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Acta Crystallographica Section E: Crystallographic Communications logoLink to Acta Crystallographica Section E: Crystallographic Communications
. 2018 Jun 28;74(Pt 7):1035–1038. doi: 10.1107/S2056989018009003

Crystal structure and Hirshfeld surface analysis of 3,3′,3′′-[(1,3,5-triazine-2,4,6-tri­yl)tris­(­oxy)]tris­(5,5-di­methyl­cyclo­hex-2-en-1-one)

Zeliha Atioğlu a, Mehmet Akkurt b, Flavien A A Toze c,*, Gunay Z Mammadova d, Humay M Panahova e
PMCID: PMC6038646  PMID: 30002911

The three cyclo­hexenone rings of the title compound adopt slightly distorted envelope conformations, with the C atom bearing two methyl groups as the flap atom in each case. In the crystal, mol­ecules are linked via C—H⋯O hydrogen bonds, forming a three-dimensional network.

Keywords: crystal structure; 1,3,5-triazine ring; cyclo­hexenone ring; distorted envelope conformation; hydrogen bonding

Abstract

The three cyclo­hexenone rings of the title compound, C27H33N3O6, adopt slightly distorted envelope conformations, with the C atom bearing two methyl groups as the flap atom in each case. These cyclo­hexenone mean planes form dihedral angles of 87.41 (11), 70.73 (11) and 70.47 (11)° with the 1,3,5-triazine ring, while the dihedral angle between the cyclo­hexenone mean planes are 57.52 (12), 23.75 (12) and 53.21 (12)°. In the crystal, mol­ecules are linked via C—H⋯O hydrogen bonds, forming a three-dimensional network.

Chemical context  

β-Diketones are versatile starting materials in the synthesis of organic and coordination compounds (Mahmudov et al., 2017 ▸; Mahmudov & Pombeiro, 2016 ▸). Usually, the active methyl­ene group of β-diketones is a reaction centre in the organic transformations of this class of compounds (Ma et al., 2017a ▸,b ▸; Gurbanov et al., 2017a ▸,b ▸, 2018 ▸; Borisova et al., 2018 ▸; Jlassi et al., 2018 ▸). In contrast, there are few reports on the reactivity of β-diketones as O-nucleophiles (Yusifov et al., 2013 ▸; Ledenyova et al., 2018 ▸; Vandyshev et al., 2017 ▸; Nasirova et al., 2017 ▸). Herein we found a C—O coupling reaction between cyanuric chloride and dimedone leading to the title compound 3,3′,3′′-[(1,3,5-triazine-2,4,6-tri­yl)tris­(­oxy)]tris­(5,5-di­methyl­cyclo­hex-2-en-1-one) (Fig. 1 ▸).graphic file with name e-74-01035-scheme1.jpg

Figure 1.

Figure 1

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The mol­ecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. H atoms are shown as spheres of arbitrary radius.

Structural commentary  

In the title compound, the cyclo­hexenone rings A (C4–C8/C11), B (C12–C16/C19) and C (C20–C22/C25–C27) adopt distorted envelope conformations, with flap atoms C8, C16 and C22, respectively [the puckering parameters are: for A, Q T = 0.436 (3) Å, θ = 130.8 (4), φ = 43.3 (5)°, for B, Q T = 0.449 (3) Å, θ = 131.0 (4)°, φ = 46.2 (4)° and for C, Q T = 0.451 (3) Å, θ = 123.6 (4)°, φ = 298.6 (4)°]. The dihedral angle between the cyclo­hexenone rings are A/B = 57.52 (12), A/C = 23.75 (12) and B/C =53.21 (12)°. The dihedral angle between the 1,3,5-triazine ring (C1/N1/C2/N2/C3/N3) and cyclo­hexenone rings A, B and C are 87.41 (11), 70.73 (11) and 70.47 (11)°, respectively.

The values of the geometric parameters are normal and are comparable to those observed in similar compounds such as 2,2′-[(3-bromo-4-hy­droxy-5-meth­oxy­phen­yl)methyl­idene]bis(3-hy­droxy-5,5-di­methyl­cyclo­hex-2-en-1-one) (Sughanya & Sureshbabu, 2012 ▸) and 3-hy­droxy-2-[(4-hy­droxy-3,5-di­meth­oxy­phen­yl)(2-hy­droxy-4,4-dimethyl-6-oxo­cyclo­hex-1-en-1-yl)meth­yl]-5,5-di­methyl­cyclo­hex-2-en-1-one (Yang et al., 2011 ▸).

Supra­molecular features  

In the crystal, mol­ecules are linked by C—H⋯O hydrogen bonds, forming a three-dimensional network (Table 1 ▸; Fig. 2 ▸). The mol­ecules are further linked by weak C—O⋯π inter­actions between the carbonyl groups, and the centroids (Cg1) of the 1,3,5-triazine rings of neighbouring mol­ecules: C14—O5 = 1.213 (3), O5⋯Cg11iii = 3.013 (2), C14⋯Cg1iii = 3.892 (3) Å, C14—O5⋯Cg1i = 129.0 (2)°; C26—O6 = 1.213 (3), O6⋯Cg1ii = 3.126 (2), C26⋯Cg1ii = 3.899 (3) Å, C26—O6⋯Cg1ii = 121.4 (2)°; symmetry codes: (iii) x, 1 + y, z; (ii) x, −1 + y, z]. No C—H⋯π inter­actions or π–π stacking inter­actions are observed in the crystal structure.

