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Three-component reaction between isatoic anhydride, amine and methyl-substituted furylacrylaldehydes: crystal structures of 3-benzyl-2-[(E)-2-(5-methylfuran-2-yl)vinyl]-2,3-dihydroquinazolin-4(1H)-one, 3-benzyl-2-[(E)-2-(furan-2-yl)-1-methylvinyl]-2,3-dihydroquinazolin-4(1H)-one and 3-(furan-2-ylmethyl)-2-[(E)-2-(furan-2-yl)-1-methylvinyl]-2,3-dihydroquinazolin-4(1H)-one
aOrganic Chemistry Department, Peoples' Friendship University of Russia (RUDN University), 6 Miklukho-Maklay St., Moscow 117198, Russian Federation, bDepartment of Chemistry, Faculty of Sciences, University of Douala, PO Box 24157, Douala, Republic of , Cameroon, cDepartment of Chemistry, Goa University, Taleigao Plateau, Goa 403 206, India, dNational Research Centre "Kurchatov Institute", 1 Acad. Kurchatov Sq., Moscow 123182, Russian Federation, and eInorganic Chemistry Department, Peoples' Friendship University of Russia (RUDN University), 6 Miklukho-Maklay St., Moscow 117198, Russian Federation
*Correspondence e-mail: toflavien@yahoo.fr, vnkhrustalev@gmail.com
Compounds (I), C22H20N2O2, (II), C22H20N2O2 and (III), C20H18N2O3 are the products of three-component reactions between isatoic anhydride, the corresponding amine and 3-(5-methylfuran-2-yl)- or (furan-2-yl)-2-methylacrylaldehyde. Compound (I) crystallizes in the monoclinic P21/n, while compounds (II) and (III) are isostructural and crystallize in the orthorhombic Pbca. The tetrahydropyrimidine ring in (I)–(III) adopts a sofa conformation. The NH nitrogen atom has a trigonal–pyramidal geometry, whereas the N(R) nitrogen atom is flattened. The furyl-vinyl substituents in (I)–(III) are practically planar and have an E configuration at the C=C double bond. In (I), this bulky fragment occupies the axial position at the quaternary carbon atom of the tetrahydropyrimidine ring, whereas in (II) and (III) it is equatorially disposed. In the crystal of (I), molecules form hydrogen-bonded chains propagating along [001] by strong intermolecular N—H⋯O hydrogen bonds. The chains are packed in stacks along the a-axis direction. In the crystals of (II) and (III), molecules also form hydrogen-bonded chains propagating along [100] by strong intermolecular N—H⋯O hydrogen bonds. However, despite the fact that compounds (II) and (III) are isostructural, steric differences between the phenyl and furyl substituents result in chains with different geometries. Thus in the crystal of (II) the chains have a zigzag-like structure, whereas in the crystal of (III), they are almost linear. In both (II) and (III), the hydrogen-bonded chains are further packed in stacks along the b-axis direction.
1. Chemical context
3-Aryl- and 3-hetaryl-substituted allylamines and allylic et al., 2016; Celltech R&D Ltd, 2004
).
As depicted in Fig. 1, these substances most often undergo an N-acylation reaction with unsaturated or acyl chlorides to trigger the subsequent intramolecular Diels–Alder As a result, this sequence gives functionalized two- or three-membered heterocycles. A wide range of dienes (Tomberg et al., 2015
; Magedov et al., 2012
; Slauson et al., 2015
; Sun et al., 2000
), (Hu et al., 2010
; Sun et al., 2000
; Yamazaki et al., 2016
; Kocsis et al., 2015
) and various heterocycles (Lu et al., 2005
; Kim et al., 2014
; He et al., 2011
) can be applied in this transformation.
![]() | Figure 1 One of the synthetic pathways for the exploration of 3-substituted allylamines and allylic alcohols. |
Until now, only one example of the synthesis of 3-(furyl)allylamines linked to a quinazoline fragment has been described in literature (Zaytsev et al., 2015). 2-Vinylfurylquinazolinones containing no methyl groups were obtained by a three-component reaction between isatoic anhydride, a primary amine, and furylacrolein. Some further transformation of these quinazolinones has been demonstrated.
This communication pursues the aim of acquiring structural information about 2-vinylfurylquinazolinones bearing a methyl group on the furan ring or at the double bond of the allylamine fragment, with the aim of further elucidating all aspects of its interaction with α,β-unsaturated acid anhydrides.
2. Structural commentary
Compounds (I), C22H20N2O2, (II)
, C22H20N2O2 and (III)
, C20H18N2O3 (Figs. 2
–4
) are the products of three-component reactions between isatoic anhydride, the corresponding amine and 3-(5-methylfuran-2-yl)- or (furan-2-yl)-2-methylacrylaldehyde. Compound (I)
crystallizes in the monoclinic P21/n, while compounds (II)
and (III)
are isostructural and crystallize in the orthorhombic Pbca.
![]() | Figure 2 Molecular structure of (I) ![]() |
![]() | Figure 3 Molecular structure of (II) ![]() |
![]() | Figure 4 Molecular structure of (III) ![]() |
The tetrahydropyrimidine ring in (I)–(III) adopts a sofa conformation, with the C2 carbon atom deviating from the mean plane of the other atoms of the ring by 0.639 (2), 0.476 (3) and 0.465 (3) Å, respectively. The nitrogen atom N1 has a trigonal–pyramidal geometry [the sums of the bond angles are 345, 348 and 350° for (I)–(III), respectively], whereas the nitrogen atom N3 is flattened [the sums of the bond angles are 357.3, 356.2 and 356.8° for (I)–(III), respectively]. The furyl-vinyl substituents in (I)–(III) are practically planar and have an E configuration at the C9=C10 double bond. Interestingly, in (I) this bulky fragment occupies the axial position at the quaternary C2 carbon atom of the tetrahydropyrimidine ring, whereas in (II)
and (III)
it is equatorially disposed. Apparently, this may be explained by the different directions of the three-component reactions.
The molecules of (I)–(III) possess an asymmetric center at the C2 carbon atom. The crystals of (I)–(III) are racemates.
3. Supramolecular features
In the crystal of (I), molecules form infinite hydrogen-bonded chains propagating along [001] by strong intermolecular N1—H1⋯O2i hydrogen bonds (Table 1
, Fig. 5
). Neighboring molecules within the chains are rotated by 180° relative to each other. The chains are packed in stacks along the a-axis direction (Fig. 5
).
|
![]() | Figure 5 Crystal structure of (I) ![]() |
In the crystals of (II) and (III)
, molecules also form infinite hydrogen-bonded chains propagating along [100] by strong intermolecular N1—H1⋯O2i (Table 2
, Fig. 6
) and N1—H1⋯O3i (Table 3
, Fig. 7
) hydrogen bonds, respectively, with neighboring molecules rotated by 180° relative to each other. However, despite the fact that compounds (II)
and (III)
are isostructural, steric differences between the phenyl and furyl substituents result in chains with different geometries. Thus, in the crystal of (II)
the chains have a zigzag-like structure (Fig. 6
), whereas in the crystal of (III)
they are almost linear (Fig. 7
). In both (II)
and (III)
, the hydrogen-bonded chains are further packed in stacks along the b-axis direction (Figs. 6
and 7
).
|
|
![]() | Figure 6 Crystal structure of (II) ![]() |
![]() | Figure 7 Crystal structure of (III) ![]() |
4. Synthesis and crystallization
3-Arylmethyl-2-[(E)-2-(furan-2-yl)vinyl]-2,3-dihydroquinazolin-4-ones (I)–(III) were synthesized using a method similar to the recently described procedure (Zaytsev et al., 2017).
General procedure. p-TsOH (0.79 g, 4.6 mmol) was added to a mixture of isatoic anhydride (1.5 g, 9.2 mmol), corresponding amine (11.0 mmol), and 3-(5-methylfuran-2-yl)- or (furan-2-yl)-2-methylacrylaldehyde (9.2 mmol) in EtOH (50 mL) (Fig. 8). The reaction mixture was heated under reflux for 4 h. The progress of the reaction was monitored by TLC. When the reaction was complete, the mixture was diluted with H2O (100 mL) and extracted with EtOAc (3×50 mL). The organic layers were combined, dried (MgSO4), concentrated in vacuo and the residue was purified by (3×20 cm) on SiO2 using hexane and then EtOAc/hexane (1/10→1/5) mixtures as The resulting product was recrystallized from a mixture hexane–EtOAc to afford analytically pure samples of the target products.
