research communications
The crystal structures and Hirshfeld surface analysis of 6-(naphthalen-1-yl)-6a-nitro-6,6a,6b,7,9,11a-hexahydrospiro[chromeno[3′,4′:3,4]pyrrolo[1,2-c]thiazole-11,11′-indeno[1,2-b]quinoxaline] and 6′-(naphthalen-1-yl)-6a′-nitro-6′,6a′,6b′,7′,8′,9′,10′,12a′-octahydro-2H-spiro[acenaphthylene-1,12′-chromeno[3,4-a]indolizin]-2-one
aPG & Research Department of Physics, The New College (Autonomous), University of Madras, Chennai 600 014, Tamil Nadu, India, and bDepartment of Biophysics, All India Institute of Medical Science, New Delhi 110029, India
*Correspondence e-mail: mnizam.new@gmail.com
The title compounds, 6-(naphthalen-1-yl)-6a-nitro-6,6a,6 b,7,9,11a-hexahydrospiro[chromeno[3′,4′:3,4]pyrrolo[1,2-c]thiazole-11,11′-indeno[1,2-b]quinoxaline], C37H26N4O3S, (I), and 6′-(naphthalen-1-yl)-6a′-nitro-6′,6a′,6b′,7′,8′,9′,10′,12a′-octahydro-2H-spiro[acenaphthylene-1,12′-chromeno[3,4-a]indolizin]-2-one, C36H28N2O4, (II), are new spiro derivatives, in which both the pyrrolidine rings adopt twisted conformations. In (I), the five-membered thiazole ring adopts an while the eight-membered pyrrolidine-thiazole ring adopts a boat conformation. An intramolecular C—H⋯N hydrogen bond occurs, involving a C atom of the pyran ring and an N atom of the pyrazine ring. In (II), the six-membered piperidine ring adopts a chair conformation. An intramolecular C—H⋯O hydrogen bond occurs, involving a C atom of the pyrrolidine ring and the keto O atom. For both compounds, the is stabilized by intermolecular C—H⋯O hydrogen bonds. In (I), the C—H⋯O hydrogen bonds link adjacent molecules, forming R22(16) loops propagating along the b-axis direction, while in (II) they form zigzag chains along the b-axis direction. In both compounds, C—H⋯π interactions help to consolidate the structure, but no significant π–π interactions with centroid–centroid distances of less than 4 Å are observed.
Keywords: crystal structure; nitrogen-containing heterocycles; chromen; spiro compounds; cycloaddition; piperidine; pyran; pyrrolidine; hydrogen bonding; C—H⋯π interactions; Hirshfeld surface analysis.
1. Chemical context
Nitrogen-containing heterocycles and their derivatives are present in many large molecules suitable for photo-chemical, electrochemical and catalytic applications; moreover, some derivatives also possess non-linear optical (NLO) properties (Babu et al., 2014a,b). are potential precursors for biologically important compounds such as (NizamMohideen et al., 2009a; Ali et al., 1988), (NizamMohideen et al., 2009c; Goti et al., 1997), and exhibit antibacterial and antifungal activities (Ravi Kumar et al., 2003). The 1,3-dipolar cycloaddition of nitrones with olefinic dipolarophiles proceeds through a concerted mechanism yielding highly substituted (Gothelf & Jørgensen, 1998). The cornerstone for cycloaddition reactions, nitrones, are excellent for (NizamMohideen et al., 2009b; Bernotas et al., 1996) and are highly versatile synthetic intermediates (Breuer, 1982). The stereochemistry, such as regioselectivity and enantioselectivity, of (Huisgen, 1984) can be studied by 1,3-dipolar cycloaddition reactions. Against this background and considering the importance of their natural occurrence, biological, pharmacological and medicinal activities, use as synthetic intermediates, as well as in view of our ongoing research on the design of novel heterocycles, we have synthesized the title compounds and report herein their crystal structures.
2. Structural commentary
The bond lengths and angles are close to those reported for similar compounds (Devi et al., 2013a,b; Syed Abuthahir et al., 2019a,b). In both compounds, the five-membered pyrrolidine ring (N3/C1/C16/C24/C25) adopts a twisted conformation [on C24 and C25 in (I) and on C17 and N1 in (II)], with a pseudo-twofold axis passing through the N3—C1 and N1—C12 bonds, respectively. The puckering parameters are: q2 = 0.357 (2) Å, φ = 307.0 (3)° for (I) and q2 = 0.415 (2) Å, φ = 348.5 (3)° for (II). The mean plane of the pyrrolidine ring is almost perpendicular to the mean plane of the cyclopentene ring (C1/C2/C7/C8/C15), being inclined by 88.5 (2) in (I) and 84.3 (2)° in (II). It forms dihedral angles of 57.7 (2) in (I) and 63.0 (2)° in (II) with the mean plane of the pyran ring (O1/C16/C17/C22–C24), and subtends dihedral angles of 24.2 (2) in (I) and 45.3 (2)° in (II) with the mean plane of the naphthalene ring system (C28–C37). The mean plane of the pyran ring is inclined to the mean plane of the cyclopentene ring by 55.2 (2) in (I) and 36.7 (2)° in (II), while it subtends dihedral angles of 64.3 (2) in (I) and 81.0 (2)° in (II) with the mean plane of the naphthalene unit.
In (I), the five-membered thiazole ring (S1/C25–C27/N3) adopts an on C25 with a pseudo-twofold axis passing through the S1—C26 bond. Its puckering parameters are q2 = 0.391 (2) Å and φ = 251.9 (3)°. The eight-membered pyrrolidine-thiazole ring (S1/C24–C27/C1/C16/N3) adopts a boat conformation with a total puckering amplitude Q = 1.351 (2) Å and φ = 321.43 (8)°. The mean planes of the pyran and thiazole rings are inclined to each other by 77.5 (2)°. The mean plane of the pyrazine ring (N1/N2/C8/C9/C14/C15) forms a dihedral angle of 57.1 (2)° with the mean plane of the pyran ring, while it is almost perpendicular with respect to the mean plane of the pyrrolidine ring, forming an angle of 89.8 (2)°. The pyrazine ring is inclined by 51.9 (2), 1.9 (2) and 69.5 (2)° with respect to the mean planes of the thiazole and cyclopentene ring and the naphthalene ring system, respectively. An intramolecular C23–H23⋯N1 hydrogen bond is formed (Fig. 1).
In (II), the six-membered piperidine ring (N1/C13–C17) adopts a chair conformation with puckering parameters q2 = 0.045 (2) Å, θ = 175.7 (2)° and φ = 22 (3)°. The dihedral angle between the acenaphthylene (C1–C12) and naphthalene (C27–C36) ring systems is 63.8 (6)°. Moreover, this moiety is inclined of 85.3 (1), 36.1 (1) and 89.4 (2) ° with respect to the mean planes of the pyrrolidine (N1/C12/C17–C19), pyran (O4/C18–C20/C25/C26) and piperidine (N1/C13–C17) rings, respectively. The keto atom O1 deviates from the mean plane of the acenaphthylene unit by 0.148 (1) Å. An intramolecular C17—H17⋯O1 hydrogen bond is present (Fig. 2).
3. Supramolecular features
For both compounds, the and 2). In (I), the C—H⋯O hydrogen bonds link adjacent molecules, forming R22(16) loops propagating along the b-axis direction. The loops are linked by C—H⋯S hydrogen bonds, forming layers parallel to the (101) plane; C—H⋯π interactions are present within the layers (Table 1, Fig. 3).
is stabilized by intermolecular C—H⋯O hydrogen bonds (Tables 1
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In the crystal of (II), molecules are linked by C—H⋯O interactions, forming zigzag chains along the b-axis direction (Fig. 4 and Table 2). A C—H⋯π interaction links the chains to form layers parallel to (100), yielding a three-dimensional supramolecular structure. No significant π–π interactions with centroid–centroid distances of less than 4 Å were observed in either compound.
4. Hirshfeld surface analysis
The Hirshfeld surface analysis (Spackman & Jayatilaka, 2009), and the associated two-dimensional fingerprint plots (McKinnon et al., 2007), employed to analyse the intermolecular contacts in the crystals, were performed with CrystalExplorer17 (Turner et al., 2017).
The Hirshfeld surfaces of (I) and (II) mapped over dnorm are given in Figs. 5 and 6, respectively, while the intermolecular contacts are illustrated in Fig. 7 for (I) and in Fig. 8 for (II). They are colour-mapped with the normalized contact distance, dnorm, varying from red (distances shorter than the sum of the van der Waals radii) through white to blue (distances longer than the sum of the van der Waals radii). The red spots on the surface indicate the intermolecular contacts involved in hydrogen bonding.
The fingerprint plots for the two compounds are given in Figs. 9 and 10. For (I), they reveal that the principal intermolecular contacts are H⋯H (44.9%, Fig. 9b), C⋯H/H⋯C (25.0%, Fig. 9c), O⋯H/H⋯O (11.8%, Fig. 9d), S⋯H/H⋯S (5.4%, Fig. 9e) and N⋯H/H⋯N (4.0%, Fig. 9f), followed by the C⋯C contacts (3.5%, Fig. 9g). For (II), they reveal a similar trend, with the principal intermolecular contacts being H⋯H (56.4%, Fig. 10b), C⋯H/H⋯C (21.9%, Fig. 10c), O⋯H/H⋯O (14.5%, Fig. 10d), followed by the C⋯C contacts (0.9%, Fig. 10e). In both compounds the H⋯H intermolecular contacts predominate.
