organic compounds
RS,4SR,4aRS,11aRS,11bSR)-5-oxo-3,4,4a,5,7,8,9,10,11,11a-decahydro-3,11b-epoxyazepino[2,1-a]isoindole-4-carboxylate
of methyl (3aDepartment of Chemistry, University of Douala, Faculty of Sciences, PO Box 24157, Douala, Republic of Cameroon, bDepartment of Organic Chemistry, Peoples' Friendship University of Russia, 6 Miklukho-Maklay St, Moscow 117198, Russian Federation, cDepartment of Chemistry & Biology, New Mexico Highlands University, 803 University Ave, Las Vegas, NM 87701, USA, and dDepartment of Inorganic Chemistry, Peoples' Friendship University of Russia, 6 Miklukho-Maklay St, Moscow 117198, Russian Federation
*Correspondence e-mail: flavien@mail.ru, vkh@xray.ineos.ac.ru
The title compound, C15H19NO4, is the a product of the esterification of the corresponding carbonic acid with methanol. The molecule comprises a fused tetracyclic system containing three five-membered rings (2-pyrrolidinone, tetrahydrofuran and dihydrofuran) and one seven-membered ring (azepane). The five-membered rings have the usual envelope conformations, with the quaternary C atom being the flap atom for the 2-pyrrolidinone ring, and the ether O atom being the common flap atom for the remaining rings. The seven-membered azepane ring adopts a chair conformation with the methine and middle methylene C atoms lying above and below the mean plane defined by the remaining five atoms. The carboxylate substituent is rotated by 77.56 (5)° with respect to the base plane of the tetrahydrofuran ring. In the crystal, the molecules are bound by weak C—H⋯O hydrogen-bonding interactions into puckered layers parallel to (001).
Keywords: crystal structure; 3,6a-epoxyisoindoles; azepane; intramolecular cycloaddition; C—H⋯O hydrogen bonds.
CCDC reference: 1422681
1. Related literature
For the synthesis of 2-(furan-2-yl)azepane, see: Asher et al. (1981); Shono et al. (1981); Nikolic & Beak (1997). For intramolecular cycloaddition reactions of α,β-unsaturated acid to α-furylamines (IMDAF reactions), see: Vogel et al. (1999); Zubkov et al. (2005). For related compounds, see: Zylber et al. (1995); Evans et al. (1999); Kachkovskyi & Kolodiazhnyi (2007); Kharitonov et al. (2009); Aabid et al. (2010); Zubkov et al. (2010, 2011, 2014); Toze et al. (2011); Wang & Li (2012); Zaytsev, Mikhailova et al. (2012); Zaytsev, Zubkov et al. 2012); Zaytsev et al. (2013); Chen et al. (2013); Hizartzidis et al. (2014).
2. Experimental
2.1. Crystal data
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2.3. Refinement
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Data collection: APEX2 (Bruker, 2005); cell SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supporting information
CCDC reference: 1422681
10.1107/S2056989015016679/tk5384sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2056989015016679/tk5384Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989015016679/tk5384Isup3.cml
In the last decade our synthetic group has published some effective strategies for the synthesis of 3,6a-epoxyisoindoles annulated with various heterocycles (Zubkov et al. 2010, 2011, 2014; Zaytsev, Mikhailova et al. 2012; Zaytsev, Zubkov et al. 2012; Zaytsev et al. 2013). These strategies were based on the intramolecular cycloaddition reaction of α,β-unsaturated acid to the heterocycles containing an α-furfurylamine fragment (IMDAF reaction) (Vogel et al., 1999; Zubkov et al., 2005). Therefore, within the scope of this investigation, the initial carboxylic acid was easily synthesized by the treatment of 2-(2-furyl)perhydroazepine (Asher et al., 1981; Shono et al., 1981; Nikolic et al., 1997) with maleic anhydride.
This work reports the structural characterization of 3,6a-epoxyisoindole annulated with perhydroazepine ring. The esterification of the initial carboxylic acid obtained as fine-crystalline powder is due to its poor solubility in most common organic solvents (Fig. 1).
