62714 (14)0.0292 (4)
C2B0.88844 (14)0.40521 (7)0.61652 (14)0.0267 (3)
C3B0.88368 (14)0.35349 (7)0.64893 (13)0.0251 (3)
C4B0.99295 (14)0.32699 (6)0.62983 (12)0.0238 (3)
C5B1.07690 (14)0.36130 (6)0.58800 (13)0.0245 (3)
C6B1.02569 (14)0.27431 (6)0.64358 (12)0.0236 (3)
C7B1.13874 (14)0.25994 (6)0.61924 (13)0.0251 (3)
C8B1.21695 (14)0.29883 (6)0.58245 (13)0.0243 (3)
C9B1.33937 (14)0.28466 (7)0.56314 (13)0.0253 (3)
C10B1.42585 (15)0.32303 (7)0.56302 (13)0.0276 (3)
H10B1.4062390.3579470.5741580.033*
C11B1.54065 (15)0.30924 (8)0.54638 (14)0.0316 (4)
H11B1.5980950.3348180.5477960.038*
C12B1.57021 (16)0.25741 (8)0.52763 (15)0.0361 (4)
H12B1.6472290.2483350.5153180.043*
C13B1.48511 (17)0.21918 (8)0.52722 (15)0.0352 (4)
H13B1.5053790.1845240.5139310.042*
C14B1.36936 (15)0.23194 (7)0.54647 (14)0.0290 (4)
C15B1.27430 (17)0.19147 (7)0.54764 (16)0.0348 (4)
H15C1.3073420.1573090.5627360.042*
H15D1.2377430.1899930.4776430.042*
C16B1.18314 (16)0.20466 (7)0.63247 (16)0.0331 (4)
H16C1.1188170.1803190.6265800.040*
H16D1.2169310.2007400.7032490.040*
C17B0.94080 (14)0.23500 (6)0.68132 (14)0.0252 (3)
C18B0.91781 (17)0.21757 (8)0.78011 (15)0.0365 (4)
H18B0.9563650.2264160.8430770.044*
C19B0.82130 (19)0.18236 (9)0.7690 (2)0.0507 (6)
H19B0.7856300.1634450.8234940.061*
C20B0.7931 (2)0.18204 (9)0.6666 (2)0.0536 (6)
H20B0.7326020.1626260.6372950.064*
C21B0.73855 (18)0.53200 (8)0.61779 (17)0.0404 (4)
H21C0.7768690.5656050.6257010.048*
H21D0.6960330.5249210.6832960.048*
C22B0.6554 (2)0.53445 (9)0.52547 (19)0.0481 (5)
H22D0.6973690.5412810.4605320.072*
H22E0.6002060.5620130.5375280.072*
H22F0.6152240.5016390.5192490.072*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S1A0.0241 (2)0.01813 (19)0.0345 (2)−0.00011 (14)0.00498 (15)0.00198 (14)
O1A0.0239 (6)0.0310 (6)0.0474 (7)0.0021 (5)0.0016 (5)−0.0010 (5)
O2A0.0304 (6)0.0227 (6)0.0377 (6)0.0045 (5)0.0024 (5)0.0018 (5)
N1A0.0226 (7)0.0211 (6)0.0286 (7)−0.0009 (5)0.0026 (5)−0.0010 (5)
N2A0.0227 (7)0.0253 (8)0.0543 (10)0.0005 (6)0.0072 (7)0.0045 (7)
C1A0.0276 (8)0.0244 (8)0.0252 (8)0.0026 (7)0.0009 (6)−0.0006 (6)