5. Database survey
A search of the Cambridge Structural Database (CSD, Version 5.39, August 2018; Groom et al., 2016) for the 6′-(4-phenyl)-6a′-hexahydro-2H,6′H,6b′H-spiro[benzopyrano[3,4-a]indolizin]-2-one skeleton yielded five hits: namely 6-(4- methoxyphenyl)-6a-nitro-6,6a,6b,7,8,9,10,12a-octahydrospiro-[chromeno[3,4-a]indolizine-12,3-indolin]-2-one (AFONEQ; Devi et al., 2013a) and 6-(4-methoxyphenyl)-6a-nitro-6,6a,6b,7,8,9,10,12a-octahydrospiro[chromeno[3,4-a]indolizine-12,3-indolin]-2-one (FIDCOM; Devi et al., 2013b). In addition, the crystal structures of 6-(naphthalen-1-yl)-6a-nitro-6,6a,6b,7,9,11a-hexahydrospiro[chromeno[3′,4′:3,4]pyrrolo [1,2-c]thiazole-11,11′-indeno[1,2-b]quinoxaline] (XITKUJ and XITKOD; Syed Abuthahir et al., 2019a) and 6′-(naphthalen-1-yl)-6a′-nitro-6′,6a′,6b′,7′,8′,9′,10′,12a′-octahydro-2H-spiro[acenaphthylene-1,12′-chromeno[3,4-a]indolizin]-2-one (XIWRUT01; Syed Abuthahir et al., 2019b) were recently reported by some of us. The bond lengths and bond angles are very similar to those reported here for the title compounds.
6. Synthesis and crystallization
Compound (I): to a solution of indenoquinoxalinone (0.232 g, 1.0 mmol) and thiazolidine-4-carboxylic acid (0.199 g, 1.5 mmol) in dry toluene, 0.302 g (1.0 mmol) of 2-(naphthalen-1-yl)-3-nitro-2H-chromene were added under a nitrogen atmosphere.
Compound (II): to a solution of acenaphthoquinone (0.182 g, 1.0 mmol) and pipacolinic acid (0.193 g, 1.5 mmol) in dry toluene, (0.302 g, 1 mmol) of 2-(naphthalen-1-yl)-3-nitro-2H-chromene were added under a nitrogen atmosphere.
The solutions were refluxed for 18 h in a Dean–Stark apparatus to give the cycloadducts. After completion of the reactions as indicated by TLC, the solvent was evaporated under reduced pressure. The crude products obtained were purified by
using hexane/EtOAc (7:3) as (yield 84%). Colourless block-like crystals of the title compounds, suitable for X-ray were obtained by slow evaporation of solutions in ethanol.7. Refinement
Crystal data, data collection and structure . All H atoms were positioned geometrically, with N—H = 0.86 Å, C—H = 0.93-0.97 Å, and constrained to ride on their parent atoms with Uiso(H) = 1.5Ueq(C-methyl) and 1.2Ueq(N, C) for all other H atoms.
details are summarized in Table 3
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Supporting information
https://doi.org/10.1107/S205698901901291X/xi2018sup1.cif
contains datablocks global, I, II. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S205698901901291X/xi2018Isup2.hkl
Structure factors: contains datablock II. DOI: https://doi.org/10.1107/S205698901901291X/xi2018IIsup3.hkl
Supporting information file. DOI: https://doi.org/10.1107/S205698901901291X/xi2018Isup4.cml
Supporting information file. DOI: https://doi.org/10.1107/S205698901901291X/xi2018IIsup5.cml
For both structures, data collection: APEX2 (Bruker, 2008); cell
SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXT2018 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008). Software used to prepare material for publication: WinGX (Farrugia, 2012), publCIF (Westrip, 2010) and PLATON (Spek, 2009 for (I); WinGX (Farrugia, 2012), publCIF (Westrip, 2010) and PLATON (Spek, 2009) for (II).C37H26N4O3S | F(000) = 1264 |
Mr = 606.68 | Dx = 1.246 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 8.3690 (3) Å | Cell parameters from 8083 reflections |
b = 13.2440 (4) Å | θ = 1.8–26.9° |
c = 29.2210 (5) Å | µ = 0.14 mm−1 |
β = 93.280 (2)° | T = 293 K |
V = 3233.52 (16) Å3 | Block, colourless |
Z = 4 | 0.25 × 0.20 × 0.15 mm |
Bruker Kappa APEXII CCD diffractometer | 4209 reflections with I > 2σ(I) |
ω and φ scans | Rint = 0.061 |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | θmax = 28.6°, θmin = 1.4° |
Tmin = 0.741, Tmax = 0.852 | h = −11→10 |
30398 measured reflections | k = −14→17 |
8083 independent reflections | l = −39→39 |
Refinement on F2 | 1 restraint |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.057 | H-atom parameters constrained |
wR(F2) = 0.164 | w = 1/[σ2(Fo2) + (0.0738P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
8083 reflections | Δρmax = 0.36 e Å−3 |
406 parameters | Δρmin = −0.34 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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.1161 (2) | 0.24359 (15) | 0.30919 (6) | 0.0494 (5) | |
C2 | 0.0918 (2) | 0.23613 (16) | 0.25673 (7) | 0.0541 (5) | |
C3 | 0.1107 (3) | 0.15404 (18) | 0.22850 (7) | 0.0671 (6) | |
H3 | 0.139426 | 0.091580 | 0.240969 | 0.081* | |
C4 | 0.0865 (3) | 0.1652 (2) | 0.18134 (8) | 0.0849 (8) | |
H4 | 0.098128 | 0.109992 | 0.162138 | 0.102* | |
C5 | 0.0448 (3) | 0.2591 (3) | 0.16285 (9) | 0.0936 (9) | |
H5 | 0.031066 | 0.266237 | 0.131206 | 0.112* | |
C6 | 0.0239 (3) | 0.3398 (2) | 0.18991 (9) | 0.0859 (8) | |
H6 | −0.007778 | 0.401526 | 0.177193 | 0.103* | |
C7 | 0.0505 (2) | 0.32971 (17) | 0.23738 (7) | 0.0614 (6) | |
C8 | 0.0423 (2) | 0.40471 (18) | 0.27342 (8) | 0.0610 (6) | |
C9 | 0.0036 (3) | 0.55087 (19) | 0.31022 (12) | 0.0825 (8) | |
C10 | −0.0465 (4) | 0.6527 (2) | 0.31060 (17) | 0.1145 (11) | |
H10 | −0.076570 | 0.684749 | 0.283137 | 0.137* | |
C11 | −0.0510 (5) | 0.7035 (3) | 0.3502 (2) | 0.1415 (17) | |
H11 | −0.084652 | 0.770462 | 0.349812 | 0.170* | |
C12 | −0.0066 (5) | 0.6582 (3) | 0.3912 (2) | 0.1382 (15) | |
H12 | −0.010154 | 0.695207 | 0.418145 | 0.166* | |
C13 | 0.0430 (4) | 0.5595 (2) | 0.39324 (12) | 0.1058 (10) | |
H13 | 0.073851 | 0.529893 | 0.421227 | 0.127* | |
C14 | 0.0463 (3) | 0.50397 (19) | 0.35256 (10) | 0.0750 (7) | |
C15 | 0.0833 (2) | 0.35657 (16) | 0.31577 (8) | 0.0541 (5) | |
C16 | 0.2865 (2) | 0.20774 (14) | 0.32709 (6) | 0.0472 (5) | |
H16 | 0.325781 | 0.161182 | 0.304208 | 0.057* | |
C17 | 0.4111 (2) | 0.28888 (15) | 0.33502 (7) | 0.0517 (5) | |