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C5—H5A⋯O4i 0.93 2.59 3.447 (3) 153
C19—H19A⋯O5ii 0.97 2.60 3.532 (3) 162
C21—H21B⋯O6iii 0.97 2.57 3.399 (3) 143
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Symmetry codes: (i) Inline graphic; (ii) Inline graphic; (iii) Inline graphic.

Figure 2.

Figure 2

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A view of the inter­molecular C—H⋯O hydrogen bonds (Table 1 ▸) in the title compound.

Hiershfeld surface analysis  

Hirshfeld surfaces and fingerprint plots were generated for the title compound based on the crystallographic information file (CIF) using CrystalExplorer (McKinnon et al., 2007 ▸). Hirshfeld surfaces enable the visualization of inter­molecular inter­actions by different colors and color intensity, representing short or long contacts and indicating the relative strength of the inter­actions. Fig. 3 ▸ shows the Hirshfeld surface of the title compound mapped over d norm(−0.16 to 1.25 a.u.). It is evident from the bright-red spots appearing near the oxygen atoms in this figure that these atoms play a significant role in the mol­ecular packing. The red points, which represent closer contacts and negative d norm values on the surface, correspond to the C—H⋯O inter­actions.

Figure 3.

Figure 3

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Hirshfeld surface of the title compound mapped over d norm.

The percentage contributions of various contacts to the total Hirshfeld surface are shown in the two-dimensional fingerprint plots in Fig. 4 ▸. The H⋯H inter­actions appear in the middle of the scattered points in the two-dimensional fingerprint plots with an overall contribution to the Hirshfeld surface of 57.5% (Fig. 4 ▸ b). The contribution (25.9%) from the O⋯H/H⋯O contacts, corresponding to C—H⋯O inter­actions, is represented by a pair of sharp spikes characteristic of a strong hydrogen-bonding inter­action (Fig. 4 ▸ c). The contribution of the inter­molecular N⋯H/H⋯N contacts to the Hirshfeld surfaces is 6.3% (Fig. 4 ▸ d). The small percentage contributions from the other different inter­atomic contacts are as follows: C⋯O/O⋯C (3.8%), C⋯H/H⋯C (3.3%), N⋯O/O⋯N (2.1%), O⋯O (0.9%) and C⋯N/N⋯C (0.2%). The large number of H⋯H, H⋯O/O⋯H and H⋯N/N⋯H inter­actions suggest that van der Waals inter­actions and hydrogen bonding play the major roles in the crystal packing (Hathwar et al., 2015 ▸). The three-dimensional shape-index surface of the title compound is shown in Fig. 5 ▸.

Figure 4.

Figure 4

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The two-dimensional fingerprint plots of the title compound, showing (a) all inter­actions, and delineated into (b) H⋯H, (c) O⋯H/ H⋯O, (d) H⋯N/N⋯H, (e) C⋯O/O⋯C and (f) C⋯H/H⋯C inter­actions [d e and d i represent the distances from a point on the Hirshfeld surface to the nearest atoms outside (external) and inside (inter­nal) the surface, respectively].

Figure 5.

Figure 5

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View of the three-dimensional Hirshfeld surface of the title complex plotted over shape-index.

Synthesis and crystallization  

1.40 g (10 mmol) dimedone was added to 30 mL of an aqueous solution of KOH (0.56 g, 10 mmol) and the solution was stirred for 5 min at room temperature. Cyanuric chloride (0.61 g, 3.3 mmol) was added to this alkali solution of dimedone in 10 portions under stirring for 10 min. After 2 h, the formed white precipitate of the product was filtered off and was recrystallized from methanol. Yield 84% (based on cyanuric chloride), white powder, soluble in DMSO, ethanol and di­methyl­formamide and insoluble in non-polar solvents. Analysis calculated for C27H33N3O6 (M r = 495.58): C, 65.44; H, 6.71; N, 8.48. Found: C, 65.40; H, 6.65; N, 8.43%. MS (ESI) (positive ion mode): m/z: 496.73 [M + H]+. 1H NMR (DMSO-d6): δ 1.01 (18H, 6CH3), 1.90 and 2.34 (12H, 6CH2), 5.80 (3H, C—H). 13C{1H} (DMSO-d6): δ 27.80 (6CH3), 44.56 (3CH2), 48.12 (3CH2), 124.31 (3CH), 167.72 (3C=C—O), 176.23 (3C—O) and 196.58 (3C=O).

Refinement details  

Crystal data, data collection and structure refinement details are summarized in Table 2 ▸. All H atoms were fixed geom­etrically and allowed to ride on the attached non-H atoms, with C —H = 0.93–0.97 Å, and with U iso(H) = 1.5U eq(C) for methyl H atoms and 1.2U eq(C) for all other atoms.