C2A0.0224 (8)0.0232 (8)0.0305 (8)−0.0006 (6)0.0032 (6)−0.0006 (6)
C3A0.0230 (8)0.0226 (8)0.0280 (8)−0.0010 (6)0.0013 (6)−0.0024 (6)
C4A0.0235 (8)0.0213 (7)0.0247 (7)−0.0018 (6)0.0028 (6)−0.0012 (6)
C5A0.0249 (8)0.0192 (7)0.0255 (7)−0.0010 (6)0.0014 (6)−0.0010 (6)
C6A0.0255 (8)0.0204 (7)0.0263 (8)−0.0012 (6)0.0031 (6)−0.0004 (6)
C7A0.0258 (8)0.0212 (8)0.0254 (8)0.0002 (6)0.0018 (6)0.0004 (6)
C8A0.0235 (8)0.0225 (8)0.0247 (7)−0.0009 (6)0.0008 (6)−0.0012 (6)
C9A0.0229 (8)0.0260 (8)0.0258 (8)0.0006 (6)−0.0002 (6)0.0001 (6)
C10A0.0258 (8)0.0291 (8)0.0329 (9)−0.0020 (7)0.0016 (7)−0.0011 (7)
C11A0.0254 (9)0.0390 (10)0.0370 (9)−0.0054 (7)0.0027 (7)0.0014 (8)
C12A0.0227 (8)0.0456 (11)0.0377 (9)0.0060 (7)0.0044 (7)0.0028 (8)
C13A0.0299 (9)0.0330 (9)0.0344 (9)0.0074 (7)0.0033 (7)0.0020 (7)
C14A0.0255 (8)0.0281 (8)0.0270 (8)0.0034 (6)0.0005 (6)0.0018 (6)
C15A0.0302 (9)0.0211 (8)0.0396 (9)0.0048 (7)0.0055 (7)0.0014 (7)
C16A0.0279 (8)0.0229 (8)0.0346 (9)0.0018 (6)0.0054 (7)0.0051 (7)
C17A0.024 (3)0.0190 (14)0.036 (2)0.0028 (19)0.0079 (15)0.0007 (10)
C18A0.0445 (16)0.0279 (12)0.0384 (13)−0.0023 (11)0.0120 (12)0.0092 (10)
C19A0.0494 (16)0.0260 (9)0.059 (3)−0.0094 (10)0.0248 (18)0.0026 (18)
C20A0.0374 (13)0.0255 (12)0.0622 (17)−0.0127 (10)0.0167 (12)−0.0029 (11)
O3A0.0283 (8)0.0282 (9)0.0444 (10)−0.0104 (7)0.0024 (7)0.0012 (8)
C17C0.024 (3)0.0190 (14)0.036 (2)0.0028 (19)0.0079 (15)0.0007 (10)
C18C0.0445 (16)0.0279 (12)0.0384 (13)−0.0023 (11)0.0120 (12)0.0092 (10)
C19C0.0494 (16)0.0260 (9)0.059 (3)−0.0094 (10)0.0248 (18)0.0026 (18)
C20C0.0374 (13)0.0255 (12)0.0622 (17)−0.0127 (10)0.0167 (12)−0.0029 (11)
O3C0.0283 (8)0.0282 (9)0.0444 (10)−0.0104 (7)0.0024 (7)0.0012 (8)
C21A0.0384 (10)0.0273 (9)0.0386 (10)0.0110 (7)−0.0054 (8)−0.0009 (7)
C22A0.0592 (13)0.0262 (9)0.0518 (12)0.0084 (9)−0.0151 (10)0.0008 (8)
S1B0.0224 (2)0.0226 (2)0.0370 (2)0.00243 (14)0.00525 (16)0.00390 (15)
O1B0.0248 (6)0.0362 (7)0.0488 (8)0.0053 (5)0.0069 (5)0.0077 (6)
O2B0.0293 (7)0.0292 (6)0.0531 (8)0.0070 (5)0.0080 (6)0.0060 (6)
O3B0.0457 (8)0.0517 (9)0.0440 (8)−0.0184 (7)−0.0076 (6)−0.0019 (7)