![]() | Figure 8 Synthesis of (I)–(III) by the three-component reaction between isatoic anhydride, the corresponding amine and 3-(5-methylfuran-2-yl)- or (furan-2-yl)-2-methylacrylaldehyde. |
3-Benzyl-2-[(E)-2-(5-methylfuran-2-yl)vinyl]-2,3-dihydroquinazolin-4(1H)-one (I). Colourless needles, yield 0.7 g (22%), m.p. 430.1–432.1 K. IR (KBr), ν (cm−1): 3272, 1632, 1611. 1H NMR (CDCl3, 400 MHz, 301 K): δ = 2.25 (s, 3H, CH3), 3.86 (d, 1H, CH2—N, J = 15.1), 4.34 (br s, 1H, NH), 4.97 (dd, 1H, H2, J = 3.2, J = 4.6), 5.63 (d, 1H, CH2—N, J = 15.1), 5.95 (dd, 1H, H4, furyl, J = 0.9, J = 3.2), 6.15–6.20 (m, 2H, –CH=CH–, H3, furyl), 6.59 (d, 1H, H8, J = 7.8), 6.87 (br t, 1H, H6, J = 7.8), 7.27–7.34 (m, 7H, HAr, –CH=CH–), 7.99 (dd, 1H, H5, J = 1.4, J = 7.8). 13C NMR (CDCl3, 150.9 MHz, 301 K): δ = 13.8 (CH3), 46.6 (CH2–N), 70.1 (C2), 107.8, 111.4, 114.8, 115.8, 119.3, 121.5, 121.8, 127.6, 128.1, 128.8, 128.9, 133.6, 137.1, 145.4, 149.6, 153.1 (CAr, –CH=CH–), 162.9 (NCO). MS (EI, 70 eV): m/z = 344 [M]+ (2), 251 (16), 209 (14), 104 (10), 91 (100), 77 (20), 65 (27), 43 (24).
3-Benzyl-2-[(E)-2-(furan-2-yl)-1-methylvinyl]-2,3-dihydroquinazolin-4(1H)-one (II). Colourless plates, yield 0.95 g (30%), m.p. 405.1–406.1 K. IR (KBr), ν (cm−1): 3294, 1630. 1H NMR (CDCl3, 400 MHz, 301 K): δ = 1.96 (s, 3H, CH3), 3.77 (d, 1H, CH2—N, J = 15.1), 4.36 (br s, 1H, NH), 5.12 (br s, 1H, H2), 5.63 (d, 1H, CH2—N, J = 15.1), 6.11 (s, 1H, –C=CH–), 6.31 (d, 1H, H3, furyl, J = 3.2), 6.41 (dd, 1H, H4, furyl, J = 1.8, J = 3.2), 6.51 (d, 1H, H8, J = 7.8), 6.78 (t, 1H, H6, J = 7.8), 7.21–7.31 (m, 6H, HAr), 7.41 (br d, 1H, H5, furyl, J = 1.8), 7.94 (dd, 1H, H5, J = 1.4, J = 7.8). 13C NMR (CDCl3, 150.9 MHz, 301 K): δ = 13.6 (CH3), 46.5 (CH2—N), 75.1 (C2), 111.0, 111.5, 113.6, 114.4, 117.4, 118.6, 127.6, 128.2, 128.7, 128.8, 133.6, 133.8, 136.9, 142.3, 145.7, 151.8 (CAr, –C=CH–), 163.0 (NCO). MS (EI, 70 eV): m/z = 344 [M]+ (4), 237 (55), 207 (14), 167 (5), 91 (100), 77 (19), 65 (11), 44 (8).
3-(2-Furylmethyl)-2-[(E)-2-(furan-2-yl)-1-methylvinyl]-2,3-dihydroquinazolin-4(1H)-one (III). Yellow plates, yield 0.83 g (27%), m.p. 380.1–381.1 K (hexane–EtOAc). IR (KBr), ν (cm−1): 3308, 1632. 1H NMR (CDCl3, 400 MHz, 301 K): δ = 1.99 (s, 3H, CH3), 3.93 (d, 1H, CH2—N, J = 15.4), 4.22 (br s, 1H, NH), 5.32 (br s, 1H, H2), 5.39 (d, 1H, CH2—N, J = 15.4), 6.26 (s, 1H, –C=CH–), 6.28 (br d, 1H, H3, furyl, J = 3.3), 6.30 (dd, 1H, H4, furyl, J = 1.7, J = 3.3), 6.35 (br d, 1H, H3, furyl, J = 3.3), 6.42 (dd, 1H, H4, furyl, J = 1.7, J = 3.3), 6.51 (d, 1H, H8, J = 7.7), 6.78 (t, 1H, H6, J = 7.7), 7.23 (dt, 1H, H7, J = 1.1, J = 7.7), 7.34 (br d, 1H, H5, furyl, J = 1.7), 7.42 (br d, 1H, H5, furyl, J = 1.7), 7.92 (dd, 1H, H5, J = 1.1, J = 7.7). 13C NMR (CDCl3, 150.9 MHz, 301 K): δ = 13.4 (CH3), 39.7 (CH2—N), 75.8 (C2), 109.0, 110.5, 111.0, 111.5, 113.6, 114.4, 117.9, 118.6, 128.7, 133.4, 133.8, 142.3, 142.4, 145.7, 150.5, 151.8 (CAr, –C=CH–), 162.9 (NCO). MS (EI, 70 eV): m/z = 334 [M]+ (16), 227 (24), 224 (10), 81 (100), 77 (14), 53 (22).
5. Refinement
Crystal data, data collection and structure . X-ray diffraction studies were carried out on the `Belok' beamline of the National Research Center `Kurchatov Institute' (Moscow, Russian Federation) using a Rayonix SX165 CCD detector. A total of 360 images for each compound was collected using an oscillation range of 1.0° (φ scan mode, two different crystal orientations) and corrected for absorption using the SCALA program (Evans, 2006
). The data were indexed, integrated and scaled using the utility iMosflm in the CCP4 programme suite (Battye et al., 2011
).
|
The hydrogen atoms of the amino groups were localized in difference-Fourier maps and refined isotropically with fixed displacement parameters [Uiso(H) = 1.2Ueq(N)]. The other hydrogen atoms were placed in calculated positions with C—H = 0.95–1.00 Å and refined in the riding model with fixed isotropic displacement parameters [Uiso(H) = 1.5Ueq(C-methyl) or 1.2Ueq(C) for all others].
A relatively large number of reflections (a few dozen) were omitted for the following reasons: (1) In order to achieve better I/σ statistics for high-angle reflections, we selected a longer exposure time, which resulted in some intensity overloads in the low-angle part of the area. These corrupted intensities were excluded from final steps of the (2) In the current setup of the instrument, the low-temperature device eclipses a small region of the detector near its high-angle limit. This resulted in zero intensity for some reflections. (3) The quality of the single crystals chosen for the diffraction experiments was far from perfect. Some systematic intensity deviations can be due to extinction and defects present in the crystals.