The molecule of the title compound, C15H19NO4, (I) comprises a fused tetracyclic system containing three five-membered rings (2-pyrrolidinone, tetrahydrofuran and dihydrofuran) and one seven-membered ring (1,4-diazepine) (Fig. 2). The 2-pyrrolidinone, tetrahydrofuran and dihydrofuran five-membered rings have the usual envelope conformations (Zylber et al., 1995; Evans et al., 1999; Kachkovskyi et al., 2007; Kharitonov et al., 2009; Aabid et al., 2010; Toze et al., 2011; Wang et al., 2012; Chen et al., 2013; Hizartzidis et al., 2014). The seven-membered diazepine ring adopts a chair conformation. The nitrogen N6 atom has the slightly pyramidalized geometry (sum of the bond angles is 359.7 (4)°). The dihedral angle between the basal plane of the diazepine ring (C8—C9/C11—C11A) and the base plane of the pyrrolidinone ring (C4—C5—N6—C11A) is 66.55 (9)°). The carboxylate substituent is rotated by 77.56 (5)° to the base plane of the tetrahydrofuran ring.
The molecule of (I) possesses five asymmetric centers at the C3, C4, C4A, C11A and C11B carbon atoms and can have potentially numerous
The crystal of (I) is racemic and consists of enantiomeric pairs with the following of the centers: rac-3R*,4S*,4AR*,11AR*,11BS*.In the crystal, the molecules of (I) are bound by the weak intermolecular C—H···O hydrogen bonding interactions into puckered layers parallel to (001) (Fig. 3, Table 1).
A solution of the initial acid – (3R*,4S*,4aR*,11aR*,11bS*)-5-oxo-3,4,4a,5,7,8,9,10,11,11a-decahydro-3,11b-epoxyazepino[2,1-a]isoindole-4-carboxylic acid (0.5 g, 1.8 mmol) in methanol (30 mL) was refluxed for 3 h in the presence of catalytic amount of concentrated H2SO4 (monitoring by TLC until disappearance of the starting compound (eluent – EtOAc:hexane (1:3), Sorbfil). Then the solvent was evaporated. The residual oil was passed through a thin layer of aluminum oxide (eluent – chloroform). Chloroform was removed under reduced pressure. The crude ester was recrystallized from a mixture of EtOAc-EtOH to give the target compound I as white crystals. Yield is 0.31 g (58%). Single-crystals were isolated as fine needles by slow re-crystallization from EtOAc-EtOH. M.pt = 388–389 K. IR (KBr), ν/cm-1: 1741 (C=O), 1693 (C=O). EI–MS (70 eV), m/z (Ir(%)): 230 (5), 189 (52), 146 (96), 118 (19), 96 (100), 91 (17), 77 (18), 70 (17), 44 (33), 42 (25), 41 (18). 1H NMR (CDCl3, 400 MHz, 300 K): δ = 1.64–1.25 (m, 3H, H9B, H10A, H10B), 2.00–1.92 (m, 4H, H11B, H8A, H8B, H9A), 2.25–2.22 (m, 1H, H11A), 2.71 (d, 1H, H4, J4,4a = 9.0), 2.86 (d, 1H, H4a, J4a,4 = 9.0), 3.18–3.14 (m, 1H, H7B), 3.78–3.73 (m, 1H, H11A), 3.79 (s, 3H, CO2Me), 3.96 (m, 1H, H7A), 5.15 (d, 1H, H3, J3,2 = 1.7), 6.47 (dd, 1H, H2, J2,1 = 6.5, J2,3 = 1.7), 6.53 (d, 1H, H1, J1,2 = 6.5). 13C NMR (CDCl3, 100 MHz, 300 K): δ = 26.6, 27.6, 29.2, 33.6 (C8, C9, C10, C11), 43.5, 45.4, 49.6, 52.1 (C7, C4A, C13, C4), 59.6 (C11A), 81.2 (C3), 92.1 (C11B), 135.2, 137.4 (C1, C2), 170.5, 172.5 (CO2Me, NCO).