Table 2. Experimental details.

Crystal data
Chemical formula C27H33N3O6
M r 495.56
Crystal system, space group Monoclinic, P21/c
Temperature (K) 296
a, b, c (Å) 18.084 (2), 7.3858 (10), 20.614 (3)
β (°) 104.725 (5)
V (Å3) 2662.9 (6)
Z 4
Radiation type Mo Kα
μ (mm−1) 0.09
Crystal size (mm) 0.34 × 0.19 × 0.14
 
Data collection
Diffractometer Bruker APEXII CCD
Absorption correction Multi-scan (SADABS; Sheldrick, 2008 ▸)
T min, T max 0.964, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections 30340, 5064, 2847
R int 0.100
(sin θ/λ)max (Å−1) 0.612
 
Refinement
R[F 2 > 2σ(F 2)], wR(F 2), S 0.053, 0.159, 1.01
No. of reflections 5064
No. of parameters 331
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.17, −0.24
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Computer programs: APEX2 and SAINT (Bruker, 2007 ▸), SHELXS97 (Sheldrick, 2008 ▸), SHELXL2014 (Sheldrick, 2015 ▸), ORTEP-3 for Windows (Farrugia, 2012 ▸) and PLATON (Spek, 2003 ▸).

Supplementary Material

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989018009003/zp2030sup1.cif

e-74-01035-sup1.cif (933.3KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989018009003/zp2030Isup2.hkl

e-74-01035-Isup2.hkl (403.1KB, hkl)
Click here for additional data file. (5.1KB, cml)

Supporting information file. DOI: 10.1107/S2056989018009003/zp2030Isup3.cml

CCDC reference: 1850649

Additional supporting information: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

Crystal data

C27H33N3O6 F(000) = 1056
Mr = 495.56 Dx = 1.236 Mg m−3
Monoclinic, P21/c Mo Kα radiation, λ = 0.71073 Å
a = 18.084 (2) Å Cell parameters from 6177 reflections
b = 7.3858 (10) Å θ = 2.3–25.6°
c = 20.614 (3) Å µ = 0.09 mm−1
β = 104.725 (5)° T = 296 K
V = 2662.9 (6) Å3 Block, colourless
Z = 4 0.34 × 0.19 × 0.14 mm
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Data collection

Bruker APEXII CCD diffractometer 2847 reflections with I > 2σ(I)
φ and ω scans Rint = 0.100
Absorption correction: multi-scan (SADABS; Sheldrick, 2008) θmax = 25.8°, θmin = 2.6°
Tmin = 0.964, Tmax = 0.982 h = −22→22
30340 measured reflections k = −9→9
5064 independent reflections l = −25→25
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Refinement

Refinement on F2 0 restraints
Least-squares matrix: full Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.053 H-atom parameters constrained
wR(F2) = 0.159 w = 1/[σ2(Fo2) + (0.0858P)2 + 0.0315P] where P = (Fo2 + 2Fc2)/3
S = 1.01 (Δ/σ)max < 0.001
5064 reflections Δρmax = 0.17 e Å−3
331 parameters Δρmin = −0.24 e Å−3
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Special details