C18 | 0.4752 (2) | 0.33919 (18) | 0.29859 (8) | 0.0670 (6) | |
H18 | 0.439990 | 0.323138 | 0.268711 | 0.080* | |
C19 | 0.5897 (3) | 0.4123 (2) | 0.30622 (9) | 0.0801 (7) | |
H19 | 0.631402 | 0.445264 | 0.281466 | 0.096* | |
C20 | 0.6434 (3) | 0.4371 (2) | 0.35007 (10) | 0.0846 (8) | |
H20 | 0.720422 | 0.487177 | 0.355019 | 0.102* | |
C21 | 0.5830 (3) | 0.38786 (18) | 0.38640 (9) | 0.0722 (7) | |
H21 | 0.619996 | 0.403698 | 0.416151 | 0.087* | |
C22 | 0.4672 (2) | 0.31471 (16) | 0.37893 (7) | 0.0556 (5) | |
C23 | 0.2641 (2) | 0.21920 (14) | 0.41284 (6) | 0.0472 (5) | |
H23 | 0.182414 | 0.271326 | 0.406921 | 0.057* | |
C24 | 0.25919 (19) | 0.14506 (12) | 0.37099 (6) | 0.0446 (4) | |
C25 | 0.0895 (2) | 0.10286 (14) | 0.36166 (6) | 0.0482 (5) | |
H25 | 0.040553 | 0.091076 | 0.390862 | 0.058* | |
C26 | 0.0710 (3) | 0.00792 (16) | 0.33174 (7) | 0.0591 (5) | |
H26A | 0.088186 | −0.052686 | 0.350003 | 0.071* | |
H26B | 0.146009 | 0.008585 | 0.307642 | 0.071* | |
C27 | −0.1468 (2) | 0.15173 (17) | 0.31845 (8) | 0.0665 (6) | |
H27A | −0.174584 | 0.186668 | 0.289926 | 0.080* | |
H27B | −0.228995 | 0.165400 | 0.339706 | 0.080* | |
C28 | 0.2370 (2) | 0.17076 (14) | 0.45860 (6) | 0.0466 (5) | |
C29 | 0.3636 (3) | 0.12777 (16) | 0.48297 (7) | 0.0579 (5) | |
H29 | 0.463434 | 0.127450 | 0.470563 | 0.069* | |
C30 | 0.3470 (3) | 0.08386 (17) | 0.52642 (7) | 0.0670 (6) | |
H30 | 0.435212 | 0.056120 | 0.542655 | 0.080* | |
C31 | 0.2015 (3) | 0.08258 (16) | 0.54417 (7) | 0.0621 (6) | |
H31 | 0.190245 | 0.052815 | 0.572633 | 0.074* | |
C32 | 0.0676 (2) | 0.12492 (14) | 0.52078 (6) | 0.0523 (5) | |
C33 | −0.0829 (3) | 0.12485 (18) | 0.53942 (7) | 0.0656 (6) | |
H33 | −0.094090 | 0.094106 | 0.567672 | 0.079* | |
C34 | −0.2109 (3) | 0.1675 (2) | 0.51796 (8) | 0.0789 (7) | |
H34 | −0.309462 | 0.165333 | 0.531071 | 0.095* | |
C35 | −0.1964 (3) | 0.21564 (19) | 0.47545 (8) | 0.0747 (7) | |
H35 | −0.285147 | 0.246448 | 0.460805 | 0.090* | |
C36 | −0.0535 (2) | 0.21727 (16) | 0.45578 (7) | 0.0582 (5) | |
H36 | −0.045876 | 0.249053 | 0.427606 | 0.070* | |
C37 | 0.0839 (2) | 0.17177 (13) | 0.47715 (6) | 0.0460 (5) | |
N1 | 0.0872 (2) | 0.40293 (14) | 0.35511 (7) | 0.0660 (5) | |
N2 | 0.0036 (2) | 0.49945 (16) | 0.26964 (8) | 0.0773 (6) | |
N3 | 0.00650 (17) | 0.18572 (12) | 0.33735 (5) | 0.0503 (4) | |
N4 | 0.37670 (19) | 0.06748 (12) | 0.37895 (5) | 0.0512 (4) | |
O1 | 0.41679 (16) | 0.26684 (11) | 0.41708 (4) | 0.0619 (4) | |
O2 | 0.51538 (18) | 0.08236 (11) | 0.36905 (6) | 0.0754 (5) | |
O3 | 0.33881 (17) | −0.01166 (11) | 0.39739 (5) | 0.0637 (4) | |
S1 | −0.13165 (8) | 0.01440 (5) | 0.30819 (2) | 0.0791 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0494 (11) | 0.0584 (13) | 0.0412 (10) | −0.0039 (9) | 0.0084 (9) | 0.0061 (9) |
C2 | 0.0503 (12) | 0.0696 (14) | 0.0425 (11) | −0.0071 (10) | 0.0034 (9) | 0.0093 (10) |
C3 | 0.0787 (15) | 0.0808 (16) | 0.0424 (12) | −0.0018 (12) | 0.0073 (11) | 0.0045 (11) |
C4 | 0.0974 (19) | 0.110 (2) | 0.0471 (14) | −0.0118 (16) | 0.0034 (13) | −0.0004 (14) |
C5 | 0.113 (2) | 0.125 (3) | 0.0428 (14) | −0.0156 (18) | 0.0011 (14) | 0.0160 (17) |
C6 | 0.0889 (19) | 0.106 (2) | 0.0622 (17) | −0.0077 (15) | −0.0052 (14) | 0.0348 (16) |
C7 | 0.0522 (13) | 0.0786 (16) | 0.0534 (13) | −0.0104 (11) | 0.0015 (10) | 0.0171 (12) |
C8 | 0.0456 (12) | 0.0651 (16) | 0.0719 (15) | −0.0070 (10) | 0.0005 (10) | 0.0185 (12) |
C9 | 0.0619 (16) | 0.0558 (17) | 0.130 (3) | −0.0140 (12) | 0.0078 (16) | 0.0102 (17) |
C10 | 0.100 (2) | 0.059 (2) | 0.184 (4) | −0.0076 (16) | 0.007 (2) | 0.015 (2) |
C11 | 0.134 (3) | 0.056 (2) | 0.235 (6) | −0.007 (2) | 0.020 (3) | −0.013 (3) |
C12 | 0.135 (3) | 0.079 (3) | 0.201 (5) | −0.013 (2) | 0.019 (3) | −0.057 (3) |
C13 | 0.113 (2) | 0.075 (2) | 0.129 (3) | −0.0083 (16) | 0.0026 (19) | −0.0351 (18) |
C14 | 0.0578 (15) | 0.0589 (17) | 0.109 (2) | −0.0086 (11) | 0.0058 (13) | −0.0062 (15) |
C15 | 0.0417 (11) | 0.0601 (14) | 0.0606 (13) | −0.0059 (9) | 0.0040 (9) | 0.0053 (11) |
C16 | 0.0443 (11) | 0.0593 (12) | 0.0388 (10) | −0.0001 (9) | 0.0087 (8) | 0.0067 (9) |
C17 | 0.0411 (11) | 0.0617 (13) | 0.0528 (12) | −0.0031 (9) | 0.0087 (9) | 0.0111 (10) |
C18 | 0.0544 (13) | 0.0859 (16) | 0.0617 (14) | −0.0054 (12) | 0.0137 (10) | 0.0237 (12) |
C19 | 0.0638 (15) | 0.100 (2) | 0.0775 (18) | −0.0176 (14) | 0.0161 (13) | 0.0349 (14) |
C20 | 0.0656 (16) | 0.0879 (19) | 0.101 (2) | −0.0264 (13) | 0.0080 (14) | 0.0270 (15) |
C21 | 0.0594 (14) | 0.0815 (16) | 0.0751 (16) | −0.0216 (12) | −0.0003 (12) | 0.0125 (12) |
C22 | 0.0478 (11) | 0.0656 (14) | 0.0536 (13) | −0.0129 (10) | 0.0062 (9) | 0.0096 (10) |
C23 | 0.0471 (11) | 0.0532 (12) | 0.0414 (10) | −0.0103 (9) | 0.0039 (8) | 0.0013 (8) |
C24 | 0.0446 (11) | 0.0522 (11) | 0.0374 (10) | −0.0006 (9) | 0.0064 (8) | 0.0052 (8) |
C25 | 0.0511 (11) | 0.0581 (12) | 0.0357 (10) | −0.0109 (9) | 0.0063 (8) | 0.0007 (9) |
C26 | 0.0691 (14) | 0.0637 (14) | 0.0451 (11) | −0.0129 (10) | 0.0079 (10) | −0.0040 (9) |
C27 | 0.0500 (13) | 0.0894 (17) | 0.0599 (14) | −0.0130 (11) | 0.0024 (10) | 0.0090 (11) |
C28 | 0.0513 (12) | 0.0513 (11) | 0.0372 (10) | −0.0065 (9) | 0.0027 (9) | −0.0014 (8) |
C29 | 0.0536 (12) | 0.0751 (14) | 0.0451 (11) | −0.0008 (11) | 0.0038 (10) | 0.0002 (10) |
C30 | 0.0722 (16) | 0.0801 (16) | 0.0479 (12) | 0.0037 (12) | −0.0027 (11) | 0.0071 (11) |
C31 | 0.0766 (16) | 0.0703 (15) | 0.0394 (11) | −0.0079 (12) | 0.0037 (11) | 0.0063 (10) |
C32 | 0.0638 (13) | 0.0558 (12) | 0.0376 (10) | −0.0159 (10) | 0.0047 (10) | −0.0043 (9) |
C33 | 0.0643 (15) | 0.0885 (17) | 0.0446 (12) | −0.0236 (12) | 0.0082 (11) | −0.0002 (11) |
C34 | 0.0611 (15) | 0.118 (2) | 0.0595 (15) | −0.0158 (14) | 0.0195 (12) | −0.0035 (14) |
C35 | 0.0548 (14) | 0.1079 (19) | 0.0618 (15) | 0.0005 (12) | 0.0062 (11) | 0.0050 (13) |