Data collection: APEX2 (Bruker, 2005); cell
SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).Fig. 1. Esterification of 5-oxo-3,4,4a,5,7,8,9,10,11,11a-decahydro-3,11b-epoxyazepino[2,1-a]isoindole-4-carboxylic acid with methanol. | |
Fig. 2. Molecular structure of (I). Displacement ellipsoids are shown at the 50% probability level. H atoms are presented as small spheres of arbitrary radius. | |
Fig. 3. Crystal packing of (I) along the a axis demonstrating the H-bonded puckered layers parallel to (001). Dashed lines indicate the weak intermolecular C—H···O hydrogen-bonding interactions. |
C15H19NO4 | Z = 2 |
Mr = 277.31 | F(000) = 296 |
Triclinic, P1 | Dx = 1.332 Mg m−3 |
a = 7.5460 (8) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.6984 (10) Å | Cell parameters from 4971 reflections |
c = 10.2894 (10) Å | θ = 2.3–29.5° |
α = 103.857 (2)° | µ = 0.10 mm−1 |
β = 94.745 (2)° | T = 290 K |
γ = 106.620 (2)° | Prism, colourless |
V = 691.24 (12) Å3 | 0.30 × 0.25 × 0.25 mm |
Bruker APEXII CCD diffractometer | 2613 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.018 |
φ and ω scans | θmax = 28.0°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2003) | h = −9→9 |
Tmin = 0.959, Tmax = 0.969 | k = −12→12 |
9699 measured reflections | l = −13→13 |
3268 independent reflections |
Refinement on F2 | Primary atom site location: difference Fourier map |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.141 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0765P)2 + 0.153P] where P = (Fo2 + 2Fc2)/3 |
3268 reflections | (Δ/σ)max < 0.001 |
182 parameters | Δρmax = 0.37 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
C15H19NO4 | γ = 106.620 (2)° |
Mr = 277.31 | V = 691.24 (12) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.5460 (8) Å | Mo Kα radiation |
b = 9.6984 (10) Å | µ = 0.10 mm−1 |
c = 10.2894 (10) Å | T = 290 K |
α = 103.857 (2)° | 0.30 × 0.25 × 0.25 mm |
β = 94.745 (2)° |
Bruker APEXII CCD diffractometer | 3268 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2003) | 2613 reflections with I > 2σ(I) |
Tmin = 0.959, Tmax = 0.969 | Rint = 0.018 |
9699 measured reflections |
R[F2 > 2σ(F2)] = 0.048 | 0 restraints |
wR(F2) = 0.141 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.37 e Å−3 |
3268 reflections | Δρmin = −0.24 e Å−3 |