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.
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
C1 0.24163 (12) 0.5010 (3) 0.78577 (11) 0.0352 (5)
C2 0.13024 (12) 0.6221 (3) 0.74190 (12) 0.0375 (6)
C3 0.16639 (12) 0.3837 (3) 0.69484 (12) 0.0369 (5)
C4 0.36056 (12) 0.3650 (3) 0.83435 (12) 0.0394 (6)
C5 0.41371 (13) 0.3863 (3) 0.80154 (13) 0.0474 (6)
H5A 0.414886 0.490563 0.776511 0.057*
C6 0.47069 (14) 0.2444 (3) 0.80498 (14) 0.0497 (7)
C7 0.47343 (13) 0.0961 (4) 0.85502 (14) 0.0540 (7)
H7A 0.504492 0.135622 0.898256 0.065*
H7B 0.498106 −0.008829 0.841457 0.065*
C8 0.39470 (13) 0.0401 (3) 0.86274 (13) 0.0457 (6)
C9 0.34874 (15) −0.0466 (4) 0.79846 (14) 0.0578 (7)
H9A 0.300597 −0.087701 0.804551 0.087*
H9B 0.376563 −0.147656 0.787322 0.087*
H9C 0.339957 0.040625 0.762789 0.087*
C10 0.40348 (17) −0.0952 (4) 0.91991 (15) 0.0721 (9)
H10A 0.353844 −0.130632 0.924139 0.108*
H10B 0.431630 −0.040324 0.960993 0.108*
H10C 0.430498 −0.199987 0.910640 0.108*
C11 0.35337 (14) 0.2092 (3) 0.87747 (13) 0.0468 (6)
H11A 0.299616 0.181148 0.871222 0.056*
H11B 0.373899 0.242978 0.924046 0.056*
C12 0.08311 (12) 0.8590 (3) 0.79663 (12) 0.0410 (6)
C13 0.09560 (14) 1.0324 (3) 0.79119 (13) 0.0470 (6)
H13A 0.102783 1.077750 0.751140 0.056*
C14 0.09837 (14) 1.1550 (3) 0.84702 (13) 0.0491 (7)
C15 0.07422 (14) 1.0778 (3) 0.90568 (13) 0.0478 (6)
H15A 0.019044 1.086247 0.897016 0.057*
H15B 0.096344 1.150036 0.945123 0.057*
C16 0.09812 (14) 0.8803 (3) 0.92030 (13) 0.0484 (7)
C17 0.0646 (2) 0.8065 (4) 0.97584 (16) 0.0761 (9)
H17A 0.010036 0.819671 0.962993 0.114*
H17B 0.085256 0.872627 1.016510 0.114*
H17C 0.077532 0.680699 0.982980 0.114*
C18 0.18568 (15) 0.8686 (4) 0.94248 (15) 0.0667 (8)
H18A 0.200952 0.743947 0.948294 0.100*
H18B 0.203935 0.931994 0.984139 0.100*
H18C 0.206908 0.922596 0.908869 0.100*
C19 0.06780 (14) 0.7700 (3) 0.85618 (13) 0.0465 (6)
H19A 0.091580 0.651387 0.861718 0.056*
H19B 0.013106 0.753238 0.848962 0.056*
C20 0.20769 (13) 0.1412 (3) 0.63687 (11) 0.0403 (6)
C21 0.27721 (14) 0.2252 (3) 0.62347 (13) 0.0455 (6)
H21A 0.314724 0.246081 0.665677 0.055*
H21B 0.263836 0.341455 0.601772 0.055*
C22 0.31233 (14) 0.1041 (3) 0.57862 (12) 0.0449 (6)
C23 0.26205 (16) 0.1060 (4) 0.50692 (13) 0.0592 (7)
H23A 0.283448 0.026626 0.479581 0.089*
H23B 0.259545 0.226814 0.489336 0.089*
H23C 0.211536 0.065647 0.506731 0.089*
C24 0.39175 (16) 0.1760 (4) 0.57940 (16) 0.0717 (9)
H24A 0.414793 0.098988 0.552510 0.108*
H24B 0.422971 0.177397 0.624662 0.108*
H24C 0.387400 0.296629 0.561525 0.108*
C25 0.31926 (15) −0.0878 (3) 0.60713 (14) 0.0527 (7)
H25A 0.334273 −0.167835 0.575397 0.063*
H25B 0.360003 −0.089323 0.648135 0.063*
C26 0.24829 (15) −0.1627 (4) 0.62219 (12) 0.0497 (6)
C27 0.19336 (14) −0.0336 (3) 0.63526 (13) 0.0471 (6)
H27A 0.147559 −0.074862 0.642567 0.057*
N1 0.19417 (10) 0.6328 (2) 0.78932 (9) 0.0374 (5)
N2 0.11151 (10) 0.5028 (3) 0.69217 (10) 0.0414 (5)
N3 0.23251 (10) 0.3701 (2) 0.74050 (9) 0.0363 (5)
O1 0.30770 (9) 0.5048 (2) 0.83405 (8) 0.0444 (4)
O2 0.07577 (9) 0.7480 (2) 0.73984 (8) 0.0467 (4)