N1B0.0214 (7)0.0239 (7)0.0286 (7)0.0008 (5)0.0027 (5)0.0010 (5)
N2B0.0215 (7)0.0279 (8)0.0483 (9)0.0003 (6)0.0052 (6)0.0035 (7)
C1B0.0240 (8)0.0309 (9)0.0327 (9)0.0029 (7)0.0020 (7)0.0032 (7)
C2B0.0213 (8)0.0280 (8)0.0308 (8)0.0011 (6)0.0023 (6)0.0008 (6)
C3B0.0206 (8)0.0279 (8)0.0268 (8)−0.0003 (6)−0.0013 (6)−0.0024 (6)
C4B0.0219 (8)0.0255 (8)0.0241 (7)−0.0003 (6)−0.0009 (6)−0.0006 (6)
C5B0.0239 (8)0.0226 (8)0.0269 (8)0.0003 (6)−0.0007 (6)−0.0002 (6)
C6B0.0234 (8)0.0235 (8)0.0240 (7)−0.0027 (6)−0.0027 (6)−0.0011 (6)
C7B0.0261 (8)0.0230 (8)0.0261 (8)0.0009 (6)−0.0019 (6)0.0006 (6)
C8B0.0239 (8)0.0244 (8)0.0247 (7)0.0014 (6)−0.0002 (6)−0.0016 (6)
C9B0.0250 (8)0.0282 (8)0.0229 (7)0.0044 (6)0.0006 (6)0.0020 (6)
C10B0.0268 (8)0.0309 (8)0.0252 (8)0.0030 (7)−0.0010 (6)0.0000 (6)
C11B0.0238 (8)0.0413 (10)0.0297 (8)0.0004 (7)−0.0016 (6)0.0025 (7)
C12B0.0240 (8)0.0473 (11)0.0371 (9)0.0101 (8)0.0019 (7)0.0048 (8)
C13B0.0331 (10)0.0333 (9)0.0393 (10)0.0120 (7)0.0030 (7)0.0035 (8)
C14B0.0284 (9)0.0284 (8)0.0303 (8)0.0063 (7)0.0011 (7)0.0026 (7)
C15B0.0348 (9)0.0230 (8)0.0465 (10)0.0052 (7)0.0023 (8)−0.0011 (7)
C16B0.0299 (9)0.0253 (9)0.0443 (10)0.0020 (7)0.0039 (7)0.0052 (7)
C17B0.0209 (7)0.0227 (8)0.0320 (8)0.0007 (6)−0.0025 (6)−0.0002 (6)
C18B0.0353 (10)0.0482 (11)0.0260 (8)−0.0003 (8)0.0001 (7)0.0041 (8)
C19B0.0383 (11)0.0389 (11)0.0747 (16)0.0060 (9)0.0215 (11)0.0276 (11)
C20B0.0379 (11)0.0360 (11)0.0869 (18)−0.0159 (9)0.0030 (11)−0.0056 (11)
C21B0.0388 (10)0.0339 (10)0.0485 (11)0.0075 (8)0.0056 (9)−0.0004 (8)
C22B0.0459 (12)0.0428 (12)0.0555 (13)0.0132 (9)0.0012 (10)0.0059 (10)
Geometric parameters (Å, º) top
S1A—C5A1.7355 (16)C21A—H21B0.9700
S1A—C2A1.7489 (17)C22A—H22A0.9600
O1A—C1A1.216 (2)C22A—H22B0.9600
O2A—C1A1.345 (2)C22A—H22C0.9600
O2A—C21A1.448 (2)S1B—C5B1.7395 (16)
N1A—C5A1.329 (2)S1B—C2B1.7530 (17)
N1A—C8A1.335 (2)O1B—C1B1.214 (2)
N2A—C3A1.350 (2)O2B—C1B1.348 (2)
N2A—HN2A0.83 (3)O2B—C21B1.457 (2)
N2A—HN2B0.86 (3)O3B—C17B1.357 (2)
C1A—C2A1.448 (2)O3B—C20B1.377 (3)
C2A—C3A1.386 (2)N1B—C5B1.335 (2)
C3A—C4A1.455 (2)N1B—C8B1.340 (2)
C4A—C5A1.405 (2)N2B—C3B1.353 (2)