Supporting information
https://doi.org/10.1107/S2056989018009982/yk2115sup1.cif
contains datablocks global, I, II, III. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989018009982/yk2115Isup2.hkl
Structure factors: contains datablock II. DOI: https://doi.org/10.1107/S2056989018009982/yk2115IIsup3.hkl
Structure factors: contains datablock III. DOI: https://doi.org/10.1107/S2056989018009982/yk2115IIIsup4.hkl
For all structures, data collection: Marccd (Doyle, 2011); cell
iMosflm (Battye et al., 2011); data reduction: iMosflm (Battye et al., 2011); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).C22H20N2O2 | F(000) = 728 |
Mr = 344.40 | Dx = 1.218 Mg m−3 |
Monoclinic, P21/n | Synchrotron radiation, λ = 0.96990 Å |
a = 7.9416 (16) Å | Cell parameters from 500 reflections |
b = 19.202 (4) Å | θ = 3.5–35.0° |
c = 12.497 (3) Å | µ = 0.16 mm−1 |
β = 99.663 (3)° | T = 100 K |
V = 1878.7 (7) Å3 | Needle, colourless |
Z = 4 | 0.25 × 0.08 × 0.03 mm |
Rayonix SX165 CCD diffractometer | 2264 reflections with I > 2σ(I) |
/f scan | Rint = 0.080 |
Absorption correction: multi-scan (SCALA; Evans, 2006) | θmax = 38.4°, θmin = 3.7° |
Tmin = 0.950, Tmax = 0.990 | h = −8→9 |
20568 measured reflections | k = −24→24 |
3781 independent reflections | l = −15→15 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.097 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.218 | w = 1/[σ2(Fo2)] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max < 0.001 |
3781 reflections | Δρmax = 0.37 e Å−3 |
240 parameters | Δρmin = −0.31 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: difference Fourier map | Extinction coefficient: 0.085 (8) |
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 | ||
O1 | 0.28682 (18) | 0.44379 (6) | 0.47756 (11) | 0.0354 (5) | |
O2 | 0.2968 (2) | 0.25305 (7) | 0.07159 (12) | 0.0523 (5) | |
N1 | 0.6282 (3) | 0.24206 (7) | 0.35460 (14) | 0.0350 (5) | |
H1 | 0.701 (3) | 0.2458 (8) | 0.4204 (18) | 0.042* | |
C2 | 0.4453 (3) | 0.24277 (9) | 0.35967 (16) | 0.0346 (6) | |
H2 | 0.4234 | 0.2060 | 0.4124 | 0.042* | |
N3 | 0.3532 (2) | 0.22258 (8) | 0.25120 (12) | 0.0351 (5) | |
C4 | 0.3922 (3) | 0.25582 (9) | 0.16113 (18) | 0.0378 (6) | |
C4A | 0.5591 (3) | 0.29244 (9) | 0.17600 (15) | 0.0347 (6) | |
C5 | 0.6075 (3) | 0.33384 (9) | 0.09282 (15) | 0.0428 (7) | |
H5 | 0.5278 | 0.3418 | 0.0283 | 0.051* | |
C6 | 0.7685 (3) | 0.36302 (10) | 0.10347 (17) | 0.0440 (7) | |
H6 | 0.7987 | 0.3912 | 0.0472 | 0.053* | |
C7 | 0.8863 (3) | 0.35072 (9) | 0.19744 (18) | 0.0437 (6) | |
H7 | 0.9980 | 0.3698 | 0.2039 | 0.052* | |
C8 | 0.8432 (3) | 0.31105 (9) | 0.28204 (17) | 0.0398 (6) | |
H8 | 0.9249 | 0.3032 | 0.3457 | 0.048* | |
C8A | 0.6779 (3) | 0.28254 (9) | 0.27292 (15) | 0.0348 (6) | |
C9 | 0.3811 (3) | 0.31155 (9) | 0.39732 (15) | 0.0353 (6) | |
H9 | 0.3892 | 0.3518 | 0.3543 | 0.042* | |
C10 | 0.3141 (3) | 0.31829 (10) | 0.48751 (16) | 0.0355 (6) | |
H10 | 0.3002 | 0.2769 | 0.5267 | 0.043* | |
C11 | 0.2603 (3) | 0.38264 (9) | 0.53159 (16) | 0.0352 (6) | |
C12 | 0.1939 (3) | 0.39832 (9) | 0.62208 (16) | 0.0415 (6) | |
H12 | 0.1636 | 0.3661 | 0.6733 | 0.050* | |
C13 | 0.1783 (3) | 0.47279 (10) | 0.62563 (16) | 0.0417 (6) | |
H13 | 0.1359 | 0.4991 | 0.6798 | 0.050* | |
C14 | 0.2355 (3) | 0.49853 (9) | 0.53705 (17) | 0.0355 (6) | |
C15 | 0.2558 (3) | 0.56945 (8) | 0.49272 (18) | 0.0433 (6) | |
H15A | 0.3767 | 0.5780 | 0.4903 | 0.065* | |
H15B | 0.2143 | 0.6042 | 0.5395 | 0.065* | |
H15C | 0.1897 | 0.5728 | 0.4193 | 0.065* | |
C16 | 0.1931 (3) | 0.18476 (10) | 0.24752 (16) | 0.0416 (6) | |
H16A | 0.1365 | 0.1808 | 0.1709 | 0.050* | |
H16B | 0.1170 | 0.2122 | 0.2866 | 0.050* | |
C17 | 0.2130 (3) | 0.11236 (10) | 0.29657 (16) | 0.0377 (6) | |
C18 | 0.0692 (3) | 0.07756 (11) | 0.31936 (18) | 0.0490 (7) | |
H18 | −0.0384 | 0.1003 | 0.3063 | 0.059* | |
C19 | 0.0799 (4) | 0.00989 (12) | 0.3611 (2) | 0.0599 (8) | |
H19 | −0.0201 | −0.0134 | 0.3744 | 0.072* | |
C20 | 0.2384 (4) | −0.02327 (12) | 0.38311 (18) | 0.0601 (8) | |
H20 | 0.2472 | −0.0691 | 0.4121 | 0.072* | |
C21 | 0.3821 (4) | 0.01103 (10) | 0.36237 (16) | 0.0485 (7) | |
H21 | 0.4904 | −0.0112 | 0.3779 | 0.058* | |
C22 | 0.3698 (3) | 0.07805 (10) | 0.31880 (16) | 0.0410 (7) | |
H22 | 0.4697 | 0.1007 | 0.3040 | 0.049* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0423 (11) | 0.0291 (8) | 0.0371 (9) | −0.0006 (6) | 0.0135 (7) | −0.0021 (5) |
O2 | 0.0677 (14) | 0.0512 (10) | 0.0321 (10) | −0.0035 (8) | −0.0082 (9) | 0.0004 (6) |
N1 | 0.0476 (15) | 0.0303 (10) | 0.0265 (10) | 0.0035 (8) | 0.0042 (9) | 0.0001 (7) |
C2 | 0.0437 (17) | 0.0324 (11) | 0.0278 (12) | 0.0006 (9) | 0.0066 (11) | −0.0010 (8) |
N3 | 0.0454 (14) | 0.0274 (9) | 0.0314 (10) | −0.0021 (8) | 0.0028 (9) | −0.0021 (7) |
C4 | 0.0564 (19) | 0.0256 (10) | 0.0298 (13) | 0.0040 (10) | 0.0024 (12) | −0.0020 (9) |
C4A | 0.0507 (17) | 0.0254 (10) | 0.0286 (12) | 0.0041 (10) | 0.0088 (11) | −0.0025 (8) |
C5 | 0.069 (2) | 0.0277 (11) | 0.0327 (13) | 0.0061 (12) | 0.0115 (12) | −0.0006 (8) |
C6 | 0.069 (2) | 0.0262 (11) | 0.0415 (14) | −0.0023 (12) | 0.0215 (13) | 0.0001 (9) |
C7 | 0.0540 (18) | 0.0276 (11) | 0.0528 (15) | −0.0001 (10) | 0.0192 (14) | −0.0041 (10) |
C8 | 0.0499 (18) | 0.0288 (11) | 0.0418 (13) | 0.0049 (10) | 0.0110 (12) | −0.0034 (9) |
C8A | 0.0512 (17) | 0.0240 (10) | 0.0302 (12) | 0.0036 (10) | 0.0095 (11) | −0.0020 (8) |