182 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.55178 (19) | 0.17386 (17) | 0.75675 (18) | 0.0471 (4) | |
H1 | 0.4515 | 0.2009 | 0.7244 | 0.056* | |
C2 | 0.5710 (2) | 0.12672 (19) | 0.86511 (18) | 0.0491 (4) | |
H2 | 0.4866 | 0.1136 | 0.9255 | 0.059* | |
C3 | 0.7587 (2) | 0.09790 (16) | 0.87191 (15) | 0.0403 (3) | |
H3 | 0.7723 | 0.0281 | 0.9240 | 0.048* | |
C4 | 0.91211 (19) | 0.25575 (15) | 0.91807 (14) | 0.0356 (3) | |
H4 | 0.8735 | 0.3221 | 0.9899 | 0.043* | |
C4A | 0.89714 (17) | 0.30474 (14) | 0.78642 (13) | 0.0320 (3) | |
H4A | 0.8720 | 0.4006 | 0.8028 | 0.038* | |
C5 | 1.04722 (18) | 0.29945 (15) | 0.69682 (14) | 0.0352 (3) | |
O5 | 1.21692 (14) | 0.35060 (14) | 0.73347 (12) | 0.0513 (3) | |
N6 | 0.96070 (17) | 0.23177 (15) | 0.56738 (12) | 0.0414 (3) | |
C7 | 1.0663 (3) | 0.2066 (3) | 0.45696 (19) | 0.0663 (5) | |
H7A | 1.0931 | 0.1134 | 0.4506 | 0.080* | |
H7B | 1.1852 | 0.2864 | 0.4788 | 0.080* | |
C8 | 0.9697 (5) | 0.1996 (3) | 0.3221 (2) | 0.0920 (8) | |
H8A | 0.8776 | 0.1011 | 0.2861 | 0.110* | |
H8B | 1.0616 | 0.2089 | 0.2615 | 0.110* | |
C9 | 0.8730 (4) | 0.3136 (3) | 0.3181 (2) | 0.0914 (8) | |
H9A | 0.9526 | 0.4088 | 0.3778 | 0.110* | |
H9B | 0.8637 | 0.3246 | 0.2268 | 0.110* | |
C10 | 0.6832 (4) | 0.2847 (3) | 0.3564 (2) | 0.0873 (8) | |
H10A | 0.6030 | 0.1913 | 0.2941 | 0.105* | |
H10B | 0.6353 | 0.3632 | 0.3411 | 0.105* | |
C11 | 0.6606 (3) | 0.2749 (2) | 0.4981 (2) | 0.0620 (5) | |
H11A | 0.5277 | 0.2389 | 0.5017 | 0.074* | |
H11B | 0.7103 | 0.3751 | 0.5592 | 0.074* | |
C11A | 0.7550 (2) | 0.17431 (17) | 0.55118 (15) | 0.0423 (3) | |
H11C | 0.7081 | 0.0719 | 0.4914 | 0.051* | |
C11B | 0.72833 (18) | 0.17475 (15) | 0.69564 (14) | 0.0353 (3) | |
O12 | 0.76978 (13) | 0.05080 (10) | 0.73010 (10) | 0.0362 (2) | |
C13 | 1.1022 (2) | 0.24951 (16) | 0.96810 (14) | 0.0369 (3) | |
O13 | 1.15577 (16) | 0.14282 (13) | 0.93999 (12) | 0.0503 (3) | |
O14 | 1.20359 (16) | 0.38062 (13) | 1.05547 (12) | 0.0547 (3) | |
C14 | 1.3882 (3) | 0.3891 (3) | 1.1134 (2) | 0.0785 (7) | |
H14A | 1.4432 | 0.4823 | 1.1823 | 0.118* | |
H14B | 1.4649 | 0.3831 | 1.0437 | 0.118* | |
H14C | 1.3793 | 0.3076 | 1.1528 | 0.118* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0251 (7) | 0.0436 (8) | 0.0698 (11) | 0.0131 (6) | 0.0051 (7) | 0.0090 (7) |
C2 | 0.0352 (8) | 0.0505 (9) | 0.0634 (10) | 0.0136 (6) | 0.0208 (7) | 0.0147 (7) |