C4A—C6A1.416 (2)N2B—HN2C0.83 (3)
C6A—C7A1.394 (2)N2B—HN2D0.87 (3)
C6A—C17A1.479 (5)C1B—C2B1.447 (2)
C6A—C17C1.480 (12)C2B—C3B1.382 (2)
C7A—C8A1.421 (2)C3B—C4B1.449 (2)
C7A—C16A1.506 (2)C4B—C5B1.406 (2)
C8A—C9A1.482 (2)C4B—C6B1.407 (2)
C9A—C10A1.398 (2)C6B—C7B1.387 (2)
C9A—C14A1.403 (2)C6B—C17B1.479 (2)
C10A—C11A1.385 (3)C7B—C8B1.418 (2)
C10A—H10A0.9300C7B—C16B1.510 (2)
C11A—C12A1.387 (3)C8B—C9B1.476 (2)
C11A—H11A0.9300C9B—C10B1.397 (2)
C12A—C13A1.387 (3)C9B—C14B1.405 (2)
C12A—H12A0.9300C10B—C11B1.385 (2)
C13A—C14A1.391 (2)C10B—H10B0.9300
C13A—H13A0.9300C11B—C12B1.386 (3)
C14A—C15A1.505 (2)C11B—H11B0.9300
C15A—C16A1.525 (2)C12B—C13B1.384 (3)
C15A—H15A0.9700C12B—H12B0.9300
C15A—H15B0.9700C13B—C14B1.394 (3)
C16A—H16A0.9700C13B—H13B0.9300
C16A—H16B0.9700C14B—C15B1.506 (3)
C17A—C18A1.352 (6)C15B—C16B1.529 (3)
C17A—O3A1.381 (6)C15B—H15C0.9700
C18A—C19A1.445 (9)C15B—H15D0.9700
C18A—H18A0.9300C16B—H16C0.9700
C19A—C20A1.317 (12)C16B—H16D0.9700
C19A—H19A0.9300C17B—C18B1.337 (3)
C20A—O3A1.370 (3)C18B—C19B1.437 (3)
C20A—H20A0.9300C18B—H18B0.9300
C17C—C18C1.335 (17)C19B—C20B1.318 (4)
C17C—O3C1.37 (2)C19B—H19B0.9300
C18C—C19C1.442 (19)C20B—H20B0.9300
C18C—H18C0.9300C21B—C22B1.499 (3)
C19C—C20C1.30 (3)C21B—H21C0.9700
C19C—H19C0.9300C21B—H21D0.9700
C20C—O3C1.379 (8)C22B—H22D0.9600
C20C—H20C0.9300C22B—H22E0.9600
C21A—C22A1.498 (3)C22B—H22F0.9600
C21A—H21A0.9700
C5A—S1A—C2A90.08 (8)H21A—C21A—H21B108.5
C1A—O2A—C21A115.70 (14)C21A—C22A—H22A109.5
C5A—N1A—C8A116.25 (14)C21A—C22A—H22B109.5
C3A—N2A—HN2A117.3 (17)H22A—C22A—H22B109.5
C3A—N2A—HN2B119.9 (16)C21A—C22A—H22C109.5
HN2A—N2A—HN2B122 (2)H22A—C22A—H22C109.5
O1A—C1A—O2A123.58 (15)H22B—C22A—H22C109.5
O1A—C1A—C2A124.71 (16)C5B—S1B—C2B90.01 (8)
O2A—C1A—C2A111.72 (14)C1B—O2B—C21B116.43 (15)
C3A—C2A—C1A125.29 (15)C17B—O3B—C20B105.86 (17)
C3A—C2A—S1A113.86 (12)C5B—N1B—C8B116.09 (14)
C1A—C2A—S1A120.82 (13)C3B—N2B—HN2C118.1 (17)
N2A—C3A—C2A123.59 (16)C3B—N2B—HN2D117.4 (16)
N2A—C3A—C4A125.07 (15)HN2C—N2B—HN2D123 (2)
C2A—C3A—C4A111.28 (14)O1B—C1B—O2B123.64 (16)
C5A—C4A—C6A116.60 (15)O1B—C1B—C2B124.09 (17)
