research communications
Crystal structures and Hirshfeld surface analyses of (E)-1-[1-(4-tert-butylphenyl)-2,2-dichloroethenyl]-2-phenyldiazene, (E)-1-[1-(4-tert-butylphenyl)-2,2-dichloroethenyl]-2-(4-methylphenyl)diazene, (E)-1-[1-(4-tert-butylphenyl)-2,2-dichloroethenyl]-2-(4-methoxyphenyl)diazene and (E)-1-[1-(4-tert-butylphenyl)-2,2-dichloroethenyl]-2-(3-methylphenyl)diazene
aOrganic Chemistry Department, Baku State University, Z. Khalilov str. 23, AZ 1148 Baku, Azerbaijan, bDepartment of Engineering and Applied Sciences, Azerbaijan State University of Economics, M. Mukhtarov 194, Baku AZ1001, Azerbaijan, cPeoples' Friendship University of Russia (RUDN University), Miklukho-Maklay St. 6, Moscow, 117198, Russian Federation, dN. D. Zelinsky Institute of Organic Chemistry RAS, Leninsky Prosp. 47, Moscow, 119991, Russian Federation, eDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Türkiye, fDepartment of Physics, Faculty of Science, Eskisehir Technical University, Yunus Emre Campus 26470 Eskisehir, Türkiye, gDepartment of Physics, Faculty of Science, Erciyes University, 38039 Kayseri, Türkiye, and hDepartment of Chemistry, M.M.A.M.C (Tribhuvan University), Biratnagar, Nepal
*Correspondence e-mail: ajaya.bhattarai@mmamc.tu.edu.np
The crystal structures and Hirshfeld surface analyses of four similar E)-1-[1-(4-tert-Butylphenyl)-2,2-dichloroethenyl]-2-phenyldiazene, C18H18Cl2N2, (I), and (E)-1-[1-(4-tert-butylphenyl)-2,2-dichloroethenyl]-2-(4-methylphenyl)diazene, C19H20Cl2N2, (II), crystallize in the monoclinic C2/c with Z = 8, and (E)-1-[1-(4-tert-butylphenyl)-2,2-dichloroethenyl]-2-(4-methoxyphenyl)diazene, C19H20Cl2N2O, (III), in the monoclinic P21/c with Z = 4. (E)-1-[1-(4-tert-Butylphenyl)-2,2-dichloroethenyl]-2-(3-methylphenyl)diazene, C19H20Cl2N2, (IV), crystallizes in the triclinic P with Z = 4 and comprises two molecules (A and B) in the In the crystal structures of (I) and (II), molecules are linked by C—H⋯π and C—Cl⋯π interactions, forming layers parallel to (02), while molecules of (III) are linked by C—H⋯O contacts, C—H⋯π and C—Cl⋯π interactions forming layers parallel to (02). The stability of the molecular packing is ensured by between these layers. In the of (IV), molecules are linked by C—H⋯π and C—Cl⋯π interactions, forming a tri-periodic network.
are reported. (1. Chemical context
The synthesis of polyfunctional compounds and the study of their structures and properties are one of the directions in organic chemistry that have been studied in detail in recent years. In this regard, the synthesis of dihalogendiazabutadienes from the reaction of N-substituted 4, CBr4) in the presence of a CuCI catalyst (Maharramov et al., 2018; Shikhaliyev et al., 2019a,b, 2021a,b; Nenajdenko et al., 2020, 2022), the investigation of their structural features by the RQA method (Shikhaliyev et al., 2021c,d,e; Atioğlu et al., 2020) and the investigation of the factors affecting the direction of the reaction are distinguished by their relevance.
of benzaldehyde derivatives with polyhalomethanes (CCIThe presence of an attached diazadiene system in dihalogendiazabutadiene derivatives leads to their application as a new class of diazo dyes, and the reaction of heminal halogen atoms with various nucleophiles results in important compounds such as azidotriazoles, hydrozo derivatives of α-ketoethers and other nitrogen-containing (Shikhaliyev et al., 2021f; Tsyrenova et al., 2021).
In this context, the corresponding azo dyes were synthesized based on 4-(tert-butyl)benzaldehyde (Fig. 1), their crystal structures determined and their Hirshfeld surface analysed, and the results of these studies are reported in the current communication.