C9 | 0.0477 (16) | 0.0259 (10) | 0.0324 (12) | −0.0009 (9) | 0.0069 (11) | −0.0011 (8) |
C10 | 0.0397 (16) | 0.0287 (11) | 0.0382 (12) | −0.0031 (9) | 0.0076 (11) | −0.0008 (8) |
C11 | 0.0428 (16) | 0.0291 (11) | 0.0357 (12) | −0.0006 (10) | 0.0125 (11) | 0.0002 (8) |
C12 | 0.0507 (17) | 0.0327 (11) | 0.0438 (14) | 0.0032 (10) | 0.0158 (12) | 0.0045 (9) |
C13 | 0.0508 (17) | 0.0380 (12) | 0.0396 (13) | 0.0078 (11) | 0.0168 (12) | −0.0041 (9) |
C14 | 0.0389 (15) | 0.0289 (11) | 0.0382 (12) | 0.0021 (9) | 0.0048 (11) | −0.0066 (9) |
C15 | 0.0516 (18) | 0.0313 (12) | 0.0471 (14) | 0.0006 (10) | 0.0084 (12) | −0.0017 (9) |
C16 | 0.0421 (17) | 0.0343 (12) | 0.0463 (14) | 0.0005 (11) | 0.0016 (11) | −0.0091 (9) |
C17 | 0.0490 (17) | 0.0306 (11) | 0.0336 (12) | −0.0009 (11) | 0.0070 (11) | −0.0057 (9) |
C18 | 0.0476 (18) | 0.0475 (14) | 0.0512 (15) | −0.0068 (12) | 0.0063 (12) | −0.0027 (11) |
C19 | 0.063 (2) | 0.0498 (15) | 0.0672 (18) | −0.0180 (14) | 0.0125 (15) | 0.0054 (11) |
C20 | 0.088 (2) | 0.0374 (13) | 0.0567 (16) | −0.0095 (15) | 0.0158 (15) | 0.0045 (11) |
C21 | 0.071 (2) | 0.0307 (12) | 0.0466 (14) | 0.0065 (12) | 0.0193 (13) | 0.0005 (10) |
C22 | 0.0602 (19) | 0.0296 (11) | 0.0371 (13) | 0.0012 (11) | 0.0192 (12) | −0.0031 (9) |
O1—C14 | 1.388 (2) | C10—H10 | 0.9500 |
O1—C11 | 1.388 (2) | C11—C12 | 1.359 (3) |
O2—C4 | 1.243 (2) | C12—C13 | 1.437 (3) |
N1—C8A | 1.392 (2) | C12—H12 | 0.9500 |
N1—C2 | 1.465 (3) | C13—C14 | 1.358 (3) |
N1—H1 | 0.92 (2) | C13—H13 | 0.9500 |
C2—N3 | 1.480 (3) | C14—C15 | 1.489 (2) |
C2—C9 | 1.518 (2) | C15—H15A | 0.9800 |
C2—H2 | 1.0000 | C15—H15B | 0.9800 |
N3—C4 | 1.374 (2) | C15—H15C | 0.9800 |
N3—C16 | 1.459 (3) | C16—C17 | 1.517 (3) |
C4—C4A | 1.485 (3) | C16—H16A | 0.9900 |
C4A—C5 | 1.412 (2) | C16—H16B | 0.9900 |
C4A—C8A | 1.417 (3) | C17—C18 | 1.393 (3) |
C5—C6 | 1.382 (3) | C17—C22 | 1.394 (3) |
C5—H5 | 0.9500 | C18—C19 | 1.397 (3) |
C6—C7 | 1.393 (3) | C18—H18 | 0.9500 |
C6—H6 | 0.9500 | C19—C20 | 1.396 (4) |
C7—C8 | 1.392 (3) | C19—H19 | 0.9500 |
C7—H7 | 0.9500 | C20—C21 | 1.380 (3) |
C8—C8A | 1.410 (3) | C20—H20 | 0.9500 |
C8—H8 | 0.9500 | C21—C22 | 1.394 (2) |
C9—C10 | 1.331 (2) | C21—H21 | 0.9500 |
C9—H9 | 0.9500 | C22—H22 | 0.9500 |
C10—C11 | 1.446 (2) | ||
C14—O1—C11 | 107.34 (15) | C12—C11—C10 | 133.37 (18) |
C8A—N1—C2 | 115.58 (17) | O1—C11—C10 | 117.32 (17) |
C8A—N1—H1 | 113.4 (12) | C11—C12—C13 | 107.09 (16) |
C2—N1—H1 | 116.0 (13) | C11—C12—H12 | 126.5 |
N1—C2—N3 | 107.40 (15) | C13—C12—H12 | 126.5 |
N1—C2—C9 | 114.10 (15) | C14—C13—C12 | 107.13 (15) |
N3—C2—C9 | 111.83 (16) | C14—C13—H13 | 126.4 |
N1—C2—H2 | 107.8 | C12—C13—H13 | 126.4 |
N3—C2—H2 | 107.8 | C13—C14—O1 | 109.23 (15) |
C9—C2—H2 | 107.8 | C13—C14—C15 | 135.07 (18) |
C4—N3—C16 | 121.37 (18) | O1—C14—C15 | 115.69 (17) |
C4—N3—C2 | 118.97 (17) | C14—C15—H15A | 109.5 |
C16—N3—C2 | 116.97 (15) | C14—C15—H15B | 109.5 |
O2—C4—N3 | 122.1 (2) | H15A—C15—H15B | 109.5 |
O2—C4—C4A | 121.97 (19) | C14—C15—H15C | 109.5 |
N3—C4—C4A | 115.89 (19) | H15A—C15—H15C | 109.5 |
C5—C4A—C8A | 118.7 (2) | H15B—C15—H15C | 109.5 |
C5—C4A—C4 | 121.5 (2) | N3—C16—C17 | 114.34 (19) |
C8A—C4A—C4 | 119.71 (18) | N3—C16—H16A | 108.7 |
C6—C5—C4A | 121.3 (2) | C17—C16—H16A | 108.7 |
C6—C5—H5 | 119.4 | N3—C16—H16B | 108.7 |
C4A—C5—H5 | 119.4 | C17—C16—H16B | 108.7 |
C5—C6—C7 | 119.46 (18) | H16A—C16—H16B | 107.6 |
C5—C6—H6 | 120.3 | C18—C17—C22 | 117.9 (2) |
C7—C6—H6 | 120.3 | C18—C17—C16 | 119.2 (2) |
C8—C7—C6 | 121.1 (2) | C22—C17—C16 | 122.9 (2) |
C8—C7—H7 | 119.4 | C17—C18—C19 | 121.5 (2) |
C6—C7—H7 | 119.4 | C17—C18—H18 | 119.3 |
C7—C8—C8A | 119.7 (2) | C19—C18—H18 | 119.3 |
C7—C8—H8 | 120.1 | C20—C19—C18 | 119.6 (2) |
C8A—C8—H8 | 120.1 | C20—C19—H19 | 120.2 |
N1—C8A—C8 | 122.2 (2) | C18—C19—H19 | 120.2 |
N1—C8A—C4A | 118.1 (2) | C21—C20—C19 | 119.5 (2) |
C8—C8A—C4A | 119.62 (18) | C21—C20—H20 | 120.3 |
C10—C9—C2 | 123.34 (17) | C19—C20—H20 | 120.3 |
C10—C9—H9 | 118.3 | C20—C21—C22 | 120.5 (2) |
C2—C9—H9 | 118.3 | C20—C21—H21 | 119.7 |
C9—C10—C11 | 126.24 (18) | C22—C21—H21 | 119.7 |
C9—C10—H10 | 116.9 | C21—C22—C17 | 121.1 (2) |
C11—C10—H10 | 116.9 | C21—C22—H22 | 119.5 |
C12—C11—O1 | 109.20 (16) | C17—C22—H22 | 119.5 |
C8A—N1—C2—N3 | 54.70 (19) | N1—C2—C9—C10 | −117.6 (2) |
C8A—N1—C2—C9 | −69.8 (2) | N3—C2—C9—C10 | 120.2 (2) |
N1—C2—N3—C4 | −49.9 (2) | C2—C9—C10—C11 | 175.94 (19) |
C9—C2—N3—C4 | 76.0 (2) | C14—O1—C11—C12 | 0.2 (2) |
N1—C2—N3—C16 | 148.38 (16) | C14—O1—C11—C10 | −176.56 (17) |
C9—C2—N3—C16 | −85.71 (19) | C9—C10—C11—C12 | −178.5 (2) |
C16—N3—C4—O2 | −2.9 (3) | C9—C10—C11—O1 | −2.7 (3) |
C2—N3—C4—O2 | −163.75 (17) | O1—C11—C12—C13 | −0.2 (2) |
C16—N3—C4—C4A | 179.93 (16) | C10—C11—C12—C13 | 175.8 (2) |
C2—N3—C4—C4A | 19.1 (2) | C11—C12—C13—C14 | 0.1 (2) |
O2—C4—C4A—C5 | 8.7 (3) | C12—C13—C14—O1 | 0.0 (2) |
N3—C4—C4A—C5 | −174.14 (15) | C12—C13—C14—C15 | −179.3 (3) |
O2—C4—C4A—C8A | −167.33 (16) | C11—O1—C14—C13 | −0.1 (2) |
N3—C4—C4A—C8A | 9.8 (3) | C11—O1—C14—C15 | 179.34 (18) |
C8A—C4A—C5—C6 | 1.6 (3) | C4—N3—C16—C17 | 131.92 (18) |
C4—C4A—C5—C6 | −174.45 (18) | C2—N3—C16—C17 | −66.9 (2) |
C4A—C5—C6—C7 | 0.8 (3) | N3—C16—C17—C18 | 165.99 (17) |
C5—C6—C7—C8 | −1.7 (3) | N3—C16—C17—C22 | −15.0 (3) |
C6—C7—C8—C8A | 0.1 (3) | C22—C17—C18—C19 | −1.3 (3) |
C2—N1—C8A—C8 | 152.99 (17) | C16—C17—C18—C19 | 177.8 (2) |