C36 | 0.0548 (13) | 0.0741 (14) | 0.0461 (11) | −0.0036 (11) | 0.0069 (10) | 0.0040 (10) |
C37 | 0.0506 (11) | 0.0487 (11) | 0.0389 (10) | −0.0108 (9) | 0.0036 (9) | −0.0045 (8) |
N1 | 0.0608 (11) | 0.0621 (13) | 0.0754 (14) | −0.0053 (9) | 0.0074 (10) | −0.0065 (10) |
N2 | 0.0665 (13) | 0.0621 (14) | 0.1031 (18) | −0.0071 (10) | 0.0031 (11) | 0.0214 (12) |
N3 | 0.0424 (9) | 0.0652 (11) | 0.0437 (9) | −0.0082 (8) | 0.0065 (7) | 0.0062 (8) |
N4 | 0.0532 (11) | 0.0584 (11) | 0.0425 (9) | −0.0018 (9) | 0.0063 (8) | 0.0021 (8) |
O1 | 0.0589 (9) | 0.0785 (10) | 0.0483 (8) | −0.0286 (7) | 0.0026 (6) | 0.0055 (7) |
O2 | 0.0502 (9) | 0.0822 (11) | 0.0953 (12) | 0.0063 (7) | 0.0185 (8) | 0.0192 (9) |
O3 | 0.0709 (10) | 0.0622 (9) | 0.0586 (9) | −0.0008 (7) | 0.0085 (7) | 0.0144 (7) |
S1 | 0.0740 (4) | 0.0978 (5) | 0.0647 (4) | −0.0289 (3) | −0.0022 (3) | −0.0161 (3) |
C1—N3 | 1.481 (2) | C20—H20 | 0.9300 |
C1—C15 | 1.535 (3) | C21—C22 | 1.379 (3) |
C1—C2 | 1.538 (3) | C21—H21 | 0.9300 |
C1—C16 | 1.564 (3) | C22—O1 | 1.369 (2) |
C2—C3 | 1.379 (3) | C23—O1 | 1.424 (2) |
C2—C7 | 1.397 (3) | C23—C28 | 1.512 (2) |
C3—C4 | 1.389 (3) | C23—C24 | 1.567 (2) |
C3—H3 | 0.9300 | C23—H23 | 0.9800 |
C4—C5 | 1.393 (4) | C24—N4 | 1.4321 (9) |
C4—H4 | 0.9300 | C24—C25 | 1.536 (2) |
C5—C6 | 1.347 (4) | C25—N3 | 1.461 (2) |
C5—H5 | 0.9300 | C25—C26 | 1.534 (3) |
C6—C7 | 1.399 (3) | C25—H25 | 0.9800 |
C6—H6 | 0.9300 | C26—S1 | 1.795 (2) |
C7—C8 | 1.452 (3) | C26—H26A | 0.9700 |
C8—N2 | 1.299 (3) | C26—H26B | 0.9700 |
C8—C15 | 1.417 (3) | C27—N3 | 1.439 (2) |
C9—N2 | 1.367 (3) | C27—S1 | 1.849 (2) |
C9—C10 | 1.412 (4) | C27—H27A | 0.9700 |
C9—C14 | 1.412 (4) | C27—H27B | 0.9700 |
C10—C11 | 1.340 (6) | C28—C29 | 1.366 (3) |
C10—H10 | 0.9300 | C28—C37 | 1.420 (3) |
C11—C12 | 1.373 (6) | C29—C30 | 1.411 (3) |
C11—H11 | 0.9300 | C29—H29 | 0.9300 |
C12—C13 | 1.372 (5) | C30—C31 | 1.351 (3) |
C12—H12 | 0.9300 | C30—H30 | 0.9300 |
C13—C14 | 1.399 (4) | C31—C32 | 1.396 (3) |
C13—H13 | 0.9300 | C31—H31 | 0.9300 |
C14—N1 | 1.382 (3) | C32—C33 | 1.401 (3) |
C15—N1 | 1.302 (3) | C32—C37 | 1.431 (3) |
C16—C17 | 1.506 (3) | C33—C34 | 1.335 (3) |
C16—C24 | 1.556 (2) | C33—H33 | 0.9300 |
C16—H16 | 0.9800 | C34—C35 | 1.408 (3) |
C17—C22 | 1.384 (3) | C34—H34 | 0.9300 |
C17—C18 | 1.389 (3) | C35—C36 | 1.356 (3) |
C18—C19 | 1.371 (3) | C35—H35 | 0.9300 |
C18—H18 | 0.9300 | C36—C37 | 1.412 (3) |
C19—C20 | 1.374 (3) | C36—H36 | 0.9300 |
C19—H19 | 0.9300 | N4—O2 | 1.2279 (19) |
C20—C21 | 1.368 (3) | N4—O3 | 1.2285 (19) |
N3—C1—C15 | 108.30 (15) | C21—C22—C17 | 121.22 (19) |
N3—C1—C2 | 118.02 (15) | O1—C23—C28 | 106.87 (14) |
C15—C1—C2 | 99.97 (15) | O1—C23—C24 | 109.20 (14) |
N3—C1—C16 | 103.82 (14) | C28—C23—C24 | 115.20 (15) |
C15—C1—C16 | 114.83 (15) | O1—C23—H23 | 108.5 |
C2—C1—C16 | 112.33 (15) | C28—C23—H23 | 108.5 |
C3—C2—C7 | 119.43 (19) | C24—C23—H23 | 108.5 |
C3—C2—C1 | 129.31 (19) | N4—C24—C25 | 112.77 (15) |
C7—C2—C1 | 111.21 (18) | N4—C24—C16 | 112.63 (14) |
C2—C3—C4 | 119.6 (2) | C25—C24—C16 | 103.05 (13) |
C2—C3—H3 | 120.2 | N4—C24—C23 | 109.61 (14) |
C4—C3—H3 | 120.2 | C25—C24—C23 | 110.44 (13) |
C3—C4—C5 | 119.9 (2) | C16—C24—C23 | 108.10 (14) |
C3—C4—H4 | 120.0 | N3—C25—C26 | 107.98 (15) |
C5—C4—H4 | 120.0 | N3—C25—C24 | 102.83 (13) |
C6—C5—C4 | 121.3 (2) | C26—C25—C24 | 117.50 (16) |
C6—C5—H5 | 119.4 | N3—C25—H25 | 109.4 |
C4—C5—H5 | 119.4 | C26—C25—H25 | 109.4 |
C5—C6—C7 | 119.2 (2) | C24—C25—H25 | 109.4 |
C5—C6—H6 | 120.4 | C25—C26—S1 | 104.00 (14) |
C7—C6—H6 | 120.4 | C25—C26—H26A | 111.0 |
C2—C7—C6 | 120.5 (2) | S1—C26—H26A | 111.0 |
C2—C7—C8 | 109.52 (19) | C25—C26—H26B | 111.0 |
C6—C7—C8 | 130.0 (2) | S1—C26—H26B | 111.0 |
N2—C8—C15 | 123.8 (2) | H26A—C26—H26B | 109.0 |
N2—C8—C7 | 128.4 (2) | N3—C27—S1 | 107.58 (14) |
C15—C8—C7 | 107.9 (2) | N3—C27—H27A | 110.2 |
N2—C9—C10 | 119.8 (3) | S1—C27—H27A | 110.2 |
N2—C9—C14 | 121.9 (2) | N3—C27—H27B | 110.2 |
C10—C9—C14 | 118.3 (3) | S1—C27—H27B | 110.2 |
C11—C10—C9 | 120.6 (4) | H27A—C27—H27B | 108.5 |
C11—C10—H10 | 119.7 | C29—C28—C37 | 119.65 (17) |
C9—C10—H10 | 119.7 | C29—C28—C23 | 119.15 (17) |
C10—C11—C12 | 120.9 (4) | C37—C28—C23 | 121.18 (16) |
C10—C11—H11 | 119.5 | C28—C29—C30 | 121.9 (2) |
C12—C11—H11 | 119.5 | C28—C29—H29 | 119.1 |
C13—C12—C11 | 121.4 (4) | C30—C29—H29 | 119.1 |
C13—C12—H12 | 119.3 | C31—C30—C29 | 119.2 (2) |
C11—C12—H12 | 119.3 | C31—C30—H30 | 120.4 |
C12—C13—C14 | 118.9 (4) | C29—C30—H30 | 120.4 |
C12—C13—H13 | 120.5 | C30—C31—C32 | 121.53 (19) |
C14—C13—H13 | 120.5 | C30—C31—H31 | 119.2 |
N1—C14—C13 | 118.7 (3) | C32—C31—H31 | 119.2 |
N1—C14—C9 | 121.5 (2) | C31—C32—C33 | 121.59 (19) |
C13—C14—C9 | 119.8 (3) | C31—C32—C37 | 119.71 (18) |
N1—C15—C8 | 123.5 (2) | C33—C32—C37 | 118.69 (19) |
N1—C15—C1 | 125.07 (19) | C34—C33—C32 | 122.1 (2) |
C8—C15—C1 | 111.42 (19) | C34—C33—H33 | 118.9 |
C17—C16—C24 | 112.77 (15) | C32—C33—H33 | 118.9 |
C17—C16—C1 | 116.40 (16) | C33—C34—C35 | 119.9 (2) |
C24—C16—C1 | 105.28 (13) | C33—C34—H34 | 120.0 |
C17—C16—H16 | 107.3 | C35—C34—H34 | 120.0 |
C24—C16—H16 | 107.3 | C36—C35—C34 | 120.2 (2) |
C1—C16—H16 | 107.3 | C36—C35—H35 | 119.9 |
C22—C17—C18 | 117.82 (19) | C34—C35—H35 | 119.9 |
C22—C17—C16 | 120.94 (16) | C35—C36—C37 | 121.41 (19) |
C18—C17—C16 | 121.24 (19) | C35—C36—H36 | 119.3 |
C19—C18—C17 | 120.7 (2) | C37—C36—H36 | 119.3 |
C19—C18—H18 | 119.6 | C36—C37—C28 | 124.43 (17) |
C17—C18—H18 | 119.6 | C36—C37—C32 | 117.55 (17) |
C18—C19—C20 | 120.6 (2) | C28—C37—C32 | 118.01 (17) |
C18—C19—H19 | 119.7 | C15—N1—C14 | 114.5 (2) |
C20—C19—H19 | 119.7 | C8—N2—C9 | 114.8 (2) |
C21—C20—C19 | 119.6 (2) | C27—N3—C25 | 109.89 (15) |
C21—C20—H20 | 120.2 | C27—N3—C1 | 121.03 (15) |
C19—C20—H20 | 120.2 | C25—N3—C1 | 111.50 (14) |
C20—C21—C22 | 120.0 (2) | O2—N4—O3 | 120.76 (14) |