C3 | 0.0389 (7) | 0.0414 (8) | 0.0462 (8) | 0.0148 (6) | 0.0143 (6) | 0.0171 (6) |
C4 | 0.0346 (7) | 0.0389 (7) | 0.0350 (7) | 0.0170 (6) | 0.0074 (5) | 0.0063 (5) |
C4A | 0.0276 (6) | 0.0300 (6) | 0.0393 (7) | 0.0131 (5) | 0.0028 (5) | 0.0074 (5) |
C5 | 0.0299 (6) | 0.0378 (7) | 0.0428 (7) | 0.0134 (5) | 0.0052 (5) | 0.0169 (6) |
O5 | 0.0271 (5) | 0.0681 (8) | 0.0603 (7) | 0.0106 (5) | 0.0047 (5) | 0.0266 (6) |
N6 | 0.0388 (7) | 0.0508 (7) | 0.0387 (6) | 0.0172 (6) | 0.0076 (5) | 0.0158 (5) |
C7 | 0.0728 (13) | 0.0911 (15) | 0.0516 (10) | 0.0372 (11) | 0.0287 (9) | 0.0299 (10) |
C8 | 0.153 (3) | 0.0921 (17) | 0.0439 (11) | 0.0550 (17) | 0.0284 (13) | 0.0186 (11) |
C9 | 0.135 (3) | 0.0910 (17) | 0.0566 (12) | 0.0335 (16) | 0.0119 (14) | 0.0391 (12) |
C10 | 0.105 (2) | 0.0797 (15) | 0.0733 (14) | 0.0216 (14) | −0.0235 (14) | 0.0358 (12) |
C11 | 0.0454 (9) | 0.0690 (12) | 0.0734 (12) | 0.0160 (8) | −0.0107 (8) | 0.0323 (10) |
C11A | 0.0372 (7) | 0.0424 (8) | 0.0424 (8) | 0.0088 (6) | −0.0039 (6) | 0.0109 (6) |
C11B | 0.0273 (6) | 0.0330 (7) | 0.0450 (7) | 0.0113 (5) | 0.0011 (5) | 0.0093 (5) |
O12 | 0.0351 (5) | 0.0309 (5) | 0.0438 (5) | 0.0132 (4) | 0.0073 (4) | 0.0085 (4) |
C13 | 0.0395 (7) | 0.0419 (7) | 0.0327 (7) | 0.0179 (6) | 0.0056 (5) | 0.0105 (5) |
O13 | 0.0452 (6) | 0.0456 (6) | 0.0635 (7) | 0.0234 (5) | 0.0030 (5) | 0.0123 (5) |
O14 | 0.0458 (6) | 0.0534 (7) | 0.0541 (7) | 0.0215 (5) | −0.0103 (5) | −0.0062 (5) |
C14 | 0.0509 (11) | 0.0831 (15) | 0.0813 (14) | 0.0250 (10) | −0.0251 (10) | −0.0073 (11) |
C1—C2 | 1.315 (3) | C8—C9 | 1.495 (4) |
C1—C11B | 1.5182 (19) | C8—H8A | 0.9700 |
C1—H1 | 0.9300 | C8—H8B | 0.9700 |
C2—C3 | 1.519 (2) | C9—C10 | 1.484 (4) |
C2—H2 | 0.9300 | C9—H9A | 0.9700 |
C3—O12 | 1.4380 (18) | C9—H9B | 0.9700 |
C3—C4 | 1.567 (2) | C10—C11 | 1.504 (3) |
C3—H3 | 0.9800 | C10—H10A | 0.9700 |
C4—C13 | 1.5062 (19) | C10—H10B | 0.9700 |
C4—C4A | 1.5450 (19) | C11—C11A | 1.531 (2) |
C4—H4 | 0.9800 | C11—H11A | 0.9700 |
C4A—C5 | 1.5226 (18) | C11—H11B | 0.9700 |
C4A—C11B | 1.5508 (18) | C11A—C11B | 1.515 (2) |
C4A—H4A | 0.9800 | C11A—H11C | 0.9800 |
C5—O5 | 1.2228 (17) | C11B—O12 | 1.4386 (16) |
C5—N6 | 1.3502 (19) | C13—O13 | 1.1972 (17) |
N6—C7 | 1.454 (2) | C13—O14 | 1.3389 (18) |
N6—C11A | 1.4718 (19) | O14—C14 | 1.440 (2) |
C7—C8 | 1.490 (3) | C14—H14A | 0.9600 |