C5A—C4A—C3A111.16 (14)O2B—C1B—C2B112.27 (14)
C6A—C4A—C3A132.24 (15)C3B—C2B—C1B124.31 (15)
N1A—C5A—C4A126.37 (15)C3B—C2B—S1B113.89 (12)
N1A—C5A—S1A120.04 (12)C1B—C2B—S1B121.71 (13)
C4A—C5A—S1A113.57 (12)N2B—C3B—C2B124.67 (16)
C7A—C6A—C4A118.25 (15)N2B—C3B—C4B124.03 (16)
C7A—C6A—C17A121.3 (4)C2B—C3B—C4B111.30 (14)
C4A—C6A—C17A120.4 (4)C5B—C4B—C6B117.14 (15)
C7A—C6A—C17C113.9 (14)C5B—C4B—C3B111.62 (14)
C4A—C6A—C17C127.7 (15)C6B—C4B—C3B131.22 (15)
C6A—C7A—C8A119.02 (15)N1B—C5B—C4B125.63 (15)
C6A—C7A—C16A123.28 (15)N1B—C5B—S1B121.24 (12)
C8A—C7A—C16A117.69 (14)C4B—C5B—S1B113.13 (12)
N1A—C8A—C7A123.43 (15)C7B—C6B—C4B118.55 (15)
N1A—C8A—C9A116.55 (14)C7B—C6B—C17B120.77 (15)
C7A—C8A—C9A119.99 (14)C4B—C6B—C17B120.67 (15)
C10A—C9A—C14A119.81 (15)C6B—C7B—C8B118.87 (15)
C10A—C9A—C8A120.47 (15)C6B—C7B—C16B122.78 (15)
C14A—C9A—C8A119.66 (15)C8B—C7B—C16B118.33 (15)
C11A—C10A—C9A120.58 (17)N1B—C8B—C7B123.58 (15)
C11A—C10A—H10A119.7N1B—C8B—C9B117.15 (14)
C9A—C10A—H10A119.7C7B—C8B—C9B119.27 (15)
C10A—C11A—C12A119.66 (17)C10B—C9B—C14B119.73 (16)
C10A—C11A—H11A120.2C10B—C9B—C8B120.65 (15)
C12A—C11A—H11A120.2C14B—C9B—C8B119.61 (15)
C13A—C12A—C11A120.09 (17)C11B—C10B—C9B120.21 (17)
C13A—C12A—H12A120.0C11B—C10B—H10B119.9
C11A—C12A—H12A120.0C9B—C10B—H10B119.9
C12A—C13A—C14A121.05 (17)C10B—C11B—C12B120.20 (17)
C12A—C13A—H13A119.5C10B—C11B—H11B119.9
C14A—C13A—H13A119.5C12B—C11B—H11B119.9
C13A—C14A—C9A118.81 (16)C13B—C12B—C11B119.98 (17)
C13A—C14A—C15A121.67 (16)C13B—C12B—H12B120.0
C9A—C14A—C15A119.48 (15)C11B—C12B—H12B120.0
C14A—C15A—C16A112.13 (14)C12B—C13B—C14B120.85 (17)
C14A—C15A—H15A109.2C12B—C13B—H13B119.6
C16A—C15A—H15A109.2C14B—C13B—H13B119.6
C14A—C15A—H15B109.2C13B—C14B—C9B119.00 (17)
C16A—C15A—H15B109.2C13B—C14B—C15B122.50 (16)
H15A—C15A—H15B107.9C9B—C14B—C15B118.48 (15)
C7A—C16A—C15A111.91 (14)C14B—C15B—C16B110.83 (15)
C7A—C16A—H16A109.2C14B—C15B—H15C109.5
C15A—C16A—H16A109.2C16B—C15B—H15C109.5
C7A—C16A—H16B109.2C14B—C15B—H15D109.5
C15A—C16A—H16B109.2C16B—C15B—H15D109.5
H16A—C16A—H16B107.9H15C—C15B—H15D108.1
C18A—C17A—O3A109.3 (3)C7B—C16B—C15B111.29 (15)
C18A—C17A—C6A132.4 (5)C7B—C16B—H16C109.4