C20—C21—H21 | 120.0 | O2—N4—C24 | 119.74 (16) |
C22—C21—H21 | 120.0 | O3—N4—C24 | 119.43 (15) |
O1—C22—C21 | 116.28 (19) | C22—O1—C23 | 116.79 (14) |
O1—C22—C17 | 122.44 (17) | C26—S1—C27 | 93.26 (9) |
N3—C1—C2—C3 | −66.0 (3) | C28—C23—C24—N4 | −57.8 (2) |
C15—C1—C2—C3 | 176.9 (2) | O1—C23—C24—C25 | −172.68 (14) |
C16—C1—C2—C3 | 54.7 (3) | C28—C23—C24—C25 | 67.09 (19) |
N3—C1—C2—C7 | 116.51 (19) | O1—C23—C24—C16 | −60.63 (17) |
C15—C1—C2—C7 | −0.53 (19) | C28—C23—C24—C16 | 179.14 (14) |
C16—C1—C2—C7 | −122.75 (17) | N4—C24—C25—N3 | −158.22 (14) |
C7—C2—C3—C4 | −0.8 (3) | C16—C24—C25—N3 | −36.51 (16) |
C1—C2—C3—C4 | −178.1 (2) | C23—C24—C25—N3 | 78.75 (16) |
C2—C3—C4—C5 | 0.6 (4) | N4—C24—C25—C26 | −39.8 (2) |
C3—C4—C5—C6 | −1.4 (4) | C16—C24—C25—C26 | 81.88 (18) |
C4—C5—C6—C7 | 2.4 (4) | C23—C24—C25—C26 | −162.86 (16) |
C3—C2—C7—C6 | 1.8 (3) | N3—C25—C26—S1 | −39.77 (16) |
C1—C2—C7—C6 | 179.58 (19) | C24—C25—C26—S1 | −155.37 (13) |
C3—C2—C7—C8 | −178.23 (18) | O1—C23—C28—C29 | −37.1 (2) |
C1—C2—C7—C8 | −0.5 (2) | C24—C23—C28—C29 | 84.4 (2) |
C5—C6—C7—C2 | −2.6 (3) | O1—C23—C28—C37 | 141.13 (16) |
C5—C6—C7—C8 | 177.5 (2) | C24—C23—C28—C37 | −97.4 (2) |
C2—C7—C8—N2 | −177.9 (2) | C37—C28—C29—C30 | 0.0 (3) |
C6—C7—C8—N2 | 2.0 (4) | C23—C28—C29—C30 | 178.23 (18) |
C2—C7—C8—C15 | 1.4 (2) | C28—C29—C30—C31 | 1.2 (3) |
C6—C7—C8—C15 | −178.7 (2) | C29—C30—C31—C32 | −0.9 (3) |
N2—C9—C10—C11 | 178.4 (3) | C30—C31—C32—C33 | −179.1 (2) |
C14—C9—C10—C11 | 0.9 (4) | C30—C31—C32—C37 | −0.6 (3) |
C9—C10—C11—C12 | 0.3 (6) | C31—C32—C33—C34 | 178.2 (2) |
C10—C11—C12—C13 | −0.4 (6) | C37—C32—C33—C34 | −0.4 (3) |
C11—C12—C13—C14 | −0.7 (5) | C32—C33—C34—C35 | −0.9 (4) |
C12—C13—C14—N1 | −176.2 (3) | C33—C34—C35—C36 | 1.2 (4) |
C12—C13—C14—C9 | 1.8 (4) | C34—C35—C36—C37 | −0.4 (3) |
N2—C9—C14—N1 | −1.4 (3) | C35—C36—C37—C28 | −179.9 (2) |
C10—C9—C14—N1 | 176.1 (2) | C35—C36—C37—C32 | −0.9 (3) |
N2—C9—C14—C13 | −179.4 (2) | C29—C28—C37—C36 | 177.57 (18) |
C10—C9—C14—C13 | −1.9 (4) | C23—C28—C37—C36 | −0.6 (3) |
N2—C8—C15—N1 | −0.5 (3) | C29—C28—C37—C32 | −1.4 (3) |
C7—C8—C15—N1 | −179.83 (18) | C23—C28—C37—C32 | −179.62 (16) |
N2—C8—C15—C1 | 177.54 (18) | C31—C32—C37—C36 | −177.34 (18) |
C7—C8—C15—C1 | −1.8 (2) | C33—C32—C37—C36 | 1.3 (3) |
N3—C1—C15—N1 | 55.3 (2) | C31—C32—C37—C28 | 1.7 (3) |
C2—C1—C15—N1 | 179.41 (18) | C33—C32—C37—C28 | −179.68 (17) |
C16—C1—C15—N1 | −60.2 (2) | C8—C15—N1—C14 | 0.6 (3) |
N3—C1—C15—C8 | −122.67 (17) | C1—C15—N1—C14 | −177.19 (18) |
C2—C1—C15—C8 | 1.42 (19) | C13—C14—N1—C15 | 178.3 (2) |
C16—C1—C15—C8 | 121.85 (17) | C9—C14—N1—C15 | 0.3 (3) |
N3—C1—C16—C17 | −135.76 (16) | C15—C8—N2—C9 | −0.5 (3) |
C15—C1—C16—C17 | −17.7 (2) | C7—C8—N2—C9 | 178.7 (2) |
C2—C1—C16—C17 | 95.63 (19) | C10—C9—N2—C8 | −176.0 (2) |
N3—C1—C16—C24 | −10.06 (18) | C14—C9—N2—C8 | 1.4 (3) |
C15—C1—C16—C24 | 107.98 (17) | S1—C27—N3—C25 | −27.14 (18) |
C2—C1—C16—C24 | −138.67 (16) | S1—C27—N3—C1 | 105.11 (17) |
C24—C16—C17—C22 | −12.0 (3) | C26—C25—N3—C27 | 44.43 (19) |
C1—C16—C17—C22 | 109.8 (2) | C24—C25—N3—C27 | 169.30 (15) |
C24—C16—C17—C18 | 167.06 (17) | C26—C25—N3—C1 | −92.60 (17) |
C1—C16—C17—C18 | −71.1 (2) | C24—C25—N3—C1 | 32.28 (18) |
C22—C17—C18—C19 | −0.3 (3) | C15—C1—N3—C27 | 92.1 (2) |
C16—C17—C18—C19 | −179.3 (2) | C2—C1—N3—C27 | −20.4 (3) |
C17—C18—C19—C20 | 0.0 (4) | C16—C1—N3—C27 | −145.47 (17) |
C18—C19—C20—C21 | 0.6 (4) | C15—C1—N3—C25 | −136.36 (16) |
C19—C20—C21—C22 | −0.9 (4) | C2—C1—N3—C25 | 111.15 (18) |
C20—C21—C22—O1 | 178.0 (2) | C16—C1—N3—C25 | −13.90 (19) |
C20—C21—C22—C17 | 0.7 (4) | C25—C24—N4—O2 | 151.16 (16) |
C18—C17—C22—O1 | −177.23 (18) | C16—C24—N4—O2 | 35.0 (2) |
C16—C17—C22—O1 | 1.8 (3) | C23—C24—N4—O2 | −85.35 (19) |
C18—C17—C22—C21 | −0.1 (3) | C25—C24—N4—O3 | −31.9 (2) |
C16—C17—C22—C21 | 179.00 (19) | C16—C24—N4—O3 | −147.98 (16) |
C17—C16—C24—N4 | −81.57 (19) | C23—C24—N4—O3 | 91.63 (18) |
C1—C16—C24—N4 | 150.52 (15) | C21—C22—O1—C23 | 158.47 (18) |
C17—C16—C24—C25 | 156.62 (15) | C17—C22—O1—C23 | −24.2 (3) |
C1—C16—C24—C25 | 28.71 (18) | C28—C23—O1—C22 | 179.04 (16) |
C17—C16—C24—C23 | 39.69 (19) | C24—C23—O1—C22 | 53.8 (2) |
C1—C16—C24—C23 | −88.23 (16) | C25—C26—S1—C27 | 20.61 (14) |
O1—C23—C24—N4 | 62.48 (18) | N3—C27—S1—C26 | 2.64 (15) |
Cg1 is the centroid of the C9–C14 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C19—H19···S1i | 0.93 | 2.78 | 3.640 (3) | 156 |
C23—H23···N1 | 0.98 | 2.41 | 3.267 (3) | 145 |
C27—H27B···O2ii | 0.97 | 2.59 | 3.393 (3) | 140 |
C30—H30···O3iii | 0.93 | 2.57 | 3.480 (3) | 166 |
C33—H33···O3iv | 0.93 | 2.58 | 3.274 (3) | 131 |
C20—H20···Cg1v | 0.93 | 2.81 | 3.706 (3) | 163 |
Symmetry codes: (i) −x+1/2, y+1/2, −z+1/2; (ii) x−1, y, z; (iii) −x+1, −y, −z+1; (iv) −x, −y, −z+1; (v) x+1, y, z. |
C36H28N2O4 | F(000) = 2320 |
Mr = 552.60 | Dx = 1.184 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 35.7360 (5) Å | Cell parameters from 5464 reflections |
b = 11.4510 (4) Å | θ = 1.8–26.9° |
c = 15.3130 (3) Å | µ = 0.08 mm−1 |
β = 98.378 (2)° | T = 293 K |
V = 6199.4 (3) Å3 | Block, colourless |
Z = 8 | 0.30 × 0.24 × 0.22 mm |
Bruker Kappa APEXII CCD diffractometer | 4002 reflections with I > 2σ(I) |
ω and φ scans | Rint = 0.027 |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | θmax = 25.0°, θmin = 1.2° |
Tmin = 0.742, Tmax = 0.863 | h = −38→42 |
24488 measured reflections | k = −12→13 |
5464 independent reflections | l = −18→18 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.043 | w = 1/[σ2(Fo2) + (0.0521P)2 + 3.3964P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.126 | (Δ/σ)max < 0.001 |
S = 1.07 | Δρmax = 0.15 e Å−3 |
5464 reflections | Δρmin = −0.16 e Å−3 |