2. Structural commentary
In the I), the central fragment of the molecule, C1/C2/N1/N2/C3/C13/Cl1/Cl2, is almost planar (Fig. 2), with an r.m.s. deviation of fitted atoms of 0.0625 Å from the least-squares plane. This plane forms a dihedral angles of 26.86 (7) and 66.71 (5)° with the planes of the phenyl (C13–C18) and 4-tert-butylphenyl (C3–C8) rings, respectively. In the of (II), the central fragment (C1/C2/N2/N1/C3/C13/Cl1/Cl2; r.m.s. deviation of fitted atoms = 0.0779 Å) of the molecule (Fig. 3) makes dihedral angles of 42.41 (5) and 65.31 (4)° with the planes of the 4-methylphenyl (C13–C18) and 4-tert-butylphenyl (C3–C8) rings, respectively. In the of (III), the central fragment (C1/C2/N1/N2/C3/C13/Cl1/Cl2; r.m.s. deviation of fitted atoms = 0.0324 Å) of the molecule (Fig. 4) forms dihedral angles of 10.75 (3) and 82.00 (3)° with the planes of the 4-methoxyphenyl (C13–C18) and 4-tert-butylphenyl (C3–C8) rings, respectively.
of (In the IV), the comprises two molecules (A and B), Fig. 5. The central fragments (C1/C2/N1/N2/C3/C13/Cl1/Cl2 and C20/C21/N3/N4/C22/C32/Cl3/Cl4) of the molecules A and B are almost planar with the r.m.s. deviations of fitted atoms being 0.0336 for A and 0.0243 Å for B. The central fragment of molecule A forms dihedral angles of 13.45 (4) and 67.03 (5)°, respectively, with the planes of the 3-methylphenyl (C13–C18) and 4-tert-butylphenyl (C3–C8) rings. The central fragment of molecule B forms dihedral angles of 3.45 (2) and 84.00 (5)°, respectively, with the planes of the 3-methylphenyl (C32–C37) and 4-tert-butylphenyl (C22–C27) rings.
of (Bond lengths and angles in all compounds are in agreement with those reported for the related Database survey section.
discussed in the3. Supramolecular features and Hirshfeld surface analysis
In the crystal structures of (I) and (II), molecules are mainly connected by C—Cl⋯π interactions [for (I), C2—Cl1⋯Cg1i = 3.5617 (8) Å; 158.39 (8)°; symmetry code: (i) 1 − x, −y, 1 − z, and for (II), C2—Cl1⋯Cg1i = 3.6343 (1) Å; 160.79 (1)°, with Cg1 being the centroid of the 4-tert-butylphenyl ring (C3–C8); symmetry code: (i) 1 − x, −y, 1 − z]. These interactions, together with C—H⋯Cg1 interactions (Tables 1 and 2), lead to the formation of layers parallel to (02), Figs. 6 and 7. In the of (III), molecules are connected by C—H⋯O and C—H⋯π interactions (Table 3) and additional C—Cl⋯π [C2—Cl1⋯Cg1i = 3.7693 (1) Å; 146.35 (1) Å; Cg1 is the centroid of the 4-tert-butylphenyl ring (C3–C8); symmetry code: (i) 1 − x, −y, 1 − z], forming layers parallel to (02) (Table 3, Fig. 8). between these layers maintain the stability of the molecular packing. In the of (IV), molecules are connected via C—H⋯π (Table 4) and C—Cl⋯π [C2—Cl2⋯Cg3ii = 3.9515 (9) Å; C2—Cl2⋯Cg3ii = 165.48 (1)°; symmetry code: (ii) −x, y, −1 + z; Cg3 is the centroid of the 4-tert-butylphenyl ring (C22–C27) of molecule (IVB)] interactions, creating a tri-periodic network (Fig. 9).
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To quantify intermolecular interactions between molecules (I), (II), (III), (IVA) and (IVB) in their respective crystal structures, Hirshfeld surface analyses were performed, and the two-dimensional fingerprint plots generated with CrystalExplorer17 (Spackman et al., 2021). The two-dimensional fingerprint plots are shown in Fig. 10. Comparative interactions calculated for each compound are given in Table 5. The dominant interactions of all compounds are H⋯H [(I): 45.3%, (II): 47.1%, (III): 43.6%, (IVA): 47.0% and (IVB): 44.2%], Cl⋯H/H⋯Cl [(I): 22.8%, (II): 22.2%, (III): 21.3%, (IVA): 20.1% and (IVB): 19.8%] and C⋯H/H⋯C [(I) 17.5%, (II): 18.6%, (III): 17.0%, (IVA): 20.7% and (IVB): 21.1%]. These interactions play a crucial role in the overall stabilization of the crystal packing. The presence of different functional groups in the compounds leads to some differences in the remaining weak interactions.