O3A—C17A—C6A118.1 (4)C15B—C16B—H16C109.4
C17A—C18A—C19A106.0 (5)C7B—C16B—H16D109.4
C17A—C18A—H18A127.0C15B—C16B—H16D109.4
C19A—C18A—H18A127.0H16C—C16B—H16D108.0
C20A—C19A—C18A107.3 (5)C18B—C17B—O3B110.89 (16)
C20A—C19A—H19A126.3C18B—C17B—C6B130.61 (16)
C18A—C19A—H19A126.3O3B—C17B—C6B118.31 (15)
C19A—C20A—O3A110.5 (4)C17B—C18B—C19B105.84 (18)
C19A—C20A—H20A124.8C17B—C18B—H18B127.1
O3A—C20A—H20A124.8C19B—C18B—H18B127.1
C20A—O3A—C17A106.9 (3)C20B—C19B—C18B106.74 (18)
C18C—C17C—O3C111.9 (10)C20B—C19B—H19B126.6
C18C—C17C—C6A131.8 (15)C18B—C19B—H19B126.6
O3C—C17C—C6A116.1 (13)C19B—C20B—O3B110.66 (19)
C17C—C18C—C19C105.3 (15)C19B—C20B—H20B124.7
C17C—C18C—H18C127.3O3B—C20B—H20B124.7
C19C—C18C—H18C127.3O2B—C21B—C22B111.23 (17)
C20C—C19C—C18C106.2 (16)O2B—C21B—H21C109.4
C20C—C19C—H19C126.9C22B—C21B—H21C109.4
C18C—C19C—H19C126.9O2B—C21B—H21D109.4
C19C—C20C—O3C113.0 (11)C22B—C21B—H21D109.4
C19C—C20C—H20C123.5H21C—C21B—H21D108.0
O3C—C20C—H20C123.5C21B—C22B—H22D109.5
C17C—O3C—C20C103.3 (8)C21B—C22B—H22E109.5
O2A—C21A—C22A107.13 (16)H22D—C22B—H22E109.5
O2A—C21A—H21A110.3C21B—C22B—H22F109.5
C22A—C21A—H21A110.3H22D—C22B—H22F109.5
O2A—C21A—H21B110.3H22E—C22B—H22F109.5
C22A—C21A—H21B110.3
C21A—O2A—C1A—O1A−1.3 (2)C6A—C17C—C18C—C19C178 (5)
C21A—O2A—C1A—C2A178.60 (14)C17C—C18C—C19C—C20C−1 (6)
O1A—C1A—C2A—C3A9.5 (3)C18C—C19C—C20C—O3C−2 (6)
O2A—C1A—C2A—C3A−170.43 (15)C18C—C17C—O3C—C20C−5 (3)
O1A—C1A—C2A—S1A−172.33 (14)C6A—C17C—O3C—C20C180 (2)
O2A—C1A—C2A—S1A7.7 (2)C19C—C20C—O3C—C17C4 (4)
C5A—S1A—C2A—C3A−2.08 (13)C1A—O2A—C21A—C22A−171.67 (15)
C5A—S1A—C2A—C1A179.55 (14)C21B—O2B—C1B—O1B4.1 (3)
C1A—C2A—C3A—N2A3.6 (3)C21B—O2B—C1B—C2B−175.31 (16)
S1A—C2A—C3A—N2A−174.69 (14)O1B—C1B—C2B—C3B−7.0 (3)
C1A—C2A—C3A—C4A−179.28 (15)O2B—C1B—C2B—C3B172.40 (16)
S1A—C2A—C3A—C4A2.43 (18)O1B—C1B—C2B—S1B176.55 (15)
N2A—C3A—C4A—C5A175.54 (16)O2B—C1B—C2B—S1B−4.0 (2)
C2A—C3A—C4A—C5A−1.5 (2)C5B—S1B—C2B—C3B0.65 (14)
N2A—C3A—C4A—C6A−3.6 (3)C5B—S1B—C2B—C1B177.45 (15)
C2A—C3A—C4A—C6A179.29 (17)C1B—C2B—C3B—N2B1.0 (3)
C8A—N1A—C5A—C4A1.3 (2)S1B—C2B—C3B—N2B177.72 (14)