380 parameters | Extinction correction: SHELXL2018/3 (Sheldrick 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.00076 (10) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.11638 (5) | 0.06508 (18) | 0.21020 (13) | 0.0526 (5) | |
C2 | 0.08463 (6) | −0.01305 (19) | 0.17739 (14) | 0.0626 (6) | |
C3 | 0.05810 (7) | −0.0115 (3) | 0.10306 (19) | 0.0961 (9) | |
H3 | 0.057587 | 0.048710 | 0.062178 | 0.115* | |
C4 | 0.03208 (9) | −0.1019 (4) | 0.0903 (3) | 0.1207 (12) | |
H4 | 0.013886 | −0.101140 | 0.040225 | 0.145* | |
C5 | 0.03227 (8) | −0.1916 (3) | 0.1486 (3) | 0.1065 (11) | |
H5 | 0.014260 | −0.250396 | 0.137433 | 0.128* | |
C6 | 0.05926 (7) | −0.1975 (2) | 0.2259 (2) | 0.0786 (7) | |
C7 | 0.06434 (8) | −0.2845 (2) | 0.2910 (3) | 0.0942 (9) | |
H7 | 0.047848 | −0.347774 | 0.286966 | 0.113* | |
C8 | 0.09285 (9) | −0.2781 (2) | 0.3597 (2) | 0.0951 (9) | |
H8 | 0.095799 | −0.338284 | 0.400921 | 0.114* | |
C9 | 0.11834 (7) | −0.18250 (18) | 0.37060 (18) | 0.0755 (7) | |
H9 | 0.137421 | −0.178846 | 0.418798 | 0.091* | |
C10 | 0.11421 (6) | −0.09664 (16) | 0.30913 (14) | 0.0542 (5) | |
C11 | 0.08490 (5) | −0.10469 (17) | 0.23760 (15) | 0.0588 (5) | |
C12 | 0.13643 (5) | 0.01453 (15) | 0.30137 (12) | 0.0460 (4) | |
C13 | 0.18850 (6) | −0.06500 (19) | 0.22802 (14) | 0.0631 (6) | |
H13A | 0.180208 | −0.020888 | 0.174621 | 0.076* | |
H13B | 0.176720 | −0.141442 | 0.221732 | 0.076* | |
C14 | 0.23091 (6) | −0.0782 (2) | 0.24037 (14) | 0.0674 (6) | |
H14A | 0.238852 | −0.129872 | 0.289782 | 0.081* | |
H14B | 0.238469 | −0.113015 | 0.187899 | 0.081* | |
C15 | 0.24999 (6) | 0.0384 (2) | 0.25728 (14) | 0.0629 (6) | |
H15A | 0.243259 | 0.088851 | 0.206529 | 0.075* | |
H15B | 0.277228 | 0.028152 | 0.266245 | 0.075* | |
C16 | 0.23775 (5) | 0.09456 (17) | 0.33870 (12) | 0.0507 (5) | |
H16A | 0.245424 | 0.045909 | 0.390051 | 0.061* | |
H16B | 0.249717 | 0.170305 | 0.349153 | 0.061* | |
C17 | 0.19517 (5) | 0.10841 (14) | 0.32397 (11) | 0.0405 (4) | |
H17 | 0.188258 | 0.159896 | 0.273058 | 0.049* | |
C18 | 0.17508 (5) | 0.15277 (14) | 0.40030 (10) | 0.0388 (4) | |
C19 | 0.13489 (5) | 0.10116 (15) | 0.38040 (11) | 0.0435 (4) | |
H19 | 0.129935 | 0.055939 | 0.431831 | 0.052* | |
C20 | 0.10467 (5) | 0.19219 (17) | 0.36118 (12) | 0.0487 (5) | |
C21 | 0.06688 (6) | 0.1676 (2) | 0.36418 (15) | 0.0669 (6) | |
H21 | 0.059928 | 0.094245 | 0.382387 | 0.080* | |
C22 | 0.03949 (7) | 0.2515 (3) | 0.34024 (19) | 0.0896 (8) | |
H22 | 0.014138 | 0.234324 | 0.341579 | 0.108* | |
C23 | 0.04983 (8) | 0.3603 (3) | 0.3145 (2) | 0.0908 (8) | |
H23 | 0.031290 | 0.416307 | 0.298034 | 0.109* | |
C24 | 0.08670 (7) | 0.3874 (2) | 0.31264 (15) | 0.0703 (6) | |
H24 | 0.093426 | 0.461806 | 0.296162 | 0.084* | |
C25 | 0.11409 (6) | 0.30341 (17) | 0.33549 (12) | 0.0509 (5) | |
C26 | 0.17650 (5) | 0.28672 (14) | 0.40757 (11) | 0.0413 (4) | |
H26 | 0.202195 | 0.310881 | 0.400510 | 0.050* | |
C27 | 0.16712 (5) | 0.34448 (14) | 0.49082 (11) | 0.0415 (4) | |
C28 | 0.17669 (5) | 0.46539 (15) | 0.50394 (12) | 0.0450 (4) | |
C29 | 0.19530 (6) | 0.53161 (16) | 0.44563 (14) | 0.0567 (5) | |
H29 | 0.201503 | 0.496668 | 0.394821 | 0.068* | |
C30 | 0.20438 (7) | 0.64609 (18) | 0.46233 (17) | 0.0721 (6) | |
H30 | 0.216839 | 0.687805 | 0.423115 | 0.087* | |
C31 | 0.19517 (8) | 0.7009 (2) | 0.53741 (19) | 0.0803 (7) | |
H31 | 0.201638 | 0.778734 | 0.548245 | 0.096* | |
C32 | 0.17682 (7) | 0.64135 (19) | 0.59490 (17) | 0.0725 (7) | |
H32 | 0.170597 | 0.679086 | 0.644604 | 0.087* | |
C33 | 0.16703 (5) | 0.52252 (17) | 0.58021 (13) | 0.0540 (5) | |
C34 | 0.14859 (6) | 0.4597 (2) | 0.64003 (14) | 0.0643 (6) | |
H34 | 0.142673 | 0.496707 | 0.690319 | 0.077* | |
C35 | 0.13925 (6) | 0.3460 (2) | 0.62578 (14) | 0.0633 (6) | |
H35 | 0.126694 | 0.305819 | 0.665609 | 0.076* | |
C36 | 0.14858 (5) | 0.28885 (17) | 0.55064 (12) | 0.0522 (5) | |
H36 | 0.141920 | 0.210833 | 0.541431 | 0.063* | |
N1 | 0.17683 (4) | −0.00441 (12) | 0.30412 (9) | 0.0443 (4) | |
N2 | 0.19688 (4) | 0.10032 (13) | 0.48422 (9) | 0.0446 (4) | |
O1 | 0.12667 (4) | 0.14930 (13) | 0.17294 (9) | 0.0709 (4) | |
O2 | 0.22409 (4) | 0.15545 (12) | 0.51946 (8) | 0.0571 (4) | |
O3 | 0.18748 (4) | 0.00476 (11) | 0.50940 (9) | 0.0627 (4) | |
O4 | 0.15134 (4) | 0.33150 (10) | 0.33224 (8) | 0.0487 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0576 (12) | 0.0525 (11) | 0.0461 (11) | −0.0046 (9) | 0.0021 (9) | −0.0045 (9) |
C2 | 0.0584 (13) | 0.0660 (13) | 0.0601 (13) | −0.0069 (10) | −0.0020 (10) | −0.0108 (11) |
C3 | 0.0794 (17) | 0.114 (2) | 0.0852 (19) | −0.0180 (16) | −0.0215 (14) | −0.0094 (16) |
C4 | 0.091 (2) | 0.142 (3) | 0.117 (3) | −0.032 (2) | −0.0279 (19) | −0.026 (2) |
C5 | 0.0661 (17) | 0.105 (2) | 0.143 (3) | −0.0336 (16) | −0.0011 (19) | −0.044 (2) |
C6 | 0.0606 (14) | 0.0592 (14) | 0.119 (2) | −0.0139 (11) | 0.0230 (15) | −0.0269 (15) |
C7 | 0.0746 (18) | 0.0551 (15) | 0.160 (3) | −0.0212 (13) | 0.0402 (19) | −0.0172 (18) |
C8 | 0.106 (2) | 0.0475 (14) | 0.138 (3) | −0.0099 (14) | 0.037 (2) | 0.0152 (15) |
C9 | 0.0815 (16) | 0.0490 (12) | 0.0959 (18) | −0.0076 (11) | 0.0127 (13) | 0.0128 (12) |
C10 | 0.0586 (12) | 0.0402 (10) | 0.0649 (13) | −0.0048 (9) | 0.0127 (10) | −0.0030 (9) |
C11 | 0.0490 (11) | 0.0521 (12) | 0.0761 (14) | −0.0082 (9) | 0.0121 (10) | −0.0218 (11) |
C12 | 0.0542 (11) | 0.0382 (9) | 0.0442 (10) | −0.0071 (8) | 0.0031 (8) | −0.0002 (8) |
C13 | 0.0747 (14) | 0.0630 (13) | 0.0510 (12) | −0.0012 (11) | 0.0066 (10) | −0.0232 (10) |
C14 | 0.0704 (14) | 0.0788 (15) | 0.0544 (12) | 0.0128 (12) | 0.0134 (11) | −0.0214 (11) |
C15 | 0.0594 (12) | 0.0819 (15) | 0.0490 (11) | 0.0065 (11) | 0.0135 (9) | −0.0075 (11) |
C16 | 0.0515 (11) | 0.0555 (11) | 0.0457 (10) | −0.0018 (9) | 0.0096 (8) | −0.0066 (9) |
C17 | 0.0497 (10) | 0.0397 (9) | 0.0320 (8) | −0.0028 (8) | 0.0053 (7) | −0.0003 (7) |
C18 | 0.0494 (10) | 0.0364 (9) | 0.0304 (8) | 0.0001 (7) | 0.0054 (7) | 0.0016 (7) |