C7—H7A | 0.9700 | C14—H14B | 0.9600 |
C7—H7B | 0.9700 | C14—H14C | 0.9600 |
C2—C1—C11B | 105.23 (13) | C10—C9—C8 | 117.5 (2) |
C2—C1—H1 | 127.4 | C10—C9—H9A | 107.9 |
C11B—C1—H1 | 127.4 | C8—C9—H9A | 107.9 |
C1—C2—C3 | 106.25 (13) | C10—C9—H9B | 107.9 |
C1—C2—H2 | 126.9 | C8—C9—H9B | 107.9 |
C3—C2—H2 | 126.9 | H9A—C9—H9B | 107.2 |
O12—C3—C2 | 100.98 (12) | C9—C10—C11 | 118.87 (19) |
O12—C3—C4 | 101.71 (10) | C9—C10—H10A | 107.6 |
C2—C3—C4 | 106.12 (12) | C11—C10—H10A | 107.6 |
O12—C3—H3 | 115.4 | C9—C10—H10B | 107.6 |
C2—C3—H3 | 115.4 | C11—C10—H10B | 107.6 |
C4—C3—H3 | 115.4 | H10A—C10—H10B | 107.0 |
C13—C4—C4A | 115.38 (11) | C10—C11—C11A | 116.12 (18) |
C13—C4—C3 | 112.85 (12) | C10—C11—H11A | 108.3 |
C4A—C4—C3 | 100.04 (11) | C11A—C11—H11A | 108.3 |
C13—C4—H4 | 109.4 | C10—C11—H11B | 108.3 |
C4A—C4—H4 | 109.4 | C11A—C11—H11B | 108.3 |
C3—C4—H4 | 109.4 | H11A—C11—H11B | 107.4 |
C5—C4A—C4 | 119.20 (10) | N6—C11A—C11B | 100.81 (11) |
C5—C4A—C11B | 100.41 (11) | N6—C11A—C11 | 112.40 (13) |
C4—C4A—C11B | 101.76 (10) | C11B—C11A—C11 | 112.17 (14) |
C5—C4A—H4A | 111.4 | N6—C11A—H11C | 110.4 |
C4—C4A—H4A | 111.4 | C11B—C11A—H11C | 110.4 |
C11B—C4A—H4A | 111.4 | C11—C11A—H11C | 110.4 |
O5—C5—N6 | 125.20 (13) | O12—C11B—C11A | 111.09 (11) |
O5—C5—C4A | 126.66 (13) | O12—C11B—C1 | 101.52 (11) |
N6—C5—C4A | 108.11 (11) | C11A—C11B—C1 | 126.86 (12) |
C5—N6—C7 | 121.55 (14) | O12—C11B—C4A | 99.30 (10) |
C5—N6—C11A | 114.43 (12) | C11A—C11B—C4A | 105.24 (11) |
C7—N6—C11A | 123.77 (14) | C1—C11B—C4A | 109.56 (11) |
N6—C7—C8 | 114.54 (19) | C3—O12—C11B | 96.06 (10) |
N6—C7—H7A | 108.6 | O13—C13—O14 | 123.64 (13) |
C8—C7—H7A | 108.6 | O13—C13—C4 | 126.23 (13) |
N6—C7—H7B | 108.6 | O14—C13—C4 | 110.07 (11) |
C8—C7—H7B | 108.6 | C13—O14—C14 | 115.86 (13) |
H7A—C7—H7B | 107.6 | O14—C14—H14A | 109.5 |
C7—C8—C9 | 117.0 (2) | O14—C14—H14B | 109.5 |
C7—C8—H8A | 108.0 | H14A—C14—H14B | 109.5 |
C9—C8—H8A | 108.0 | O14—C14—H14C | 109.5 |
C7—C8—H8B | 108.0 | H14A—C14—H14C | 109.5 |
C9—C8—H8B | 108.0 | H14B—C14—H14C | 109.5 |
H8A—C8—H8B | 107.3 | ||
C11B—C1—C2—C3 | −0.09 (17) | C10—C11—C11A—N6 | 65.8 (2) |
C1—C2—C3—O12 | −32.37 (16) | C10—C11—C11A—C11B | 178.61 (16) |
C1—C2—C3—C4 | 73.37 (16) | N6—C11A—C11B—O12 | −76.52 (13) |
O12—C3—C4—C13 | −91.15 (13) | C11—C11A—C11B—O12 | 163.70 (12) |