C8A—N1A—C5A—S1A179.82 (12)C1B—C2B—C3B—C4B−178.74 (16)
C6A—C4A—C5A—N1A−2.1 (2)S1B—C2B—C3B—C4B−2.04 (18)
C3A—C4A—C5A—N1A178.59 (15)N2B—C3B—C4B—C5B−177.03 (16)
C6A—C4A—C5A—S1A179.31 (12)C2B—C3B—C4B—C5B2.7 (2)
C3A—C4A—C5A—S1A−0.02 (18)N2B—C3B—C4B—C6B4.7 (3)
C2A—S1A—C5A—N1A−177.56 (14)C2B—C3B—C4B—C6B−175.54 (16)
C2A—S1A—C5A—C4A1.15 (13)C8B—N1B—C5B—C4B0.3 (2)
C5A—C4A—C6A—C7A0.3 (2)C8B—N1B—C5B—S1B−178.94 (12)
C3A—C4A—C6A—C7A179.43 (16)C6B—C4B—C5B—N1B−3.0 (2)
C5A—C4A—C6A—C17A177.9 (5)C3B—C4B—C5B—N1B178.47 (15)
C3A—C4A—C6A—C17A−2.9 (5)C6B—C4B—C5B—S1B176.26 (11)
C5A—C4A—C6A—C17C−174.5 (14)C3B—C4B—C5B—S1B−2.28 (18)
C3A—C4A—C6A—C17C4.6 (14)C2B—S1B—C5B—N1B−179.74 (14)
C4A—C6A—C7A—C8A2.0 (2)C2B—S1B—C5B—C4B0.97 (13)
C17A—C6A—C7A—C8A−175.6 (5)C5B—C4B—C6B—C7B2.4 (2)
C17C—C6A—C7A—C8A177.5 (13)C3B—C4B—C6B—C7B−179.40 (16)
C4A—C6A—C7A—C16A−177.02 (15)C5B—C4B—C6B—C17B−176.52 (14)
C17A—C6A—C7A—C16A5.4 (5)C3B—C4B—C6B—C17B1.7 (3)
C17C—C6A—C7A—C16A−1.5 (13)C4B—C6B—C7B—C8B0.5 (2)
C5A—N1A—C8A—C7A1.3 (2)C17B—C6B—C7B—C8B179.46 (14)
C5A—N1A—C8A—C9A−176.71 (14)C4B—C6B—C7B—C16B179.20 (15)
C6A—C7A—C8A—N1A−2.9 (2)C17B—C6B—C7B—C16B−1.9 (2)
C16A—C7A—C8A—N1A176.12 (15)C5B—N1B—C8B—C7B3.1 (2)
C6A—C7A—C8A—C9A174.99 (15)C5B—N1B—C8B—C9B−176.47 (14)
C16A—C7A—C8A—C9A−5.9 (2)C6B—C7B—C8B—N1B−3.5 (2)
N1A—C8A—C9A—C10A−14.4 (2)C16B—C7B—C8B—N1B177.76 (15)
C7A—C8A—C9A—C10A167.52 (15)C6B—C7B—C8B—C9B176.01 (14)
N1A—C8A—C9A—C14A162.75 (15)C16B—C7B—C8B—C9B−2.7 (2)
C7A—C8A—C9A—C14A−15.3 (2)N1B—C8B—C9B—C10B21.6 (2)
C14A—C9A—C10A—C11A−0.3 (3)C7B—C8B—C9B—C10B−157.97 (15)
C8A—C9A—C10A—C11A176.87 (16)N1B—C8B—C9B—C14B−159.47 (15)
C9A—C10A—C11A—C12A−0.2 (3)C7B—C8B—C9B—C14B21.0 (2)
C10A—C11A—C12A—C13A0.2 (3)C14B—C9B—C10B—C11B0.1 (2)
C11A—C12A—C13A—C14A0.2 (3)C8B—C9B—C10B—C11B179.05 (15)
C12A—C13A—C14A—C9A−0.7 (3)C9B—C10B—C11B—C12B1.3 (3)
C12A—C13A—C14A—C15A−178.61 (17)C10B—C11B—C12B—C13B−1.0 (3)
C10A—C9A—C14A—C13A0.7 (2)C11B—C12B—C13B—C14B−0.6 (3)
C8A—C9A—C14A—C13A−176.44 (15)C12B—C13B—C14B—C9B2.0 (3)
C10A—C9A—C14A—C15A178.67 (16)C12B—C13B—C14B—C15B−179.48 (18)
C8A—C9A—C14A—C15A1.5 (2)C10B—C9B—C14B—C13B−1.7 (2)