O3 0.14991 (9) 0.2578 (2) 0.64567 (9) 0.0478 (5)
O4 0.51468 (12) 0.2482 (3) 0.76883 (12) 0.0776 (7)
O5 0.11854 (13) 1.3113 (2) 0.84562 (11) 0.0753 (6)
O6 0.23846 (13) −0.3247 (3) 0.62492 (11) 0.0795 (7)
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
C1 0.0343 (12) 0.0306 (13) 0.0423 (14) −0.0016 (10) 0.0130 (11) −0.0023 (11)
C2 0.0371 (13) 0.0294 (12) 0.0496 (15) 0.0020 (10) 0.0180 (11) 0.0018 (11)
C3 0.0379 (13) 0.0309 (12) 0.0444 (14) −0.0025 (10) 0.0151 (11) −0.0044 (11)
C4 0.0342 (12) 0.0362 (13) 0.0464 (14) 0.0018 (10) 0.0078 (11) −0.0100 (11)
C5 0.0455 (14) 0.0382 (14) 0.0624 (17) −0.0032 (11) 0.0208 (13) 0.0002 (13)
C6 0.0394 (14) 0.0464 (15) 0.0690 (19) −0.0048 (11) 0.0239 (13) −0.0024 (13)
C7 0.0401 (14) 0.0529 (17) 0.0695 (19) 0.0102 (12) 0.0146 (13) 0.0069 (14)
C8 0.0415 (13) 0.0463 (15) 0.0517 (16) 0.0045 (11) 0.0161 (12) 0.0071 (13)
C9 0.0623 (17) 0.0462 (16) 0.0675 (19) −0.0053 (13) 0.0213 (15) −0.0026 (14)
C10 0.077 (2) 0.071 (2) 0.073 (2) 0.0139 (16) 0.0281 (17) 0.0241 (17)
C11 0.0465 (14) 0.0543 (16) 0.0436 (15) 0.0030 (12) 0.0189 (12) −0.0003 (13)
C12 0.0340 (12) 0.0381 (14) 0.0527 (16) 0.0107 (10) 0.0145 (11) −0.0023 (12)
C13 0.0558 (15) 0.0336 (15) 0.0558 (16) 0.0060 (11) 0.0221 (13) 0.0045 (12)
C14 0.0538 (15) 0.0309 (14) 0.0642 (18) 0.0058 (12) 0.0181 (13) 0.0019 (13)
C15 0.0491 (14) 0.0438 (15) 0.0521 (16) 0.0033 (12) 0.0156 (12) −0.0088 (12)
C16 0.0491 (14) 0.0451 (15) 0.0558 (17) 0.0055 (11) 0.0219 (12) 0.0072 (13)
C17 0.096 (2) 0.072 (2) 0.072 (2) 0.0067 (18) 0.0417 (18) 0.0139 (17)
C18 0.0567 (17) 0.0641 (19) 0.074 (2) 0.0107 (14) 0.0062 (15) 0.0113 (16)
C19 0.0422 (13) 0.0325 (13) 0.0701 (18) 0.0037 (10) 0.0236 (13) 0.0038 (13)
C20 0.0452 (13) 0.0405 (15) 0.0355 (13) 0.0040 (11) 0.0108 (10) −0.0076 (11)
C21 0.0522 (15) 0.0371 (14) 0.0494 (15) −0.0047 (11) 0.0169 (12) −0.0100 (12)
C22 0.0524 (15) 0.0406 (14) 0.0459 (15) −0.0035 (11) 0.0202 (12) −0.0036 (12)
C23 0.0763 (19) 0.0613 (18) 0.0448 (16) −0.0099 (14) 0.0244 (14) −0.0032 (14)
C24 0.0663 (19) 0.078 (2) 0.080 (2) −0.0166 (16) 0.0360 (17) −0.0172 (18)
C25 0.0600 (16) 0.0475 (16) 0.0561 (17) 0.0085 (13) 0.0246 (13) −0.0044 (13)
C26 0.0709 (17) 0.0384 (16) 0.0431 (15) 0.0048 (13) 0.0204 (13) 0.0027 (12)
C27 0.0543 (15) 0.0412 (15) 0.0505 (16) −0.0026 (12) 0.0217 (13) −0.0038 (12)
N1 0.0361 (10) 0.0293 (10) 0.0494 (12) 0.0002 (8) 0.0156 (9) −0.0052 (9)
N2 0.0357 (11) 0.0381 (11) 0.0511 (13) 0.0028 (8) 0.0126 (9) −0.0059 (10)
N3 0.0383 (10) 0.0302 (10) 0.0415 (11) 0.0017 (8) 0.0120 (9) −0.0048 (9)
O1 0.0398 (9) 0.0407 (10) 0.0508 (10) 0.0071 (7) 0.0076 (8) −0.0120 (8)
O2 0.0436 (9) 0.0396 (9) 0.0565 (11) 0.0116 (7) 0.0117 (8) −0.0066 (8)
O3 0.0429 (9) 0.0444 (10) 0.0539 (11) 0.0049 (7) 0.0083 (8) −0.0169 (8)
O4 0.0715 (13) 0.0625 (13) 0.1195 (19) 0.0047 (10) 0.0626 (14) 0.0057 (12)
O5 0.1122 (17) 0.0341 (11) 0.0883 (16) −0.0123 (11) 0.0416 (13) −0.0049 (10)
O6 0.1165 (17) 0.0338 (12) 0.1037 (17) 0.0018 (11) 0.0566 (14) 0.0050 (11)
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Geometric parameters (Å, º)