C2—C3—C4—C13 | 163.64 (12) | N6—C11A—C11B—C1 | 159.66 (13) |
O12—C3—C4—C4A | 32.02 (12) | C11—C11A—C11B—C1 | 39.9 (2) |
C2—C3—C4—C4A | −73.20 (13) | N6—C11A—C11B—C4A | 30.01 (13) |
C13—C4—C4A—C5 | 17.25 (17) | C11—C11A—C11B—C4A | −89.77 (14) |
C3—C4—C4A—C5 | −104.12 (13) | C2—C1—C11B—O12 | 32.57 (15) |
C13—C4—C4A—C11B | 126.38 (12) | C2—C1—C11B—C11A | 160.29 (14) |
C3—C4—C4A—C11B | 5.01 (12) | C2—C1—C11B—C4A | −71.75 (15) |
C4—C4A—C5—O5 | −49.29 (19) | C5—C4A—C11B—O12 | 82.53 (11) |
C11B—C4A—C5—O5 | −159.17 (14) | C4—C4A—C11B—O12 | −40.49 (11) |
C4—C4A—C5—N6 | 132.54 (12) | C5—C4A—C11B—C11A | −32.47 (12) |
C11B—C4A—C5—N6 | 22.66 (13) | C4—C4A—C11B—C11A | −155.48 (11) |
O5—C5—N6—C7 | 3.1 (2) | C5—C4A—C11B—C1 | −171.63 (11) |
C4A—C5—N6—C7 | −178.69 (14) | C4—C4A—C11B—C1 | 65.35 (13) |
O5—C5—N6—C11A | 177.51 (13) | C2—C3—O12—C11B | 50.39 (12) |
C4A—C5—N6—C11A | −4.29 (16) | C4—C3—O12—C11B | −58.82 (11) |
C5—N6—C7—C8 | −152.76 (19) | C11A—C11B—O12—C3 | 171.91 (11) |
C11A—N6—C7—C8 | 33.4 (3) | C1—C11B—O12—C3 | −50.81 (12) |
N6—C7—C8—C9 | 43.2 (3) | C4A—C11B—O12—C3 | 61.51 (11) |
C7—C8—C9—C10 | −81.4 (3) | C4A—C4—C13—O13 | −91.08 (18) |
C8—C9—C10—C11 | 62.4 (3) | C3—C4—C13—O13 | 23.1 (2) |
C9—C10—C11—C11A | −48.4 (3) | C4A—C4—C13—O14 | 91.77 (14) |
C5—N6—C11A—C11B | −16.60 (16) | C3—C4—C13—O14 | −154.06 (12) |
C7—N6—C11A—C11B | 157.66 (15) | O13—C13—O14—C14 | 1.6 (2) |
C5—N6—C11A—C11 | 103.02 (16) | C4—C13—O14—C14 | 178.86 (16) |
C7—N6—C11A—C11 | −82.7 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1···O5i | 0.93 | 2.59 | 3.4576 (19) | 156 |
C3—H3···O13ii | 0.98 | 2.55 | 3.5259 (19) | 174 |
C4A—H4A···O14iii | 0.98 | 2.51 | 3.4190 (17) | 154 |
C14—H14A···O5iv | 0.96 | 2.56 | 3.279 (2) | 132 |
Symmetry codes: (i) x−1, y, z; (ii) −x+2, −y, −z+2; (iii) −x+2, −y+1, −z+2; (iv) −x+3, −y+1, −z+2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1···O5i | 0.93 | 2.59 | 3.4576 (19) | 156 |
C3—H3···O13ii | 0.98 | 2.55 | 3.5259 (19) | 174 |
C4A—H4A···O14iii | 0.98 | 2.51 | 3.4190 (17) | 154 |
C14—H14A···O5iv | 0.96 | 2.56 | 3.279 (2) | 132 |
Symmetry codes: (i) x−1, y, z; (ii) −x+2, −y, −z+2; (iii) −x+2, −y+1, −z+2; (iv) −x+3, −y+1, −z+2. |
Acknowledgements
Funding from the US National Science Foundation (PREM DMR-0934212 and EPSCoR IIA-1301346) is gratefully acknowledged.
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