C13A—C14A—C15A—C16A−150.95 (16)C8B—C9B—C14B—C13B179.34 (15)
C9A—C14A—C15A—C16A31.2 (2)C10B—C9B—C14B—C15B179.67 (15)
C6A—C7A—C16A—C15A−142.57 (17)C8B—C9B—C14B—C15B0.7 (2)
C8A—C7A—C16A—C15A38.4 (2)C13B—C14B—C15B—C16B143.97 (17)
C14A—C15A—C16A—C7A−50.0 (2)C9B—C14B—C15B—C16B−37.5 (2)
C7A—C6A—C17A—C18A−53.5 (15)C6B—C7B—C16B—C15B147.24 (16)
C4A—C6A—C17A—C18A128.9 (11)C8B—C7B—C16B—C15B−34.1 (2)
C7A—C6A—C17A—O3A121.3 (7)C14B—C15B—C16B—C7B52.9 (2)
C4A—C6A—C17A—O3A−56.3 (12)C20B—O3B—C17B—C18B−0.7 (2)
O3A—C17A—C18A—C19A1.8 (15)C20B—O3B—C17B—C6B−176.30 (17)
C6A—C17A—C18A—C19A177.0 (16)C7B—C6B—C17B—C18B87.1 (2)
C17A—C18A—C19A—C20A−1 (2)C4B—C6B—C17B—C18B−94.0 (2)
C18A—C19A—C20A—O3A−0.7 (19)C7B—C6B—C17B—O3B−98.35 (19)
C19A—C20A—O3A—C17A1.8 (14)C4B—C6B—C17B—O3B80.6 (2)
C18A—C17A—O3A—C20A−2.3 (10)O3B—C17B—C18B—C19B1.1 (2)
C6A—C17A—O3A—C20A−178.2 (7)C6B—C17B—C18B—C19B175.93 (18)
C7A—C6A—C17C—C18C125 (4)C17B—C18B—C19B—C20B−1.0 (2)
C4A—C6A—C17C—C18C−60 (5)C18B—C19B—C20B—O3B0.6 (3)
C7A—C6A—C17C—O3C−61 (3)C17B—O3B—C20B—C19B0.1 (3)
C4A—C6A—C17C—O3C114 (2)C1B—O2B—C21B—C22B−82.2 (2)
O3C—C17C—C18C—C19C4 (4)
Hydrogen-bond geometry (Å, º) top
Cg8, Cg9 and Cg11 are the centroids of the O3B/C17B–C20B furan, N1B/C4B–C8B pyridine and C9B–C14B benzene rings, respectively.
D—H···AD—HH···AD···AD—H···A
N2A—HN2A···O1A0.83 (3)2.23 (3)2.839 (2)131 (2)
N2A—HN2A···O1B0.83 (3)2.33 (3)2.962 (2)134 (2)
N2A—HN2B···O3A0.86 (3)2.17 (3)2.869 (3)138 (2)
N2B—HN2D···O1A0.87 (3)2.33 (2)2.998 (2)134 (2)
N2B—HN2D···O1B0.87 (3)2.17 (2)2.802 (2)129 (2)
N2B—HN2C···Cg80.83 (3)2.55 (3)3.294 (2)150 (2)
C18B—H18B···Cg11i0.932.533.353 (2)148
C21A—H21A···Cg9i0.972.963.718 (2)136
C15A—H15A···N1Aii0.972.613.386 (2)137
Symmetry codes: (i) x−3/2, −y−1/2, z−1/2; (ii) −x, −y+1, −z+2.
 

Acknowledgements

JPJ would like to acknowledge the NSF–MRI program (grant No. CHE-1039027) for funds to purchase the X ray diffractometer.

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ISSN: 2414-3146
Volume 1| Part 11| November 2016| x161884
https://doi.org/10.1107/S2414314616018848
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