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4. Database survey
A search of the Cambridge Structural Database (CSD, Version 5.42, update of September 2021; Groom et al., 2016) for the (E)-1-(2,2-dichloro-1-phenylethenyl)-2-phenyldiazene moiety resulted in 32 hits. Fourteen compounds are closely related to the title compound, viz. those with CSD refcodes TAZDIL (Atioğlu et al., 2022a), HEHKEO (Akkurt et al., 2022), ECUDAL (Atioğlu et al., 2022b), PAXDOL (Çelikesir et al., 2022), CANVUM, (Shikhaliyev et al., 2021d), EBUCUD (Shikhaliyev et al., 2021d), GUPHIL (Özkaraca et al., 2020a), DULTAI (Özkaraca et al., 2020b), XIZREG (Atioğlu et al., 2019), HODQAV (Shikhaliyev et al., 2019c), HONBUK (Akkurt et al., 2019), HONBOE (Akkurt et al., 2019), LEQXOX (Shikhaliyev et al., 2018) and LEQXIR (Shikhaliyev et al., 2018).
The molecules in TAZDIL are joined into layers parallel to (011) by C—H⋯O and C—H⋯F hydrogen bonds. C—Br⋯π and C—F⋯π contacts, as well as π–π stacking interactions strengthen the crystal packing. C—H⋯Br interactions connect the molecules in the crystal of the polymorph-1 of HEHKEO, resulting in zigzag C(8) chains along [100]. These chains are connected by C—Br⋯π interactions into layers parallel to (001). van der Waals interactions between the layers contribute to the crystal cohesion. In the crystals of ECUDAL, C—H⋯O hydrogen bonds link molecules into chains. These chains are linked by face-to-face π–π stacking interactions, resulting in a layered structure. Short intermolecular Br⋯O contacts and van der Waals interactions between the layers aid in the cohesion of the crystal packing. The molecules in the crystal of PAXDOL are connected into chains running parallel to [001] by C—H⋯O hydrogen bonds. C—F⋯π contacts and π–π stacking interactions help to consolidate the crystal packing, and short Br⋯O [2.9828 (13) Å] distances are also observed. In CANVUM, the molecules are linked by C—H⋯N interactions along [100], forming a C(6) chain. The molecules are further connected by C—Cl⋯π interactions and face-to-face π–π stacking interactions, resulting in ribbons along [100]. The of EBUCUD features short C—H⋯Cl and C—H⋯O contacts and C—H⋯π and van der Waals interactions. In GUPHIL, molecules are associated into inversion dimers via short Cl⋯Cl contacts [3.3763 (9) Å]. In DULTAI, the is stabilized by a short C—H⋯Cl contact, C—Cl⋯π and van der Waals interactions. In XIZREG, the molecules are linked by C—H⋯O hydrogen bonds into zigzag chains running along [001]. The crystal packing also features C—Cl⋯π, C—F⋯π and N—O⋯π interactions. In HODQAV, molecules are stacked in columns along [100] via weak C—H⋯Cl hydrogen bonds and face-to-face π–π stacking interactions. The crystal packing is further consolidated by short Cl⋯Cl contacts. In HONBUK and HONBOE, molecules are linked through weak X⋯Cl contacts (X = Cl for HONBUK and Br for HONBOE), C—H⋯Cl and C—Cl⋯π interactions into sheets parallel to (001). Additional van der Waals interactions consolidate the three-dimensional packing. In the crystals of LEQXOX, C—H⋯N and short Cl⋯Cl contacts are observed and in LEQXIR, C—H⋯N and C—H⋯O hydrogen bonds and short C—Cl⋯O contacts occur.
5. Synthesis and crystallization
Dyes (I), (II), (III) and (IV) were synthesized according to a literature protocol (Shikhaliyev et al., 2018).
For (I), a 20 ml screw-neck vial was charged with DMSO (10 ml), (E)-1-(4-(tert-butyl)benzylidene)-2-phenylhydrazine (252 mg, 1 mmol), tetramethylethylenediamine (TMEDA) (295 mg, 2.5 mmol), CuCl (2 mg, 0.02 mmol) and CBr4 (4.5 mmol). After 1–3 h (until TLC analysis showed complete consumption of the corresponding Schiff base), the reaction mixture was poured into a 0.01 M solution of HCl (100 ml, pH = 2–3), and extracted with dichloromethane (3× ≃ 20 ml). The combined organic phase was washed with water (3× ≃ 50 ml), brine (30 ml), dried over anhydrous Na2SO4 and concentrated in vacuo using a rotary evaporator. The residue was purified by on silica gel using appropriate mixtures of hexane and dichloromethane (v/v: 3/1–1/1). Red solid (yield 69%); m.p. 361 K. Analysis calculated for C18H18Cl2N2 (M = 333.26): 1H NMR (300 MHz, CDCl3) δ 7.87 (dd, J = 6.6, 2.9 Hz, 2H), 7.54–7.47 (m, 5H), 7.21 (d, J = 8.3 Hz, 2H), 1.44 (s, 9H). 13C NMR (75 MHz, CDCl3) δ 162.3, 153.0, 152.2, 151.6, 135.1, 131.5, 129.7, 129.3, 129.0, 125.1, 123.3, 31.4, 29.8.