C2—N1—C8A—C4A | −29.7 (2) | C17—C18—C19—C20 | 1.6 (3) |
C7—C8—C8A—N1 | 179.53 (15) | C18—C19—C20—C21 | −0.6 (4) |
C7—C8—C8A—C4A | 2.3 (3) | C19—C20—C21—C22 | −0.6 (3) |
C5—C4A—C8A—N1 | 179.53 (15) | C20—C21—C22—C17 | 0.9 (3) |
C4—C4A—C8A—N1 | −4.3 (3) | C18—C17—C22—C21 | 0.1 (3) |
C5—C4A—C8A—C8 | −3.1 (3) | C16—C17—C22—C21 | −178.98 (17) |
C4—C4A—C8A—C8 | 172.99 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2i | 0.92 (2) | 1.92 (2) | 2.817 (2) | 164.4 (19) |
Symmetry code: (i) x+1/2, −y+1/2, z+1/2. |
C22H20N2O2 | Dx = 1.286 Mg m−3 |
Mr = 344.40 | Synchrotron radiation, λ = 0.96990 Å |
Orthorhombic, Pbca | Cell parameters from 500 reflections |
a = 13.921 (3) Å | θ = 3.2–32.0° |
b = 11.296 (2) Å | µ = 0.17 mm−1 |
c = 22.623 (5) Å | T = 100 K |
V = 3557.5 (13) Å3 | Plate, colourless |
Z = 8 | 0.20 × 0.15 × 0.01 mm |
F(000) = 1456 |
Rayonix SX165 CCD diffractometer | 2411 reflections with I > 2σ(I) |
/f scan | Rint = 0.070 |
Absorption correction: multi-scan (SCALA; Evans, 2006) | θmax = 38.4°, θmin = 3.2° |
Tmin = 0.960, Tmax = 0.990 | h = −17→17 |
18942 measured reflections | k = −14→14 |
3764 independent reflections | l = −28→28 |
Refinement on F2 | Secondary atom site location: difmap2 |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.074 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.190 | w = 1/[σ2(Fo2) + 2P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
3764 reflections | Δρmax = 0.30 e Å−3 |
240 parameters | Δρmin = −0.28 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: difference Fourier map | Extinction coefficient: 0.0102 (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 | ||
O1 | 0.54343 (13) | 0.33368 (16) | 0.38217 (8) | 0.0430 (5) | |
O2 | 0.13105 (12) | 0.75727 (16) | 0.49206 (8) | 0.0405 (5) | |
N1 | 0.42208 (15) | 0.77868 (19) | 0.48819 (9) | 0.0339 (5) | |
H1 | 0.486 (2) | 0.772 (2) | 0.4927 (11) | 0.041* | |
C2 | 0.37955 (17) | 0.6658 (2) | 0.47071 (11) | 0.0328 (6) | |
H2 | 0.3889 | 0.6072 | 0.5033 | 0.039* | |
N3 | 0.27451 (14) | 0.68234 (18) | 0.46041 (9) | 0.0326 (5) | |
C4 | 0.21959 (18) | 0.7574 (2) | 0.49452 (11) | 0.0329 (6) | |
C4A | 0.27357 (17) | 0.8430 (2) | 0.53208 (11) | 0.0329 (6) | |
C5 | 0.22296 (18) | 0.9208 (2) | 0.56907 (11) | 0.0364 (6) | |
H5 | 0.1552 | 0.9134 | 0.5727 | 0.044* | |
C6 | 0.27111 (19) | 1.0090 (2) | 0.60050 (11) | 0.0395 (7) | |
H6 | 0.2366 | 1.0619 | 0.6252 | 0.047* | |
C7 | 0.3704 (2) | 1.0183 (2) | 0.59511 (11) | 0.0392 (6) | |
H7 | 0.4035 | 1.0785 | 0.6162 | 0.047* | |
C8 | 0.42221 (18) | 0.9407 (2) | 0.55936 (11) | 0.0365 (6) | |
H8 | 0.4901 | 0.9476 | 0.5566 | 0.044* | |
C8A | 0.37381 (17) | 0.8521 (2) | 0.52727 (10) | 0.0317 (6) | |
C9 | 0.43039 (16) | 0.6209 (2) | 0.41535 (11) | 0.0319 (6) | |
C10 | 0.46061 (16) | 0.5072 (2) | 0.41468 (11) | 0.0334 (6) | |
H10 | 0.4491 | 0.4625 | 0.4495 | 0.040* | |
C11 | 0.50873 (17) | 0.4455 (2) | 0.36658 (11) | 0.0354 (6) | |
C12 | 0.52915 (19) | 0.4665 (2) | 0.30866 (12) | 0.0421 (7) | |
H12 | 0.5136 | 0.5356 | 0.2867 | 0.051* | |
C13 | 0.5792 (2) | 0.3627 (3) | 0.28702 (12) | 0.0441 (7) | |
H13 | 0.6028 | 0.3503 | 0.2481 | 0.053* | |
C14 | 0.5856 (2) | 0.2871 (3) | 0.33296 (13) | 0.0461 (7) | |
H14 | 0.6156 | 0.2116 | 0.3313 | 0.055* | |
C15 | 0.4437 (2) | 0.7071 (2) | 0.36493 (11) | 0.0405 (7) | |
H15A | 0.5122 | 0.7138 | 0.3555 | 0.061* | |
H15B | 0.4188 | 0.7849 | 0.3765 | 0.061* | |
H15C | 0.4087 | 0.6786 | 0.3301 | 0.061* | |
C16 | 0.22429 (17) | 0.5853 (2) | 0.42882 (11) | 0.0356 (6) | |
H16A | 0.1591 | 0.5760 | 0.4456 | 0.043* | |
H16B | 0.2595 | 0.5104 | 0.4354 | 0.043* | |
C17 | 0.21601 (17) | 0.6074 (2) | 0.36272 (11) | 0.0337 (6) | |
C18 | 0.16896 (19) | 0.7080 (2) | 0.34142 (12) | 0.0387 (6) | |
H18 | 0.1399 | 0.7615 | 0.3684 | 0.046* | |
C19 | 0.1643 (2) | 0.7306 (2) | 0.28113 (12) | 0.0406 (7) | |
H19 | 0.1317 | 0.7992 | 0.2673 | 0.049* | |
C20 | 0.2067 (2) | 0.6539 (3) | 0.24086 (12) | 0.0428 (7) | |
H20 | 0.2048 | 0.6708 | 0.1997 | 0.051* | |
C21 | 0.2521 (2) | 0.5522 (3) | 0.26139 (13) | 0.0461 (7) | |
H21 | 0.2803 | 0.4983 | 0.2343 | 0.055* | |
C22 | 0.25596 (19) | 0.5296 (2) | 0.32196 (12) | 0.0421 (7) | |
H22 | 0.2865 | 0.4596 | 0.3356 | 0.051* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0384 (11) | 0.0384 (11) | 0.0522 (12) | 0.0046 (8) | 0.0039 (9) | −0.0038 (9) |
O2 | 0.0210 (9) | 0.0485 (11) | 0.0520 (12) | 0.0021 (8) | 0.0008 (8) | 0.0008 (9) |
N1 | 0.0192 (10) | 0.0379 (13) | 0.0445 (13) | 0.0006 (9) | 0.0006 (9) | −0.0058 (10) |
C2 | 0.0225 (12) | 0.0362 (14) | 0.0397 (14) | −0.0014 (10) | −0.0003 (10) | 0.0011 (11) |
N3 | 0.0210 (10) | 0.0353 (12) | 0.0415 (12) | −0.0007 (8) | 0.0012 (9) | −0.0012 (10) |
C4 | 0.0243 (12) | 0.0374 (14) | 0.0370 (14) | 0.0021 (10) | 0.0016 (10) | 0.0050 (11) |
C4A | 0.0250 (13) | 0.0368 (14) | 0.0369 (14) | 0.0040 (10) | 0.0014 (10) | 0.0034 (11) |
C5 | 0.0284 (13) | 0.0405 (15) | 0.0404 (14) | 0.0057 (11) | 0.0025 (11) | 0.0034 (12) |
C6 | 0.0384 (15) | 0.0401 (15) | 0.0400 (15) | 0.0085 (12) | 0.0013 (12) | 0.0007 (12) |
C7 | 0.0397 (15) | 0.0359 (14) | 0.0421 (15) | 0.0002 (11) | −0.0026 (12) | −0.0011 (12) |
C8 | 0.0274 (12) | 0.0369 (14) | 0.0452 (15) | −0.0001 (11) | −0.0006 (11) | −0.0018 (12) |
C8A | 0.0277 (13) | 0.0332 (13) | 0.0341 (14) | 0.0024 (10) | 0.0013 (10) | 0.0025 (11) |
C9 | 0.0217 (11) | 0.0358 (14) | 0.0383 (14) | −0.0013 (10) | 0.0011 (10) | 0.0000 (11) |