C1—N1 1.312 (3) C14—C15 1.499 (4)
C1—N3 1.325 (3) C15—C16 1.529 (4)
C1—O1 1.347 (3) C15—H15A 0.9700
C2—N1 1.313 (3) C15—H15B 0.9700
C2—N2 1.329 (3) C16—C17 1.526 (4)
C2—O2 1.348 (3) C16—C19 1.530 (4)
C3—N2 1.317 (3) C16—C18 1.535 (4)
C3—N3 1.324 (3) C17—H17A 0.9600
C3—O3 1.351 (3) C17—H17B 0.9600
C4—C5 1.318 (3) C17—H17C 0.9600
C4—O1 1.406 (3) C18—H18A 0.9600
C4—C11 1.480 (3) C18—H18B 0.9600
C5—C6 1.459 (3) C18—H18C 0.9600
C5—H5A 0.9300 C19—H19A 0.9700
C6—O4 1.221 (3) C19—H19B 0.9700
C6—C7 1.497 (4) C20—C27 1.316 (3)
C7—C8 1.529 (3) C20—O3 1.401 (3)
C7—H7A 0.9700 C20—C21 1.489 (3)
C7—H7B 0.9700 C21—C22 1.535 (3)
C8—C9 1.515 (4) C21—H21A 0.9700
C8—C10 1.522 (4) C21—H21B 0.9700
C8—C11 1.525 (3) C22—C23 1.526 (4)
C9—H9A 0.9600 C22—C24 1.527 (4)
C9—H9B 0.9600 C22—C25 1.528 (3)
C9—H9C 0.9600 C23—H23A 0.9600
C10—H10A 0.9600 C23—H23B 0.9600
C10—H10B 0.9600 C23—H23C 0.9600
C10—H10C 0.9600 C24—H24A 0.9600
C11—H11A 0.9700 C24—H24B 0.9600
C11—H11B 0.9700 C24—H24C 0.9600
C12—C13 1.310 (3) C25—C26 1.501 (4)
C12—O2 1.407 (3) C25—H25A 0.9700
C12—C19 1.479 (3) C25—H25B 0.9700
C13—C14 1.455 (3) C26—O6 1.213 (3)
C13—H13A 0.9300 C26—C27 1.451 (3)
C14—O5 1.213 (3) C27—H27A 0.9300
N1—C1—N3 127.9 (2) C17—C16—C18 109.4 (2)
N1—C1—O1 114.44 (19) C15—C16—C18 109.3 (2)
N3—C1—O1 117.62 (19) C19—C16—C18 110.1 (2)
N1—C2—N2 128.16 (19) C16—C17—H17A 109.5
N1—C2—O2 118.7 (2) C16—C17—H17B 109.5
N2—C2—O2 113.10 (19) H17A—C17—H17B 109.5
N2—C3—N3 127.9 (2) C16—C17—H17C 109.5
N2—C3—O3 114.07 (19) H17A—C17—H17C 109.5
N3—C3—O3 117.93 (19) H17B—C17—H17C 109.5
C5—C4—O1 119.6 (2) C16—C18—H18A 109.5
C5—C4—C11 126.0 (2) C16—C18—H18B 109.5
O1—C4—C11 114.2 (2) H18A—C18—H18B 109.5
C4—C5—C6 119.2 (2) C16—C18—H18C 109.5
C4—C5—H5A 120.4 H18A—C18—H18C 109.5
C6—C5—H5A 120.4 H18B—C18—H18C 109.5
O4—C6—C5 121.0 (2) C12—C19—C16 112.3 (2)
O4—C6—C7 121.7 (2) C12—C19—H19A 109.2
C5—C6—C7 117.3 (2) C16—C19—H19A 109.2
C6—C7—C8 113.6 (2) C12—C19—H19B 109.2
C6—C7—H7A 108.8 C16—C19—H19B 109.2
C8—C7—H7A 108.8 H19A—C19—H19B 107.9
C6—C7—H7B 108.8 C27—C20—O3 117.3 (2)
C8—C7—H7B 108.8 C27—C20—C21 125.0 (2)
H7A—C7—H7B 107.7 O3—C20—C21 117.4 (2)
C9—C8—C10 109.0 (2) C20—C21—C22 111.55 (19)
C9—C8—C11 109.4 (2) C20—C21—H21A 109.3
C10—C8—C11 110.1 (2) C22—C21—H21A 109.3
C9—C8—C7 110.0 (2) C20—C21—H21B 109.3
C10—C8—C7 110.0 (2) C22—C21—H21B 109.3
C11—C8—C7 108.4 (2) H21A—C21—H21B 108.0
C8—C9—H9A 109.5 C23—C22—C24 109.5 (2)
C8—C9—H9B 109.5 C23—C22—C25 110.6 (2)
H9A—C9—H9B 109.5 C24—C22—C25 109.5 (2)
C8—C9—H9C 109.5 C23—C22—C21 110.0 (2)
H9A—C9—H9C 109.5 C24—C22—C21 108.9 (2)
H9B—C9—H9C 109.5 C25—C22—C21 108.4 (2)
C8—C10—H10A 109.5 C22—C23—H23A 109.5
C8—C10—H10B 109.5 C22—C23—H23B 109.5
H10A—C10—H10B 109.5 H23A—C23—H23B 109.5
C8—C10—H10C 109.5 C22—C23—H23C 109.5