For (II), the procedure was the same as that for (I) using (E)-1-(4-(tert-butyl)benzylidene)-2-(p-tolyl)hydrazine (266 mg, 1 mmol). A red solid was obtained (yield 71%); mp 369 K. Analysis calculated for C19H20Cl2N2 (M = 347.28): 1H NMR (300 MHz, CDCl3) δ 7.72 (d, J = 8.3 Hz, 2H), 7.46 (d, J = 8.3 Hz, 2H), 7.25 (d, J = 8.2 Hz, 2H), 7.15 (d, J = 8.3 Hz, 2H), 2.42 (s, 3H), 1.39 (s, 9H). 13C NMR (75 MHz, CDCl3) 152.1, 151.5, 151.1, 142.2, 134.2, 129.7, 129.7, 129.4, 125.0, 123.3, 34.8, 31.3, 21.6.
For (III), the procedure was the same as that for (I) using (E)-1-(4-(tert-butyl)benzylidene)-2-(4-methoxyphenyl)hydrazine (276 mg, 1 mmol). An orange solid was obtained (yield 63%); mp 400 K. Analysis calculated for C19H20Cl2N2O (M = 363.28): 1H NMR (300 MHz, CDCl3) δ 7.83 (d, J = 9.0 Hz, 2H), 7.48 (d, J = 8.4 Hz, 2H), 7.17 (d, J = 8.3 Hz, 2H), 6.96 (d, J = 9.0 Hz, 2H), 3.88 (s, 3H), 1.41 (s, 9H). 13C NMR (75 MHz, CDCl3) δ 162.5, 152.0, 151.4, 147.4, 132.9, 129.7, 129.6, 125.2, 125.0, 114.1, 55.5, 34.7, 31.3.
For (IV), the procedure was the same as that for (I) using (E)-1-(4-(tert-butyl)benzylidene)-2-(m-tolyl)hydrazine (276 mg, 1 mmol). An orange solid was obtained (yield 63%); mp 339 K. Analysis calculated for C19H20Cl2N2 (M = 347.28): 1 H NMR (300 MHz, CDCl3) δ 7.66 (s, 2H), 7.50 (d, J = 8.3 Hz, 2H), 7.37 (dd, J = 9.7, 6.0 Hz, 1H), 7.31 (s, 1H), 7.19 (d, J = 8.3 Hz, 2H), 2.45 (s, 3H), 1.43 (s, 9H). 13C NMR (75 MHz, CDCl3) δ δ 153.0, 152.2, 151.5, 138.9, 134.7, 132.3, 129.7, 129.3, 128.8, 125.1, 124.0, 120.3, 34.8, 31.3, 21.3.
Compounds (I), (II), (III) and (IV) were dissolved in dichloromethane and then left at room temperature for slow evaporation; red crystals of all compounds suitable for X-rays started to form after ca 2 d.
6. Refinement
Crystal data, data collection and structure . For all structures, H atoms were positioned geometrically and treated as riding atoms, with C—H = 0.95–0.98 Å and Uiso(H) = 1.2Ueq(C) or 1.5Ueq(C-methyl).