C10 | 0.0222 (11) | 0.0396 (15) | 0.0383 (14) | −0.0004 (10) | 0.0004 (10) | −0.0024 (12) |
C11 | 0.0252 (12) | 0.0343 (14) | 0.0466 (15) | 0.0003 (10) | −0.0023 (11) | −0.0021 (12) |
C12 | 0.0397 (15) | 0.0427 (16) | 0.0439 (16) | −0.0075 (12) | −0.0004 (13) | −0.0037 (13) |
C13 | 0.0394 (16) | 0.0513 (18) | 0.0415 (16) | −0.0040 (13) | 0.0065 (12) | −0.0111 (14) |
C14 | 0.0383 (15) | 0.0447 (17) | 0.0554 (18) | 0.0001 (13) | 0.0061 (13) | −0.0124 (15) |
C15 | 0.0373 (15) | 0.0397 (16) | 0.0446 (16) | −0.0034 (12) | 0.0027 (12) | −0.0015 (12) |
C16 | 0.0233 (12) | 0.0335 (14) | 0.0500 (16) | −0.0038 (10) | −0.0020 (11) | −0.0011 (12) |
C17 | 0.0217 (11) | 0.0326 (13) | 0.0467 (15) | −0.0025 (10) | −0.0028 (10) | −0.0032 (12) |
C18 | 0.0339 (14) | 0.0350 (14) | 0.0471 (16) | 0.0030 (11) | 0.0001 (12) | −0.0014 (12) |
C19 | 0.0380 (15) | 0.0338 (14) | 0.0499 (17) | 0.0027 (11) | −0.0050 (13) | −0.0001 (12) |
C20 | 0.0343 (15) | 0.0474 (17) | 0.0467 (16) | −0.0043 (12) | −0.0052 (12) | −0.0032 (13) |
C21 | 0.0382 (16) | 0.0508 (17) | 0.0493 (18) | 0.0058 (13) | −0.0048 (13) | −0.0154 (14) |
C22 | 0.0365 (14) | 0.0375 (15) | 0.0524 (18) | 0.0043 (12) | −0.0118 (12) | −0.0084 (13) |
O1—C14 | 1.364 (3) | C10—H10 | 0.9500 |
O1—C11 | 1.398 (3) | C11—C12 | 1.362 (4) |
O2—C4 | 1.234 (3) | C12—C13 | 1.449 (4) |
N1—C8A | 1.386 (3) | C12—H12 | 0.9500 |
N1—C2 | 1.460 (3) | C13—C14 | 1.348 (4) |
N1—H1 | 0.90 (3) | C13—H13 | 0.9500 |
C2—N3 | 1.493 (3) | C14—H14 | 0.9500 |
C2—C9 | 1.525 (3) | C15—H15A | 0.9800 |
C2—H2 | 1.0000 | C15—H15B | 0.9800 |
N3—C4 | 1.378 (3) | C15—H15C | 0.9800 |
N3—C16 | 1.483 (3) | C16—C17 | 1.520 (4) |
C4—C4A | 1.490 (4) | C16—H16A | 0.9900 |
C4A—C8A | 1.403 (3) | C16—H16B | 0.9900 |
C4A—C5 | 1.404 (3) | C17—C22 | 1.390 (4) |
C5—C6 | 1.395 (4) | C17—C18 | 1.398 (4) |
C5—H5 | 0.9500 | C18—C19 | 1.389 (4) |
C6—C7 | 1.392 (4) | C18—H18 | 0.9500 |
C6—H6 | 0.9500 | C19—C20 | 1.389 (4) |
C7—C8 | 1.393 (4) | C19—H19 | 0.9500 |
C7—H7 | 0.9500 | C20—C21 | 1.391 (4) |
C8—C8A | 1.408 (3) | C20—H20 | 0.9500 |
C8—H8 | 0.9500 | C21—C22 | 1.395 (4) |
C9—C10 | 1.351 (3) | C21—H21 | 0.9500 |
C9—C15 | 1.511 (4) | C22—H22 | 0.9500 |
C10—C11 | 1.455 (3) | ||
C14—O1—C11 | 107.0 (2) | C12—C11—C10 | 137.1 (2) |
C8A—N1—C2 | 119.9 (2) | O1—C11—C10 | 113.8 (2) |
C8A—N1—H1 | 117.1 (16) | C11—C12—C13 | 106.5 (2) |
C2—N1—H1 | 111.2 (17) | C11—C12—H12 | 126.7 |
N1—C2—N3 | 109.3 (2) | C13—C12—H12 | 126.7 |
N1—C2—C9 | 108.9 (2) | C14—C13—C12 | 106.5 (2) |
N3—C2—C9 | 111.59 (19) | C14—C13—H13 | 126.7 |
N1—C2—H2 | 109.0 | C12—C13—H13 | 126.7 |
N3—C2—H2 | 109.0 | C13—C14—O1 | 110.9 (3) |
C9—C2—H2 | 109.0 | C13—C14—H14 | 124.6 |
C4—N3—C16 | 117.6 (2) | O1—C14—H14 | 124.6 |
C4—N3—C2 | 122.2 (2) | C9—C15—H15A | 109.5 |
C16—N3—C2 | 116.39 (19) | C9—C15—H15B | 109.5 |
O2—C4—N3 | 121.9 (2) | H15A—C15—H15B | 109.5 |
O2—C4—C4A | 122.0 (2) | C9—C15—H15C | 109.5 |
N3—C4—C4A | 116.0 (2) | H15A—C15—H15C | 109.5 |
C8A—C4A—C5 | 119.9 (2) | H15B—C15—H15C | 109.5 |
C8A—C4A—C4 | 120.3 (2) | N3—C16—C17 | 112.9 (2) |
C5—C4A—C4 | 119.5 (2) | N3—C16—H16A | 109.0 |
C6—C5—C4A | 120.7 (2) | C17—C16—H16A | 109.0 |
C6—C5—H5 | 119.7 | N3—C16—H16B | 109.0 |
C4A—C5—H5 | 119.7 | C17—C16—H16B | 109.0 |
C7—C6—C5 | 119.1 (2) | H16A—C16—H16B | 107.8 |
C7—C6—H6 | 120.4 | C22—C17—C18 | 118.2 (2) |
C5—C6—H6 | 120.4 | C22—C17—C16 | 121.2 (2) |
C6—C7—C8 | 121.2 (2) | C18—C17—C16 | 120.5 (2) |
C6—C7—H7 | 119.4 | C19—C18—C17 | 120.6 (2) |
C8—C7—H7 | 119.4 | C19—C18—H18 | 119.7 |
C7—C8—C8A | 119.9 (2) | C17—C18—H18 | 119.7 |
C7—C8—H8 | 120.1 | C18—C19—C20 | 120.6 (3) |
C8A—C8—H8 | 120.1 | C18—C19—H19 | 119.7 |
N1—C8A—C4A | 119.2 (2) | C20—C19—H19 | 119.7 |
N1—C8A—C8 | 121.5 (2) | C19—C20—C21 | 119.3 (3) |
C4A—C8A—C8 | 119.2 (2) | C19—C20—H20 | 120.4 |
C10—C9—C15 | 124.5 (2) | C21—C20—H20 | 120.4 |
C10—C9—C2 | 118.0 (2) | C20—C21—C22 | 119.8 (3) |
C15—C9—C2 | 117.5 (2) | C20—C21—H21 | 120.1 |
C9—C10—C11 | 127.3 (2) | C22—C21—H21 | 120.1 |
C9—C10—H10 | 116.3 | C17—C22—C21 | 121.4 (3) |
C11—C10—H10 | 116.3 | C17—C22—H22 | 119.3 |
C12—C11—O1 | 109.1 (2) | C21—C22—H22 | 119.3 |
C8A—N1—C2—N3 | 41.3 (3) | N1—C2—C9—C10 | 131.6 (2) |
C8A—N1—C2—C9 | 163.4 (2) | N3—C2—C9—C10 | −107.7 (2) |
N1—C2—N3—C4 | −36.7 (3) | N1—C2—C9—C15 | −48.3 (3) |
C9—C2—N3—C4 | −157.3 (2) | N3—C2—C9—C15 | 72.5 (3) |
N1—C2—N3—C16 | 165.83 (19) | C15—C9—C10—C11 | −1.3 (4) |
C9—C2—N3—C16 | 45.3 (3) | C2—C9—C10—C11 | 178.8 (2) |
C16—N3—C4—O2 | −11.4 (3) | C14—O1—C11—C12 | 0.3 (3) |
C2—N3—C4—O2 | −168.5 (2) | C14—O1—C11—C10 | 179.6 (2) |
C16—N3—C4—C4A | 171.8 (2) | C9—C10—C11—C12 | −9.7 (5) |
C2—N3—C4—C4A | 14.6 (3) | C9—C10—C11—O1 | 171.3 (2) |
O2—C4—C4A—C8A | −170.6 (2) | O1—C11—C12—C13 | −0.1 (3) |
N3—C4—C4A—C8A | 6.2 (3) | C10—C11—C12—C13 | −179.2 (3) |
O2—C4—C4A—C5 | 4.5 (4) | C11—C12—C13—C14 | −0.1 (3) |
N3—C4—C4A—C5 | −178.7 (2) | C12—C13—C14—O1 | 0.3 (3) |
C8A—C4A—C5—C6 | 1.1 (4) | C11—O1—C14—C13 | −0.4 (3) |
C4—C4A—C5—C6 | −174.0 (2) | C4—N3—C16—C17 | 106.2 (2) |
C4A—C5—C6—C7 | −0.5 (4) | C2—N3—C16—C17 | −95.3 (2) |
C5—C6—C7—C8 | −0.5 (4) | N3—C16—C17—C22 | 120.2 (3) |
C6—C7—C8—C8A | 0.9 (4) | N3—C16—C17—C18 | −58.8 (3) |
C2—N1—C8A—C4A | −24.3 (3) | C22—C17—C18—C19 | −1.4 (4) |
C2—N1—C8A—C8 | 159.8 (2) | C16—C17—C18—C19 | 177.7 (2) |
C5—C4A—C8A—N1 | −176.6 (2) | C17—C18—C19—C20 | −0.4 (4) |