C19 | 0.0505 (10) | 0.0409 (9) | 0.0399 (9) | −0.0043 (8) | 0.0096 (8) | 0.0022 (8) |
C20 | 0.0476 (11) | 0.0550 (11) | 0.0435 (10) | 0.0018 (9) | 0.0062 (8) | −0.0027 (9) |
C21 | 0.0538 (13) | 0.0753 (15) | 0.0722 (14) | −0.0007 (11) | 0.0108 (11) | −0.0047 (12) |
C22 | 0.0497 (13) | 0.113 (2) | 0.105 (2) | 0.0131 (14) | 0.0077 (13) | −0.0040 (18) |
C23 | 0.0709 (18) | 0.090 (2) | 0.108 (2) | 0.0287 (15) | 0.0020 (15) | 0.0058 (17) |
C24 | 0.0750 (16) | 0.0622 (13) | 0.0709 (15) | 0.0183 (12) | 0.0017 (12) | 0.0036 (11) |
C25 | 0.0569 (12) | 0.0527 (11) | 0.0420 (10) | 0.0078 (9) | 0.0037 (9) | −0.0003 (9) |
C26 | 0.0485 (10) | 0.0374 (9) | 0.0385 (9) | −0.0019 (8) | 0.0075 (8) | 0.0025 (7) |
C27 | 0.0442 (10) | 0.0399 (9) | 0.0406 (9) | 0.0026 (7) | 0.0064 (8) | −0.0017 (8) |
C28 | 0.0449 (10) | 0.0399 (10) | 0.0486 (10) | 0.0050 (8) | 0.0018 (8) | −0.0051 (8) |
C29 | 0.0663 (13) | 0.0409 (10) | 0.0635 (13) | −0.0014 (9) | 0.0117 (10) | −0.0022 (9) |
C30 | 0.0810 (16) | 0.0437 (12) | 0.0903 (17) | −0.0069 (11) | 0.0079 (13) | 0.0020 (12) |
C31 | 0.0918 (18) | 0.0391 (12) | 0.104 (2) | 0.0025 (11) | −0.0069 (15) | −0.0148 (13) |
C32 | 0.0802 (16) | 0.0533 (13) | 0.0797 (16) | 0.0144 (12) | −0.0028 (13) | −0.0254 (12) |
C33 | 0.0525 (11) | 0.0490 (11) | 0.0578 (12) | 0.0125 (9) | −0.0005 (9) | −0.0120 (9) |
C34 | 0.0679 (14) | 0.0736 (15) | 0.0543 (12) | 0.0145 (11) | 0.0183 (11) | −0.0170 (11) |
C35 | 0.0673 (13) | 0.0734 (15) | 0.0537 (12) | 0.0045 (11) | 0.0240 (10) | −0.0015 (11) |
C36 | 0.0613 (12) | 0.0479 (11) | 0.0494 (11) | 0.0010 (9) | 0.0142 (9) | −0.0020 (9) |
N1 | 0.0514 (9) | 0.0416 (8) | 0.0400 (8) | −0.0027 (7) | 0.0073 (7) | −0.0072 (6) |
N2 | 0.0598 (10) | 0.0397 (8) | 0.0342 (8) | 0.0023 (7) | 0.0069 (7) | −0.0012 (7) |
O1 | 0.0850 (10) | 0.0700 (10) | 0.0530 (8) | −0.0173 (8) | −0.0057 (7) | 0.0154 (8) |
O2 | 0.0614 (8) | 0.0619 (9) | 0.0445 (7) | −0.0041 (7) | −0.0042 (6) | −0.0052 (6) |
O3 | 0.0911 (10) | 0.0452 (8) | 0.0497 (8) | −0.0023 (7) | 0.0028 (7) | 0.0117 (6) |
O4 | 0.0599 (8) | 0.0432 (7) | 0.0428 (7) | 0.0028 (6) | 0.0073 (6) | 0.0067 (5) |
C1—O1 | 1.205 (2) | C18—N2 | 1.526 (2) |
C1—C2 | 1.474 (3) | C18—C26 | 1.538 (2) |
C1—C12 | 1.583 (3) | C18—C19 | 1.542 (2) |
C2—C3 | 1.371 (3) | C19—C20 | 1.499 (3) |
C2—C11 | 1.396 (3) | C19—H19 | 0.9800 |
C3—C4 | 1.386 (4) | C20—C21 | 1.387 (3) |
C3—H3 | 0.9300 | C20—C25 | 1.389 (3) |
C4—C5 | 1.361 (5) | C21—C22 | 1.382 (3) |
C4—H4 | 0.9300 | C21—H21 | 0.9300 |
C5—C6 | 1.416 (4) | C22—C23 | 1.374 (4) |
C5—H5 | 0.9300 | C22—H22 | 0.9300 |
C6—C11 | 1.398 (3) | C23—C24 | 1.358 (4) |
C6—C7 | 1.402 (4) | C23—H23 | 0.9300 |
C7—C8 | 1.356 (4) | C24—C25 | 1.381 (3) |
C7—H7 | 0.9300 | C24—H24 | 0.9300 |
C8—C9 | 1.419 (3) | C25—O4 | 1.377 (2) |
C8—H8 | 0.9300 | C26—O4 | 1.449 (2) |
C9—C10 | 1.354 (3) | C26—C27 | 1.516 (2) |
C9—H9 | 0.9300 | C26—H26 | 0.9800 |
C10—C11 | 1.404 (3) | C27—C36 | 1.364 (3) |
C10—C12 | 1.514 (2) | C27—C28 | 1.433 (2) |
C12—N1 | 1.454 (2) | C28—C29 | 1.410 (3) |
C12—C19 | 1.572 (2) | C28—C33 | 1.424 (3) |
C13—N1 | 1.468 (2) | C29—C30 | 1.366 (3) |
C13—C14 | 1.507 (3) | C29—H29 | 0.9300 |
C13—H13A | 0.9700 | C30—C31 | 1.391 (4) |
C13—H13B | 0.9700 | C30—H30 | 0.9300 |
C14—C15 | 1.504 (3) | C31—C32 | 1.356 (4) |
C14—H14A | 0.9700 | C31—H31 | 0.9300 |
C14—H14B | 0.9700 | C32—C33 | 1.415 (3) |
C15—C16 | 1.523 (3) | C32—H32 | 0.9300 |
C15—H15A | 0.9700 | C33—C34 | 1.403 (3) |
C15—H15B | 0.9700 | C34—C35 | 1.353 (3) |
C16—C17 | 1.514 (2) | C34—H34 | 0.9300 |
C16—H16A | 0.9700 | C35—C36 | 1.405 (3) |
C16—H16B | 0.9700 | C35—H35 | 0.9300 |
C17—N1 | 1.461 (2) | C36—H36 | 0.9300 |
C17—C18 | 1.544 (2) | N2—O2 | 1.2174 (18) |
C17—H17 | 0.9800 | N2—O3 | 1.2233 (18) |
O1—C1—C2 | 126.65 (19) | C26—C18—C19 | 114.61 (14) |
O1—C1—C12 | 125.46 (17) | N2—C18—C17 | 105.74 (13) |
C2—C1—C12 | 107.79 (17) | C26—C18—C17 | 111.64 (13) |
C3—C2—C11 | 119.7 (2) | C19—C18—C17 | 104.29 (13) |
C3—C2—C1 | 132.8 (2) | C20—C19—C18 | 113.32 (14) |
C11—C2—C1 | 107.47 (17) | C20—C19—C12 | 113.13 (14) |
C2—C3—C4 | 118.5 (3) | C18—C19—C12 | 104.94 (13) |
C2—C3—H3 | 120.8 | C20—C19—H19 | 108.4 |
C4—C3—H3 | 120.8 | C18—C19—H19 | 108.4 |
C5—C4—C3 | 122.1 (3) | C12—C19—H19 | 108.4 |
C5—C4—H4 | 118.9 | C21—C20—C25 | 118.24 (18) |
C3—C4—H4 | 118.9 | C21—C20—C19 | 121.96 (18) |
C4—C5—C6 | 121.5 (3) | C25—C20—C19 | 119.73 (16) |
C4—C5—H5 | 119.2 | C22—C21—C20 | 120.4 (2) |
C6—C5—H5 | 119.2 | C22—C21—H21 | 119.8 |
C11—C6—C7 | 115.8 (2) | C20—C21—H21 | 119.8 |
C11—C6—C5 | 115.1 (3) | C23—C22—C21 | 119.8 (2) |
C7—C6—C5 | 129.1 (3) | C23—C22—H22 | 120.1 |
C8—C7—C6 | 121.2 (2) | C21—C22—H22 | 120.1 |
C8—C7—H7 | 119.4 | C24—C23—C22 | 121.0 (2) |
C6—C7—H7 | 119.4 | C24—C23—H23 | 119.5 |
C7—C8—C9 | 122.0 (3) | C22—C23—H23 | 119.5 |
C7—C8—H8 | 119.0 | C23—C24—C25 | 119.3 (2) |
C9—C8—H8 | 119.0 | C23—C24—H24 | 120.3 |
C10—C9—C8 | 118.4 (3) | C25—C24—H24 | 120.3 |
C10—C9—H9 | 120.8 | O4—C25—C24 | 118.78 (18) |
C8—C9—H9 | 120.8 | O4—C25—C20 | 119.99 (16) |
C9—C10—C11 | 119.21 (19) | C24—C25—C20 | 121.2 (2) |
C9—C10—C12 | 131.26 (19) | O4—C26—C27 | 109.11 (13) |
C11—C10—C12 | 109.53 (17) | O4—C26—C18 | 106.57 (13) |
C2—C11—C6 | 123.1 (2) | C27—C26—C18 | 119.13 (14) |
C2—C11—C10 | 113.48 (17) | O4—C26—H26 | 107.2 |
C6—C11—C10 | 123.4 (2) | C27—C26—H26 | 107.2 |
N1—C12—C10 | 113.71 (15) | C18—C26—H26 | 107.2 |
N1—C12—C19 | 102.58 (13) | C36—C27—C28 | 119.11 (16) |
C10—C12—C19 | 113.12 (15) | C36—C27—C26 | 123.32 (16) |
N1—C12—C1 | 113.58 (15) | C28—C27—C26 | 117.49 (15) |
C10—C12—C1 | 101.61 (15) | C29—C28—C33 | 117.74 (17) |
C19—C12—C1 | 112.70 (14) | C29—C28—C27 | 123.77 (17) |
N1—C13—C14 | 110.15 (16) | C33—C28—C27 | 118.49 (17) |
N1—C13—H13A | 109.6 | C30—C29—C28 | 121.3 (2) |
C14—C13—H13A | 109.6 | C30—C29—H29 | 119.4 |