details are summarized in Table 6
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Supporting information
https://doi.org/10.1107/S205698902300511X/wm5684sup1.cif
contains datablocks I, II, III, IV, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S205698902300511X/wm5684Isup2.hkl
Structure factors: contains datablock II. DOI: https://doi.org/10.1107/S205698902300511X/wm5684IIsup3.hkl
Structure factors: contains datablock III. DOI: https://doi.org/10.1107/S205698902300511X/wm5684IIIsup4.hkl
Structure factors: contains datablock IV. DOI: https://doi.org/10.1107/S205698902300511X/wm5684IVsup5.hkl
For all structures, data collection: CrysAlis PRO (Rigaku OD, 2021); cell
CrysAlis PRO (Rigaku OD, 2021); data reduction: CrysAlis PRO (Rigaku OD, 2021); program(s) used to solve structure: SHELXT2016/6 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016/6 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2020).C18H18Cl2N2 | F(000) = 1392 |
Mr = 333.24 | Dx = 1.324 Mg m−3 |
Monoclinic, C2/c | Cu Kα radiation, λ = 1.54184 Å |
a = 31.7847 (8) Å | Cell parameters from 12999 reflections |
b = 6.0289 (1) Å | θ = 3.7–77.3° |
c = 23.7220 (6) Å | µ = 3.46 mm−1 |
β = 132.669 (4)° | T = 100 K |
V = 3342.4 (2) Å3 | Prism, red |
Z = 8 | 0.23 × 0.18 × 0.15 mm |
XtaLAB Synergy, Dualflex, HyPix diffractometer | 3242 reflections with I > 2σ(I) |
Radiation source: micro-focus sealed X-ray tube | Rint = 0.074 |
φ and ω scans | θmax = 77.7°, θmin = 3.7° |
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2021) | h = −40→33 |
Tmin = 0.339, Tmax = 0.580 | k = −7→7 |
25151 measured reflections | l = −30→30 |
3543 independent reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.038 | H-atom parameters constrained |
wR(F2) = 0.105 | w = 1/[σ2(Fo2) + (0.0617P)2 + 1.5568P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max = 0.001 |
3543 reflections | Δρmax = 0.34 e Å−3 |
202 parameters | Δρmin = −0.35 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 | 0.41113 (6) | 0.3707 (3) | 0.34806 (7) | 0.0190 (3) | |
C2 | 0.44632 (6) | 0.2439 (3) | 0.34891 (8) | 0.0202 (3) | |
C3 | 0.40396 (6) | 0.3436 (2) | 0.40351 (8) | 0.0181 (3) | |
C4 | 0.42175 (6) | 0.5130 (3) | 0.45571 (8) | 0.0209 (3) | |
H4 | 0.439678 | 0.641238 | 0.456824 | 0.025* | |
C5 | 0.41349 (6) | 0.4962 (2) | 0.50612 (8) | 0.0202 (3) | |
H5 | 0.426029 | 0.613327 | 0.541285 | 0.024* | |
C6 | 0.38719 (6) | 0.3110 (2) | 0.50615 (7) | 0.0174 (3) | |
C7 | 0.37085 (6) | 0.1406 (3) | 0.45491 (8) | 0.0202 (3) | |
H7 | 0.353829 | 0.010531 | 0.454639 | 0.024* | |
C8 | 0.37887 (6) | 0.1563 (3) | 0.40417 (8) | 0.0202 (3) | |
H8 | 0.367082 | 0.037981 | 0.369712 | 0.024* | |
C9 | 0.37725 (6) | 0.2913 (2) | 0.56103 (8) | 0.0190 (3) | |
C10 | 0.37583 (8) | 0.5188 (3) | 0.58853 (10) | 0.0298 (4) | |