H10A—C10—H10C 109.5 H23A—C23—H23C 109.5
H10B—C10—H10C 109.5 H23B—C23—H23C 109.5
C4—C11—C8 113.3 (2) C22—C24—H24A 109.5
C4—C11—H11A 108.9 C22—C24—H24B 109.5
C8—C11—H11A 108.9 H24A—C24—H24B 109.5
C4—C11—H11B 108.9 C22—C24—H24C 109.5
C8—C11—H11B 108.9 H24A—C24—H24C 109.5
H11A—C11—H11B 107.7 H24B—C24—H24C 109.5
C13—C12—O2 118.7 (2) C26—C25—C22 115.5 (2)
C13—C12—C19 125.3 (2) C26—C25—H25A 108.4
O2—C12—C19 115.7 (2) C22—C25—H25A 108.4
C12—C13—C14 120.8 (2) C26—C25—H25B 108.4
C12—C13—H13A 119.6 C22—C25—H25B 108.4
C14—C13—H13A 119.6 H25A—C25—H25B 107.5
O5—C14—C13 121.6 (2) O6—C26—C27 121.6 (3)
O5—C14—C15 122.2 (2) O6—C26—C25 121.1 (2)
C13—C14—C15 116.3 (2) C27—C26—C25 117.3 (2)
C14—C15—C16 113.4 (2) C20—C27—C26 120.7 (2)
C14—C15—H15A 108.9 C20—C27—H27A 119.7
C16—C15—H15A 108.9 C26—C27—H27A 119.7
C14—C15—H15B 108.9 C1—N1—C2 112.26 (19)
C16—C15—H15B 108.9 C3—N2—C2 111.66 (19)
H15A—C15—H15B 107.7 C3—N3—C1 111.95 (18)
C17—C16—C15 110.0 (2) C1—O1—C4 117.56 (17)
C17—C16—C19 109.6 (2) C2—O2—C12 117.53 (18)
C15—C16—C19 108.4 (2) C3—O3—C20 119.36 (17)
O1—C4—C5—C6 176.9 (2) C23—C22—C25—C26 −70.8 (3)
C11—C4—C5—C6 1.9 (4) C24—C22—C25—C26 168.5 (2)
C4—C5—C6—O4 170.7 (3) C21—C22—C25—C26 49.9 (3)
C4—C5—C6—C7 −10.1 (4) C22—C25—C26—O6 157.2 (2)
O4—C6—C7—C8 −143.6 (3) C22—C25—C26—C27 −24.7 (3)
C5—C6—C7—C8 37.1 (3) O3—C20—C27—C26 176.2 (2)
C6—C7—C8—C9 66.4 (3) C21—C20—C27—C26 2.5 (4)
C6—C7—C8—C10 −173.6 (2) O6—C26—C27—C20 175.0 (3)
C6—C7—C8—C11 −53.2 (3) C25—C26—C27—C20 −3.2 (4)
C5—C4—C11—C8 −20.7 (3) N3—C1—N1—C2 2.1 (3)
O1—C4—C11—C8 164.03 (19) O1—C1—N1—C2 −179.09 (18)
C9—C8—C11—C4 −75.6 (3) N2—C2—N1—C1 −2.9 (3)
C10—C8—C11—C4 164.6 (2) O2—C2—N1—C1 179.37 (19)
C7—C8—C11—C4 44.3 (3) N3—C3—N2—C2 2.2 (3)
O2—C12—C13—C14 175.7 (2) O3—C3—N2—C2 179.37 (19)
C19—C12—C13—C14 2.5 (4) N1—C2—N2—C3 1.0 (3)
C12—C13—C14—O5 171.3 (2) O2—C2—N2—C3 178.84 (19)
C12—C13—C14—C15 −9.3 (4) N2—C3—N3—C1 −2.8 (3)
O5—C14—C15—C16 −144.1 (3) O3—C3—N3—C1 −179.92 (19)
C13—C14—C15—C16 36.5 (3) N1—C1—N3—C3 0.4 (3)
C14—C15—C16—C17 −174.3 (2) O1—C1—N3—C3 −178.33 (19)
C14—C15—C16—C19 −54.5 (3) N1—C1—O1—C4 178.46 (19)
C14—C15—C16—C18 65.5 (3) N3—C1—O1—C4 −2.6 (3)
C13—C12—C19—C16 −22.7 (3) C5—C4—O1—C1 91.5 (3)
O2—C12—C19—C16 163.90 (18) C11—C4—O1—C1 −92.9 (2)
C17—C16—C19—C12 166.6 (2) N1—C2—O2—C12 −13.8 (3)
C15—C16—C19—C12 46.6 (3) N2—C2—O2—C12 168.13 (19)
C18—C16—C19—C12 −73.0 (3) C13—C12—O2—C2 113.9 (2)
C27—C20—C21—C22 25.3 (3) C19—C12—O2—C2 −72.3 (2)
O3—C20—C21—C22 −148.4 (2) N2—C3—O3—C20 170.2 (2)
C20—C21—C22—C23 72.3 (3) N3—C3—O3—C20 −12.3 (3)
C20—C21—C22—C24 −167.7 (2) C27—C20—O3—C3 127.7 (2)
C20—C21—C22—C25 −48.7 (3) C21—C20—O3—C3 −58.1 (3)
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Hydrogen-bond geometry (Å, º)