C4—C4A—C8A—N1 | −1.5 (4) | C18—C19—C20—C21 | 1.6 (4) |
C5—C4A—C8A—C8 | −0.7 (4) | C19—C20—C21—C22 | −1.2 (4) |
C4—C4A—C8A—C8 | 174.4 (2) | C18—C17—C22—C21 | 1.8 (4) |
C7—C8—C8A—N1 | 175.5 (2) | C16—C17—C22—C21 | −177.2 (2) |
C7—C8—C8A—C4A | −0.3 (4) | C20—C21—C22—C17 | −0.6 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2i | 0.90 (3) | 2.07 (3) | 2.971 (3) | 174 (2) |
Symmetry code: (i) x+1/2, −y+3/2, −z+1. |
C20H18N2O3 | Dx = 1.334 Mg m−3 |
Mr = 334.36 | Synchrotron radiation, λ = 0.96990 Å |
Orthorhombic, Pbca | Cell parameters from 600 reflections |
a = 13.928 (3) Å | θ = 3.2–32.0° |
b = 10.684 (2) Å | µ = 0.19 mm−1 |
c = 22.368 (5) Å | T = 100 K |
V = 3328.5 (12) Å3 | Plate, yellow |
Z = 8 | 0.30 × 0.30 × 0.07 mm |
F(000) = 1408 |
Rayonix SX165 CCD diffractometer | 2414 reflections with I > 2σ(I) |
/f scan | Rint = 0.097 |
Absorption correction: multi-scan (SCALA; Evans, 2006) | θmax = 38.4°, θmin = 3.2° |
Tmin = 0.940, Tmax = 0.980 | h = −17→17 |
27461 measured reflections | k = −13→13 |
3460 independent reflections | l = −26→26 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.089 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.224 | w = 1/[σ2(Fo2) + (0.05P)2 + 6P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
3460 reflections | Δρmax = 0.42 e Å−3 |
231 parameters | Δρmin = −0.57 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: difference Fourier map | Extinction coefficient: 0.0078 (7) |
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 | ||
O1 | 0.53713 (18) | 0.6665 (2) | 0.63004 (12) | 0.0493 (7) | |
O2 | 0.1753 (2) | 0.2666 (3) | 0.64505 (16) | 0.0672 (9) | |
O3 | 0.12657 (16) | 0.2418 (3) | 0.49520 (14) | 0.0646 (9) | |
N1 | 0.41678 (19) | 0.2216 (3) | 0.50272 (13) | 0.0392 (7) | |
H1 | 0.483 (3) | 0.224 (3) | 0.5002 (16) | 0.047* | |
C2 | 0.3738 (2) | 0.3381 (3) | 0.52287 (15) | 0.0390 (8) | |
H2 | 0.3852 | 0.4045 | 0.4922 | 0.047* | |
N3 | 0.26847 (17) | 0.3192 (3) | 0.53043 (13) | 0.0432 (8) | |
C4 | 0.2161 (2) | 0.2432 (4) | 0.49362 (18) | 0.0475 (10) | |
C4A | 0.2709 (2) | 0.1577 (3) | 0.45443 (16) | 0.0434 (9) | |
C5 | 0.2225 (3) | 0.0789 (4) | 0.41411 (19) | 0.0551 (11) | |
H5 | 0.1550 | 0.0868 | 0.4093 | 0.066* | |
C6 | 0.2718 (3) | −0.0095 (4) | 0.3815 (2) | 0.0597 (12) | |
H6 | 0.2387 | −0.0630 | 0.3546 | 0.072* | |
C7 | 0.3707 (3) | −0.0196 (4) | 0.38855 (19) | 0.0537 (10) | |
H7 | 0.4049 | −0.0808 | 0.3663 | 0.064* | |
C8 | 0.4203 (3) | 0.0584 (3) | 0.42746 (17) | 0.0461 (9) | |
H8 | 0.4879 | 0.0506 | 0.4314 | 0.055* | |
C8A | 0.3708 (2) | 0.1484 (3) | 0.46093 (15) | 0.0390 (8) | |
C9 | 0.4206 (2) | 0.3773 (3) | 0.58156 (15) | 0.0346 (7) | |
C10 | 0.4528 (2) | 0.4952 (3) | 0.58733 (15) | 0.0357 (7) | |
H10 | 0.4455 | 0.5483 | 0.5536 | 0.043* | |
C11 | 0.4974 (2) | 0.5494 (3) | 0.63964 (15) | 0.0374 (8) | |
C12 | 0.5116 (3) | 0.5158 (3) | 0.69790 (16) | 0.0477 (9) | |
H12 | 0.4917 | 0.4401 | 0.7164 | 0.057* | |
C13 | 0.5625 (3) | 0.6176 (4) | 0.72574 (19) | 0.0569 (11) | |
H13 | 0.5826 | 0.6224 | 0.7663 | 0.068* | |
C14 | 0.5760 (3) | 0.7043 (4) | 0.68329 (19) | 0.0533 (10) | |
H14 | 0.6083 | 0.7816 | 0.6893 | 0.064* | |
C15 | 0.4279 (2) | 0.2790 (3) | 0.62950 (16) | 0.0388 (8) | |
H15A | 0.4948 | 0.2721 | 0.6428 | 0.058* | |
H15B | 0.4065 | 0.1983 | 0.6135 | 0.058* | |
H15C | 0.3873 | 0.3026 | 0.6635 | 0.058* | |
C16 | 0.2168 (2) | 0.4154 (4) | 0.56476 (18) | 0.0523 (10) | |
H16A | 0.1519 | 0.4261 | 0.5476 | 0.063* | |
H16B | 0.2512 | 0.4961 | 0.5607 | 0.063* | |
C17 | 0.2076 (2) | 0.3842 (3) | 0.62962 (17) | 0.0402 (8) | |
C18 | 0.2340 (3) | 0.4544 (3) | 0.67787 (16) | 0.0546 (11) | |
H18 | 0.2623 | 0.5353 | 0.6783 | 0.066* | |
C19 | 0.2087 (4) | 0.3767 (5) | 0.7279 (2) | 0.0819 (17) | |
H19 | 0.2137 | 0.4003 | 0.7687 | 0.098* | |
C20 | 0.1777 (3) | 0.2682 (5) | 0.7084 (3) | 0.0787 (17) | |
H20 | 0.1593 | 0.2003 | 0.7333 | 0.094* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0430 (14) | 0.0457 (14) | 0.0591 (17) | −0.0026 (11) | 0.0040 (12) | 0.0069 (12) |
O2 | 0.0530 (17) | 0.0562 (17) | 0.092 (2) | −0.0120 (13) | 0.0018 (16) | 0.0252 (16) |
O3 | 0.0191 (12) | 0.0779 (19) | 0.097 (2) | −0.0025 (11) | −0.0024 (13) | 0.0442 (16) |
N1 | 0.0194 (13) | 0.0550 (18) | 0.0431 (17) | 0.0007 (12) | −0.0018 (11) | −0.0013 (13) |
C2 | 0.0246 (16) | 0.053 (2) | 0.0396 (19) | 0.0017 (14) | 0.0008 (13) | 0.0122 (15) |
N3 | 0.0180 (13) | 0.0623 (18) | 0.0494 (18) | 0.0049 (12) | 0.0032 (12) | 0.0202 (15) |
C4 | 0.0201 (15) | 0.064 (2) | 0.059 (2) | −0.0056 (15) | −0.0048 (15) | 0.0344 (19) |
C4A | 0.0258 (16) | 0.055 (2) | 0.050 (2) | −0.0099 (15) | −0.0069 (15) | 0.0240 (17) |
C5 | 0.040 (2) | 0.056 (2) | 0.069 (3) | −0.0214 (18) | −0.0226 (19) | 0.033 (2) |
C6 | 0.055 (2) | 0.047 (2) | 0.077 (3) | −0.0234 (19) | −0.027 (2) | 0.019 (2) |
C7 | 0.051 (2) | 0.046 (2) | 0.064 (3) | −0.0138 (17) | −0.0180 (19) | 0.0059 (18) |
C8 | 0.0353 (18) | 0.049 (2) | 0.053 (2) | −0.0092 (15) | −0.0078 (16) | 0.0025 (17) |
C8A | 0.0268 (16) | 0.0492 (19) | 0.0411 (19) | −0.0095 (14) | −0.0055 (14) | 0.0128 (15) |
C9 | 0.0256 (15) | 0.0421 (17) | 0.0362 (18) | 0.0072 (13) | 0.0037 (12) | 0.0089 (14) |
C10 | 0.0281 (16) | 0.0392 (17) | 0.0398 (18) | 0.0057 (13) | 0.0058 (13) | 0.0060 (14) |
C11 | 0.0331 (17) | 0.0330 (15) | 0.046 (2) | 0.0089 (13) | 0.0101 (14) | 0.0050 (14) |
C12 | 0.064 (2) | 0.0369 (18) | 0.042 (2) | 0.0108 (17) | 0.0086 (18) | −0.0027 (15) |