H10A | 0.413067 | 0.591510 | 0.617926 | 0.045* | |
H10B | 0.367473 | 0.499800 | 0.621133 | 0.045* | |
H10C | 0.346043 | 0.610581 | 0.544116 | 0.045* | |
C11 | 0.32022 (7) | 0.1755 (3) | 0.52144 (9) | 0.0276 (3) | |
H11A | 0.289387 | 0.251751 | 0.473242 | 0.041* | |
H11B | 0.312533 | 0.179721 | 0.555056 | 0.041* | |
H11C | 0.322279 | 0.020866 | 0.510718 | 0.041* | |
C12 | 0.42652 (7) | 0.1554 (3) | 0.63116 (9) | 0.0290 (4) | |
H12A | 0.427998 | 0.009439 | 0.614365 | 0.044* | |
H12B | 0.420195 | 0.136703 | 0.665981 | 0.044* | |
H12C | 0.462777 | 0.233242 | 0.657860 | 0.044* | |
C13 | 0.31598 (6) | 0.8111 (3) | 0.23028 (8) | 0.0190 (3) | |
C14 | 0.33920 (6) | 0.9139 (3) | 0.20375 (8) | 0.0223 (3) | |
H14 | 0.373214 | 0.858034 | 0.217910 | 0.027* | |
C15 | 0.31215 (7) | 1.0977 (3) | 0.15666 (9) | 0.0263 (3) | |
H15 | 0.327976 | 1.169410 | 0.138947 | 0.032* | |
C16 | 0.26201 (7) | 1.1785 (3) | 0.13505 (8) | 0.0258 (3) | |
H16 | 0.243926 | 1.305662 | 0.103079 | 0.031* | |
C17 | 0.23826 (6) | 1.0734 (3) | 0.16015 (8) | 0.0260 (3) | |
H17 | 0.203476 | 1.126355 | 0.144314 | 0.031* | |
C18 | 0.26553 (6) | 0.8909 (3) | 0.20839 (8) | 0.0231 (3) | |
H18 | 0.249845 | 0.820563 | 0.226471 | 0.028* | |
Cl1 | 0.48464 (2) | 0.02700 (6) | 0.41131 (2) | 0.02358 (12) | |
Cl2 | 0.45673 (2) | 0.28133 (7) | 0.28705 (2) | 0.02385 (12) | |
N1 | 0.38241 (5) | 0.5414 (2) | 0.29193 (7) | 0.0193 (3) | |
N2 | 0.34302 (5) | 0.6330 (2) | 0.28416 (6) | 0.0199 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0203 (6) | 0.0199 (7) | 0.0164 (6) | −0.0021 (5) | 0.0123 (5) | −0.0010 (5) |
C2 | 0.0205 (7) | 0.0230 (7) | 0.0170 (6) | −0.0001 (5) | 0.0127 (5) | 0.0002 (5) |
C3 | 0.0195 (6) | 0.0190 (7) | 0.0164 (6) | 0.0016 (5) | 0.0123 (5) | 0.0006 (5) |
C4 | 0.0251 (7) | 0.0194 (7) | 0.0208 (6) | −0.0038 (5) | 0.0165 (6) | −0.0018 (6) |
C5 | 0.0245 (7) | 0.0186 (7) | 0.0184 (6) | −0.0035 (5) | 0.0149 (6) | −0.0044 (5) |
C6 | 0.0193 (6) | 0.0179 (7) | 0.0161 (6) | 0.0022 (5) | 0.0124 (5) | 0.0014 (5) |
C7 | 0.0245 (7) | 0.0177 (7) | 0.0214 (6) | −0.0027 (5) | 0.0168 (6) | −0.0021 (5) |
C8 | 0.0246 (7) | 0.0179 (7) | 0.0198 (6) | −0.0018 (5) | 0.0157 (6) | −0.0039 (5) |
C9 | 0.0256 (7) | 0.0175 (7) | 0.0190 (6) | 0.0018 (5) | 0.0171 (6) | 0.0012 (5) |
C10 | 0.0499 (10) | 0.0213 (8) | 0.0375 (8) | 0.0005 (7) | 0.0373 (8) | −0.0022 (7) |
C11 | 0.0296 (8) | 0.0337 (9) | 0.0284 (7) | −0.0040 (7) | 0.0232 (7) | −0.0027 (7) |
C12 | 0.0323 (8) | 0.0366 (9) | 0.0246 (7) | 0.0103 (7) | 0.0218 (7) | 0.0099 (7) |
C13 | 0.0204 (6) | 0.0203 (7) | 0.0154 (6) | −0.0014 (5) | 0.0118 (5) | −0.0025 (5) |
C14 | 0.0238 (7) | 0.0233 (7) | 0.0223 (6) | 0.0001 (6) | 0.0167 (6) | −0.0008 (6) |
C15 | 0.0295 (8) | 0.0250 (8) | 0.0261 (7) | −0.0028 (6) | 0.0196 (6) | 0.0012 (6) |
C16 | 0.0282 (8) | 0.0217 (8) | 0.0198 (6) | 0.0029 (6) | 0.0133 (6) | 0.0017 (6) |