D—H···A D—H H···A D···A D—H···A
C5—H5A···O4i 0.93 2.59 3.447 (3) 153
C19—H19A···O5ii 0.97 2.60 3.532 (3) 162
C21—H21B···O6iii 0.97 2.57 3.399 (3) 143
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Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) x, y−1, z; (iii) x, y+1, z.

Funding Statement

This work was funded by Baki Dövlet Universiteti grant .

References

  1. Borisova, K. K., Nikitina, E. V., Novikov, R. A., Khrustalev, V. N., Dorovatovskii, P. V., Zubavichus, Y. V., Kuznetsov, M. L., Zaytsev, V. P., Varlamov, A. V. & Zubkov, F. I. (2018). Chem. Commun. 54, 2850–2853. [DOI] [PubMed]
  2. Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
  3. Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.
  4. Gurbanov, A. V., Mahmoudi, G., Guedes da Silva, M. F. C., Zubkov, F. I., Mahmudov, K. T. & Pombeiro, A. J. L. (2018). Inorg. Chim. Acta, 471, 130–136.
  5. Gurbanov, A. V., Mahmudov, K. T., Kopylovich, M. N., Guedes da Silva, F. M., Sutradhar, M., Guseinov, F. I., Zubkov, F. I., Maharramov, A. M. & Pombeiro, A. J. L. (2017a). Dyes Pigments, 138, 107–111.
  6. Gurbanov, A. V., Mahmudov, K. T., Sutradhar, M., Guedes da Silva, F. C., Mahmudov, T. A., Guseinov, F. I., Zubkov, F. I., Maharramov, A. M. & Pombeiro, A. J. L. (2017b). J. Organomet. Chem. 834, 22–27.
  7. Hathwar, V. R., Sist, M., Jørgensen, M. R. V., Mamakhel, A. H., Wang, X., Hoffmann, C. M., Sugimoto, K., Overgaard, J. & Iversen, B. B. (2015). IUCrJ, 2, 563–574. [DOI] [PMC free article] [PubMed]
  8. Jlassi, R., Ribeiro, A. P. C., Alegria, E. C. B. A., Naïli, H., Tiago, G. A. O., Rüffer, T., Lang, H., Zubkov, F. I., Pombeiro, A. J. L. & Rekik, W. (2018). Inorg. Chim. Acta, 471, 658–663.
  9. Ledenyova, I. V., Falaleev, A. V., Shikhaliev, Kh. S., Ryzhkova, E. A. & Zubkov, F. I. (2018). Russ. J. Gen. Chem. 88, 73–79.
  10. Ma, Z., Gurbanov, A. V., Maharramov, A. M., Guseinov, F. I., Kopylovich, M. N., Zubkov, F. I., Mahmudov, K. T. & Pombeiro, A. J. L. (2017a). J. Mol. Catal. A Chem. 426, 526–533.
  11. Ma, Z., Gurbanov, A. V., Sutradhar, M., Kopylovich, M. N., Mahmudov, K. T., Maharramov, A. M., Guseinov, F. I., Zubkov, F. I. & Pombeiro, A. J. L. (2017b). J. Mol. Catal. A Chem. 428, 17–23.
  12. Mahmudov, K. T., Kopylovich, M. N., Guedes da Silva, M. F. C. & Pombeiro, A. J. L. (2017). Coord. Chem. Rev. 345, 54–72.
  13. Mahmudov, K. T. & Pombeiro, A. J. L. (2016). Chem. Eur. J. 22, 16356–16398. [DOI] [PubMed]
  14. McKinnon, J. J., Jayatilaka, D. & Spackman, M. A. (2007). Chem. Commun. pp. 3814–3816. [DOI] [PubMed]
  15. Nasirova, D. K., Malkova, A. V., Polyanskii, K. B., Yankina, K. Y., Amoyaw, P. N.-A., Kolesnik, I. A., Kletskov, A. V., Godovikov, I. A., Nikitina, E. V. & Zubkov, F. I. (2017). Tetrahedron Lett. 58, 4384–4387.
  16. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
  17. Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8.
  18. Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13.
  19. Sughanya, V. & Sureshbabu, N. (2012). Acta Cryst. E68, o2875–o2876. [DOI] [PMC free article] [PubMed]
  20. Vandyshev, D. Y., Shikhaliev, K. S., Potapov, A. Y., Krysin, M. Y., Zubkov, F. I. & Sapronova, L. V. (2017). Beilstein J. Org. Chem. 13, 2561–2568. [DOI] [PMC free article] [PubMed]
  21. Yang, X.-H., Zhou, Y.-H., Zhang, M. & Hu, L.-H. (2011). Acta Cryst. E67, o492. [DOI] [PMC free article] [PubMed]
  22. Yusifov, N. N., Ismayilov, V. M., Sadigova, N. D., Kopylovich, M. N. & Mahmudov, K. T. (2013). Mendeleev Commun. 23, 292–293.

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989018009003/zp2030sup1.cif

e-74-01035-sup1.cif (933.3KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989018009003/zp2030Isup2.hkl

e-74-01035-Isup2.hkl (403.1KB, hkl)
Click here for additional data file. (5.1KB, cml)

Supporting information file. DOI: 10.1107/S2056989018009003/zp2030Isup3.cml

CCDC reference: 1850649

Additional supporting information: crystallographic information; 3D view; checkCIF report

Articles from Acta Crystallographica Section E: Crystallographic Communications are provided here courtesy of International Union of Crystallography

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