C13 | 0.076 (3) | 0.047 (2) | 0.048 (2) | 0.015 (2) | 0.005 (2) | −0.0113 (18) |
C14 | 0.051 (2) | 0.047 (2) | 0.063 (3) | 0.0034 (17) | 0.0029 (19) | −0.0081 (19) |
C15 | 0.0380 (18) | 0.0364 (17) | 0.042 (2) | 0.0068 (13) | 0.0013 (15) | 0.0079 (14) |
C16 | 0.0288 (17) | 0.058 (2) | 0.070 (3) | 0.0146 (16) | 0.0111 (17) | 0.028 (2) |
C17 | 0.0269 (15) | 0.0302 (16) | 0.064 (2) | 0.0049 (12) | 0.0127 (15) | 0.0106 (15) |
C18 | 0.098 (3) | 0.0220 (15) | 0.044 (2) | 0.0102 (18) | 0.025 (2) | −0.0029 (15) |
C19 | 0.127 (5) | 0.070 (3) | 0.049 (3) | 0.047 (3) | 0.032 (3) | 0.002 (2) |
C20 | 0.068 (3) | 0.067 (3) | 0.102 (4) | 0.020 (2) | 0.046 (3) | 0.043 (3) |
O1—C14 | 1.369 (5) | C8—H8 | 0.9500 |
O1—C11 | 1.386 (4) | C9—C10 | 1.342 (5) |
O2—C17 | 1.378 (4) | C9—C15 | 1.504 (4) |
O2—C20 | 1.418 (6) | C10—C11 | 1.446 (5) |
O3—C4 | 1.247 (4) | C10—H10 | 0.9500 |
N1—C8A | 1.377 (4) | C11—C12 | 1.366 (5) |
N1—C2 | 1.453 (4) | C12—C13 | 1.441 (6) |
N1—H1 | 0.92 (4) | C12—H12 | 0.9500 |
C2—N3 | 1.491 (4) | C13—C14 | 1.339 (6) |
C2—C9 | 1.524 (5) | C13—H13 | 0.9500 |
C2—H2 | 1.0000 | C14—H14 | 0.9500 |
N3—C4 | 1.367 (5) | C15—H15A | 0.9800 |
N3—C16 | 1.471 (5) | C15—H15B | 0.9800 |
C4—C4A | 1.478 (6) | C15—H15C | 0.9800 |
C4A—C8A | 1.402 (4) | C16—C17 | 1.494 (5) |
C4A—C5 | 1.406 (5) | C16—H16A | 0.9900 |
C5—C6 | 1.376 (6) | C16—H16B | 0.9900 |
C5—H5 | 0.9500 | C17—C18 | 1.365 (5) |
C6—C7 | 1.390 (6) | C18—C19 | 1.437 (6) |
C6—H6 | 0.9500 | C18—H18 | 0.9500 |
C7—C8 | 1.389 (5) | C19—C20 | 1.311 (7) |
C7—H7 | 0.9500 | C19—H19 | 0.9500 |
C8—C8A | 1.400 (5) | C20—H20 | 0.9500 |
C14—O1—C11 | 106.8 (3) | C9—C10—H10 | 116.7 |
C17—O2—C20 | 103.4 (3) | C11—C10—H10 | 116.7 |
C8A—N1—C2 | 120.4 (3) | C12—C11—O1 | 109.1 (3) |
C8A—N1—H1 | 116 (2) | C12—C11—C10 | 136.8 (3) |
C2—N1—H1 | 114 (2) | O1—C11—C10 | 114.1 (3) |
N1—C2—N3 | 108.9 (3) | C11—C12—C13 | 106.6 (3) |
N1—C2—C9 | 109.1 (3) | C11—C12—H12 | 126.7 |
N3—C2—C9 | 111.1 (3) | C13—C12—H12 | 126.7 |
N1—C2—H2 | 109.2 | C14—C13—C12 | 106.5 (4) |
N3—C2—H2 | 109.2 | C14—C13—H13 | 126.7 |
C9—C2—H2 | 109.2 | C12—C13—H13 | 126.7 |
C4—N3—C16 | 117.9 (3) | C13—C14—O1 | 111.0 (4) |
C4—N3—C2 | 122.5 (3) | C13—C14—H14 | 124.5 |
C16—N3—C2 | 116.4 (3) | O1—C14—H14 | 124.5 |
O3—C4—N3 | 121.6 (4) | C9—C15—H15A | 109.5 |
O3—C4—C4A | 121.7 (4) | C9—C15—H15B | 109.5 |
N3—C4—C4A | 116.6 (3) | H15A—C15—H15B | 109.5 |
C8A—C4A—C5 | 120.0 (4) | C9—C15—H15C | 109.5 |
C8A—C4A—C4 | 119.7 (3) | H15A—C15—H15C | 109.5 |
C5—C4A—C4 | 120.2 (3) | H15B—C15—H15C | 109.5 |
C6—C5—C4A | 120.8 (3) | N3—C16—C17 | 113.1 (3) |
C6—C5—H5 | 119.6 | N3—C16—H16A | 109.0 |
C4A—C5—H5 | 119.6 | C17—C16—H16A | 109.0 |
C5—C6—C7 | 119.2 (4) | N3—C16—H16B | 109.0 |
C5—C6—H6 | 120.4 | C17—C16—H16B | 109.0 |
C7—C6—H6 | 120.4 | H16A—C16—H16B | 107.8 |
C8—C7—C6 | 121.1 (4) | C18—C17—O2 | 113.0 (3) |
C8—C7—H7 | 119.4 | C18—C17—C16 | 128.5 (3) |
C6—C7—H7 | 119.4 | O2—C17—C16 | 118.3 (3) |
C7—C8—C8A | 120.2 (3) | C17—C18—C19 | 103.4 (4) |
C7—C8—H8 | 119.9 | C17—C18—H18 | 128.3 |
C8A—C8—H8 | 119.9 | C19—C18—H18 | 128.3 |
N1—C8A—C8 | 121.6 (3) | C20—C19—C18 | 109.5 (4) |
N1—C8A—C4A | 119.5 (3) | C20—C19—H19 | 125.3 |
C8—C8A—C4A | 118.8 (3) | C18—C19—H19 | 125.3 |
C10—C9—C15 | 124.3 (3) | C19—C20—O2 | 110.5 (4) |
C10—C9—C2 | 118.9 (3) | C19—C20—H20 | 124.8 |
C15—C9—C2 | 116.8 (3) | O2—C20—H20 | 124.8 |
C9—C10—C11 | 126.7 (3) | ||
C8A—N1—C2—N3 | 40.4 (4) | N1—C2—C9—C10 | 130.5 (3) |
C8A—N1—C2—C9 | 161.8 (3) | N3—C2—C9—C10 | −109.4 (3) |
N1—C2—N3—C4 | −35.4 (4) | N1—C2—C9—C15 | −49.0 (4) |
C9—C2—N3—C4 | −155.6 (3) | N3—C2—C9—C15 | 71.0 (4) |
N1—C2—N3—C16 | 164.9 (3) | C15—C9—C10—C11 | −1.5 (5) |
C9—C2—N3—C16 | 44.8 (4) | C2—C9—C10—C11 | 179.0 (3) |
C16—N3—C4—O3 | −10.5 (5) | C14—O1—C11—C12 | 0.1 (4) |
C2—N3—C4—O3 | −169.9 (3) | C14—O1—C11—C10 | −180.0 (3) |
C16—N3—C4—C4A | 173.0 (3) | C9—C10—C11—C12 | −9.7 (6) |
C2—N3—C4—C4A | 13.6 (4) | C9—C10—C11—O1 | 170.4 (3) |
O3—C4—C4A—C8A | −169.9 (3) | O1—C11—C12—C13 | 0.1 (4) |
N3—C4—C4A—C8A | 6.7 (4) | C10—C11—C12—C13 | −179.8 (4) |
O3—C4—C4A—C5 | 5.2 (5) | C11—C12—C13—C14 | −0.3 (4) |
N3—C4—C4A—C5 | −178.3 (3) | C12—C13—C14—O1 | 0.4 (4) |
C8A—C4A—C5—C6 | 1.3 (5) | C11—O1—C14—C13 | −0.3 (4) |
C4—C4A—C5—C6 | −173.7 (3) | C4—N3—C16—C17 | 105.9 (4) |
C4A—C5—C6—C7 | −0.5 (6) | C2—N3—C16—C17 | −93.5 (4) |
C5—C6—C7—C8 | −0.4 (6) | C20—O2—C17—C18 | 3.2 (4) |
C6—C7—C8—C8A | 0.6 (6) | C20—O2—C17—C16 | 178.6 (3) |
C2—N1—C8A—C8 | 160.4 (3) | N3—C16—C17—C18 | 125.8 (4) |
C2—N1—C8A—C4A | −24.1 (5) | N3—C16—C17—O2 | −48.8 (4) |
C7—C8—C8A—N1 | 175.7 (3) | O2—C17—C18—C19 | −4.7 (4) |
C7—C8—C8A—C4A | 0.2 (5) | C16—C17—C18—C19 | −179.5 (4) |
C5—C4A—C8A—N1 | −176.7 (3) | C17—C18—C19—C20 | 4.5 (5) |
C4—C4A—C8A—N1 | −1.7 (5) | C18—C19—C20—O2 | −2.8 (6) |
C5—C4A—C8A—C8 | −1.1 (5) | C17—O2—C20—C19 | −0.1 (5) |
C4—C4A—C8A—C8 | 173.9 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O3i | 0.92 (4) | 2.04 (4) | 2.949 (4) | 169 (3) |
Symmetry code: (i) x+1/2, −y+1/2, −z+1. |
Funding information
This work was supported by the Ministry of Education and Science of the Russian Federation (grant No. 4.1154.2017/4.6) (X-ray structural analysis) and by the Russian Foundation for Basic Research (grant Nos. 16–03-00125, INT/RUS/RFBR/P-294 and 17–53-45016) (synthetic part).
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