C17 | 0.0223 (7) | 0.0308 (8) | 0.0216 (7) | 0.0048 (6) | 0.0136 (6) | −0.0002 (6) |
C18 | 0.0218 (7) | 0.0291 (8) | 0.0197 (6) | −0.0007 (6) | 0.0145 (6) | −0.0021 (6) |
Cl1 | 0.0259 (2) | 0.0243 (2) | 0.02326 (19) | 0.00553 (13) | 0.01777 (16) | 0.00450 (13) |
Cl2 | 0.0253 (2) | 0.0312 (2) | 0.02177 (19) | 0.00330 (13) | 0.01869 (16) | 0.00240 (13) |
N1 | 0.0210 (6) | 0.0201 (6) | 0.0174 (5) | −0.0001 (5) | 0.0132 (5) | −0.0006 (5) |
N2 | 0.0212 (6) | 0.0217 (6) | 0.0181 (5) | −0.0003 (5) | 0.0138 (5) | −0.0009 (5) |
C1—C2 | 1.344 (2) | C10—H10C | 0.9800 |
C1—N1 | 1.4205 (19) | C11—H11A | 0.9800 |
C1—C3 | 1.4886 (19) | C11—H11B | 0.9800 |
C2—Cl1 | 1.7146 (15) | C11—H11C | 0.9800 |
C2—Cl2 | 1.7240 (15) | C12—H12A | 0.9800 |
C3—C8 | 1.388 (2) | C12—H12B | 0.9800 |
C3—C4 | 1.396 (2) | C12—H12C | 0.9800 |
C4—C5 | 1.391 (2) | C13—C18 | 1.394 (2) |
C4—H4 | 0.9500 | C13—C14 | 1.398 (2) |
C5—C6 | 1.395 (2) | C13—N2 | 1.4269 (19) |
C5—H5 | 0.9500 | C14—C15 | 1.383 (2) |
C6—C7 | 1.396 (2) | C14—H14 | 0.9500 |
C6—C9 | 1.5381 (19) | C15—C16 | 1.390 (2) |
C7—C8 | 1.393 (2) | C15—H15 | 0.9500 |
C7—H7 | 0.9500 | C16—C17 | 1.391 (2) |
C8—H8 | 0.9500 | C16—H16 | 0.9500 |
C9—C11 | 1.532 (2) | C17—C18 | 1.388 (2) |
C9—C10 | 1.532 (2) | C17—H17 | 0.9500 |
C9—C12 | 1.536 (2) | C18—H18 | 0.9500 |
C10—H10A | 0.9800 | N1—N2 | 1.2628 (18) |
C10—H10B | 0.9800 | ||
C2—C1—N1 | 115.21 (13) | H10A—C10—H10C | 109.5 |
C2—C1—C3 | 123.29 (13) | H10B—C10—H10C | 109.5 |
N1—C1—C3 | 121.45 (13) | C9—C11—H11A | 109.5 |
C1—C2—Cl1 | 122.94 (12) | C9—C11—H11B | 109.5 |
C1—C2—Cl2 | 123.42 (12) | H11A—C11—H11B | 109.5 |
Cl1—C2—Cl2 | 113.64 (9) | C9—C11—H11C | 109.5 |
C8—C3—C4 | 118.41 (13) | H11A—C11—H11C | 109.5 |
C8—C3—C1 | 122.15 (13) | H11B—C11—H11C | 109.5 |
C4—C3—C1 | 119.42 (13) | C9—C12—H12A | 109.5 |
C5—C4—C3 | 120.69 (14) | C9—C12—H12B | 109.5 |
C5—C4—H4 | 119.7 | H12A—C12—H12B | 109.5 |
C3—C4—H4 | 119.7 | C9—C12—H12C | 109.5 |
C4—C5—C6 | 121.41 (13) | H12A—C12—H12C | 109.5 |
C4—C5—H5 | 119.3 | H12B—C12—H12C | 109.5 |
C6—C5—H5 | 119.3 | C18—C13—C14 | 120.28 (14) |
C5—C6—C7 | 117.28 (13) | C18—C13—N2 | 115.83 (13) |
C5—C6—C9 | 121.94 (13) | C14—C13—N2 | 123.75 (13) |
C7—C6—C9 | 120.78 (13) | C15—C14—C13 | 119.32 (14) |
C8—C7—C6 | 121.63 (14) | C15—C14—H14 | 120.3 |
C8—C7—H7 | 119.2 | C13—C14—H14 | 120.3 |
C6—C7—H7 | 119.2 | C14—C15—C16 | 120.54 (15) |
C3—C8—C7 | 120.55 (13) | C14—C15—H15 | 119.7 |
C3—C8—H8 | 119.7 | C16—C15—H15 | 119.7 |
C7—C8—H8 | 119.7 | C15—C16—C17 | 120.12 (15) |
C11—C9—C10 | 107.75 (13) | C15—C16—H16 | 119.9 |
C11—C9—C12 | 109.54 (13) | C17—C16—H16 | 119.9 |
C10—C9—C12 | 108.60 (13) | C18—C17—C16 | 119.81 (14) |
C11—C9—C6 | 110.65 (12) | C18—C17—H17 | 120.1 |
C10—C9—C6 | 111.93 (12) | C16—C17—H17 | 120.1 |
C12—C9—C6 | 108.33 (12) | C17—C18—C13 | 119.91 (14) |