N1—C13—H13B | 109.6 | C28—C29—H29 | 119.4 |
C14—C13—H13B | 109.6 | C29—C30—C31 | 120.6 (2) |
H13A—C13—H13B | 108.1 | C29—C30—H30 | 119.7 |
C15—C14—C13 | 110.80 (18) | C31—C30—H30 | 119.7 |
C15—C14—H14A | 109.5 | C32—C31—C30 | 120.3 (2) |
C13—C14—H14A | 109.5 | C32—C31—H31 | 119.8 |
C15—C14—H14B | 109.5 | C30—C31—H31 | 119.8 |
C13—C14—H14B | 109.5 | C31—C32—C33 | 120.8 (2) |
H14A—C14—H14B | 108.1 | C31—C32—H32 | 119.6 |
C14—C15—C16 | 109.79 (17) | C33—C32—H32 | 119.6 |
C14—C15—H15A | 109.7 | C34—C33—C32 | 121.2 (2) |
C16—C15—H15A | 109.7 | C34—C33—C28 | 119.54 (18) |
C14—C15—H15B | 109.7 | C32—C33—C28 | 119.2 (2) |
C16—C15—H15B | 109.7 | C35—C34—C33 | 121.09 (19) |
H15A—C15—H15B | 108.2 | C35—C34—H34 | 119.5 |
C17—C16—C15 | 108.95 (15) | C33—C34—H34 | 119.5 |
C17—C16—H16A | 109.9 | C34—C35—C36 | 119.8 (2) |
C15—C16—H16A | 109.9 | C34—C35—H35 | 120.1 |
C17—C16—H16B | 109.9 | C36—C35—H35 | 120.1 |
C15—C16—H16B | 109.9 | C27—C36—C35 | 121.92 (18) |
H16A—C16—H16B | 108.3 | C27—C36—H36 | 119.0 |
N1—C17—C16 | 110.45 (14) | C35—C36—H36 | 119.0 |
N1—C17—C18 | 101.79 (13) | C12—N1—C17 | 106.72 (13) |
C16—C17—C18 | 119.33 (14) | C12—N1—C13 | 116.30 (14) |
N1—C17—H17 | 108.2 | C17—N1—C13 | 114.36 (15) |
C16—C17—H17 | 108.2 | O2—N2—O3 | 124.22 (15) |
C18—C17—H17 | 108.2 | O2—N2—C18 | 116.50 (14) |
N2—C18—C26 | 108.91 (13) | O3—N2—C18 | 119.18 (14) |
N2—C18—C19 | 111.24 (13) | C25—O4—C26 | 112.30 (13) |
O1—C1—C2—C3 | −3.4 (4) | C12—C19—C20—C25 | −99.28 (19) |
C12—C1—C2—C3 | 179.9 (3) | C25—C20—C21—C22 | 1.4 (3) |
O1—C1—C2—C11 | 174.7 (2) | C19—C20—C21—C22 | −175.6 (2) |
C12—C1—C2—C11 | −2.0 (2) | C20—C21—C22—C23 | −0.9 (4) |
C11—C2—C3—C4 | 0.2 (4) | C21—C22—C23—C24 | −0.5 (4) |
C1—C2—C3—C4 | 178.2 (3) | C22—C23—C24—C25 | 1.2 (4) |
C2—C3—C4—C5 | −0.4 (5) | C23—C24—C25—O4 | 179.1 (2) |
C3—C4—C5—C6 | 0.0 (6) | C23—C24—C25—C20 | −0.7 (3) |
C4—C5—C6—C11 | 0.7 (4) | C21—C20—C25—O4 | 179.57 (17) |
C4—C5—C6—C7 | −177.7 (3) | C19—C20—C25—O4 | −3.4 (3) |
C11—C6—C7—C8 | −0.9 (4) | C21—C20—C25—C24 | −0.6 (3) |
C5—C6—C7—C8 | 177.4 (3) | C19—C20—C25—C24 | 176.42 (18) |
C6—C7—C8—C9 | 1.6 (4) | N2—C18—C26—O4 | −172.49 (12) |
C7—C8—C9—C10 | −1.3 (4) | C19—C18—C26—O4 | −47.16 (18) |
C8—C9—C10—C11 | 0.5 (3) | C17—C18—C26—O4 | 71.12 (17) |
C8—C9—C10—C12 | −179.6 (2) | N2—C18—C26—C27 | −48.6 (2) |
C3—C2—C11—C6 | 0.5 (3) | C19—C18—C26—C27 | 76.68 (19) |
C1—C2—C11—C6 | −177.97 (19) | C17—C18—C26—C27 | −165.04 (14) |
C3—C2—C11—C10 | 178.3 (2) | O4—C26—C27—C36 | 105.74 (18) |
C1—C2—C11—C10 | −0.2 (2) | C18—C26—C27—C36 | −16.9 (2) |
C7—C6—C11—C2 | 177.7 (2) | O4—C26—C27—C28 | −70.94 (18) |
C5—C6—C11—C2 | −0.9 (3) | C18—C26—C27—C28 | 166.47 (15) |
C7—C6—C11—C10 | 0.1 (3) | C36—C27—C28—C29 | −179.01 (18) |
C5—C6—C11—C10 | −178.5 (2) | C26—C27—C28—C29 | −2.2 (3) |
C9—C10—C11—C2 | −177.7 (2) | C36—C27—C28—C33 | 1.1 (2) |
C12—C10—C11—C2 | 2.3 (2) | C26—C27—C28—C33 | 177.96 (15) |
C9—C10—C11—C6 | 0.1 (3) | C33—C28—C29—C30 | 1.1 (3) |
C12—C10—C11—C6 | −179.87 (19) | C27—C28—C29—C30 | −178.72 (19) |
C9—C10—C12—N1 | 54.4 (3) | C28—C29—C30—C31 | −0.5 (3) |
C11—C10—C12—N1 | −125.65 (17) | C29—C30—C31—C32 | −0.4 (4) |
C9—C10—C12—C19 | −62.1 (3) | C30—C31—C32—C33 | 0.6 (4) |
C11—C10—C12—C19 | 117.85 (17) | C31—C32—C33—C34 | 179.0 (2) |
C9—C10—C12—C1 | 176.8 (2) | C31—C32—C33—C28 | 0.0 (3) |
C11—C10—C12—C1 | −3.2 (2) | C29—C28—C33—C34 | −179.83 (18) |
O1—C1—C12—N1 | −51.1 (3) | C27—C28—C33—C34 | 0.0 (3) |
C2—C1—C12—N1 | 125.63 (17) | C29—C28—C33—C32 | −0.9 (3) |
O1—C1—C12—C10 | −173.6 (2) | C27—C28—C33—C32 | 178.98 (17) |
C2—C1—C12—C10 | 3.1 (2) | C32—C33—C34—C35 | 180.0 (2) |
O1—C1—C12—C19 | 65.0 (3) | C28—C33—C34—C35 | −1.1 (3) |
C2—C1—C12—C19 | −118.25 (17) | C33—C34—C35—C36 | 0.9 (3) |
N1—C13—C14—C15 | −54.9 (2) | C28—C27—C36—C35 | −1.3 (3) |
C13—C14—C15—C16 | 58.2 (2) | C26—C27—C36—C35 | −177.94 (17) |
C14—C15—C16—C17 | −58.6 (2) | C34—C35—C36—C27 | 0.3 (3) |
C15—C16—C17—N1 | 56.9 (2) | C10—C12—N1—C17 | −162.50 (15) |
C15—C16—C17—C18 | 174.30 (16) | C19—C12—N1—C17 | −40.00 (16) |
N1—C17—C18—N2 | 85.76 (14) | C1—C12—N1—C17 | 81.93 (17) |
C16—C17—C18—N2 | −36.02 (19) | C10—C12—N1—C13 | 68.5 (2) |
N1—C17—C18—C26 | −155.94 (13) | C19—C12—N1—C13 | −168.96 (15) |
C16—C17—C18—C26 | 82.28 (19) | C1—C12—N1—C13 | −47.0 (2) |
N1—C17—C18—C19 | −31.64 (15) | C16—C17—N1—C12 | 173.41 (14) |
C16—C17—C18—C19 | −153.42 (15) | C18—C17—N1—C12 | 45.67 (16) |
N2—C18—C19—C20 | 130.92 (15) | C16—C17—N1—C13 | −56.51 (19) |
C26—C18—C19—C20 | 6.8 (2) | C18—C17—N1—C13 | 175.76 (15) |
C17—C18—C19—C20 | −115.54 (15) | C14—C13—N1—C12 | −179.97 (17) |
N2—C18—C19—C12 | −105.17 (14) | C14—C13—N1—C17 | 54.9 (2) |
C26—C18—C19—C12 | 130.73 (14) | C26—C18—N2—O2 | −33.06 (19) |
C17—C18—C19—C12 | 8.37 (16) | C19—C18—N2—O2 | −160.32 (14) |
N1—C12—C19—C20 | 142.03 (15) | C17—C18—N2—O2 | 87.05 (16) |
C10—C12—C19—C20 | −95.07 (18) | C26—C18—N2—O3 | 150.48 (15) |
C1—C12—C19—C20 | 19.5 (2) | C19—C18—N2—O3 | 23.2 (2) |
N1—C12—C19—C18 | 18.00 (16) | C17—C18—N2—O3 | −89.41 (17) |
C10—C12—C19—C18 | 140.90 (15) | C24—C25—O4—C26 | 137.77 (17) |
C1—C12—C19—C18 | −104.52 (16) | C20—C25—O4—C26 | −42.4 (2) |
C18—C19—C20—C21 | −163.06 (17) | C27—C26—O4—C25 | −63.81 (17) |
C12—C19—C20—C21 | 77.6 (2) | C18—C26—O4—C25 | 66.03 (17) |
C18—C19—C20—C25 | 20.0 (2) |
Cg1 is the centroid of the C6–C11 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13A···O3i | 0.97 | 2.59 | 3.413 (3) | 143 |
C17—H17···O1 | 0.98 | 2.50 | 3.148 (2) | 124 |
C32—H32···O1ii | 0.93 | 2.59 | 3.318 (3) | 135 |
C35—H35···Cg1iii | 0.93 | 2.92 | 3.849 (2) | 176 |
Symmetry codes: (i) x, −y, z−1/2; (ii) x, −y+1, z+1/2; (iii) x, −y, z+1/2. |
Acknowledgements
The authors are grateful to the SAIF, IIT, Madras, India, for the data collection.
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