C9—C10—H10A | 109.5 | C17—C18—H18 | 120.0 |
C9—C10—H10B | 109.5 | C13—C18—H18 | 120.0 |
H10A—C10—H10B | 109.5 | N2—N1—C1 | 113.43 (12) |
C9—C10—H10C | 109.5 | N1—N2—C13 | 113.31 (12) |
N1—C1—C2—Cl1 | −179.36 (10) | C7—C6—C9—C11 | −37.58 (18) |
C3—C1—C2—Cl1 | 3.2 (2) | C5—C6—C9—C10 | 23.30 (19) |
N1—C1—C2—Cl2 | −0.05 (19) | C7—C6—C9—C10 | −157.77 (14) |
C3—C1—C2—Cl2 | −177.52 (11) | C5—C6—C9—C12 | −96.41 (16) |
C2—C1—C3—C8 | −67.0 (2) | C7—C6—C9—C12 | 82.52 (17) |
N1—C1—C3—C8 | 115.67 (16) | C18—C13—C14—C15 | 1.1 (2) |
C2—C1—C3—C4 | 114.42 (17) | N2—C13—C14—C15 | −174.40 (14) |
N1—C1—C3—C4 | −62.90 (18) | C13—C14—C15—C16 | −0.8 (2) |
C8—C3—C4—C5 | −1.2 (2) | C14—C15—C16—C17 | −0.6 (2) |
C1—C3—C4—C5 | 177.40 (13) | C15—C16—C17—C18 | 1.6 (2) |
C3—C4—C5—C6 | −0.2 (2) | C16—C17—C18—C13 | −1.3 (2) |
C4—C5—C6—C7 | 1.7 (2) | C14—C13—C18—C17 | −0.1 (2) |
C4—C5—C6—C9 | −179.38 (13) | N2—C13—C18—C17 | 175.75 (13) |
C5—C6—C7—C8 | −1.8 (2) | C2—C1—N1—N2 | 169.00 (13) |
C9—C6—C7—C8 | 179.25 (13) | C3—C1—N1—N2 | −13.47 (19) |
C4—C3—C8—C7 | 1.1 (2) | C1—N1—N2—C13 | 177.31 (11) |
C1—C3—C8—C7 | −177.48 (13) | C18—C13—N2—N1 | 168.30 (13) |
C6—C7—C8—C3 | 0.4 (2) | C14—C13—N2—N1 | −16.0 (2) |
C5—C6—C9—C11 | 143.50 (14) |
Cg1 is the centroid of the 4-tert-butylphenyl ring (C3–C8). |
D—H···A | D—H | H···A | D···A | D—H···A |
C17—H17···Cg1i | 0.95 | 2.95 | 3.476 (2) | 116 |
Symmetry code: (i) −x+1/2, y+1/2, −z+1/2. |
C19H20Cl2N2 | F(000) = 1456 |
Mr = 347.27 | Dx = 1.280 Mg m−3 |
Monoclinic, C2/c | Cu Kα radiation, λ = 1.54184 Å |
a = 30.9062 (6) Å | Cell parameters from 19033 reflections |
b = 6.27248 (5) Å | θ = 3.6–77.1° |
c = 23.3475 (4) Å | µ = 3.23 mm−1 |
β = 127.223 (3)° | T = 100 K |
V = 3604.08 (15) Å3 | Prism, red |
Z = 8 | 0.19 × 0.17 × 0.14 mm |
XtaLAB Synergy, Dualflex, HyPix diffractometer | 3643 reflections with I > 2σ(I) |
Radiation source: micro-focus sealed X-ray tube | Rint = 0.047 |
φ and ω scans | θmax = 77.5°, θmin = 3.6° |
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2021) | h = −38→38 |
Tmin = 0.464, Tmax = 0.630 | k = −6→7 |
28692 measured reflections | l = −29→29 |
3805 independent reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.033 | w = 1/[σ2(Fo2) + (0.047P)2 + 2.8P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.090 | (Δ/σ)max = 0.001 |
S = 1.10 | Δρmax = 0.29 e Å−3 |
3805 reflections | Δρmin = −0.30 e Å−3 |
213 parameters | Extinction correction: SHELXL2016/6 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.00017 (5) |
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 | ||
Cl1 | 0.48998 (2) | 0.03552 (5) | 0.41749 (2) | 0.02454 (11) | |
Cl2 | 0.46363 (2) | 0.25942 (5) | 0.29246 (2) | 0.02446 (11) | |
N1 | 0.39101 (4) | 0.51844 (18) | 0.30369 (6) | 0.0208 (2) | |
N2 | 0.35039 (5) | 0.59579 (18) | 0.29674 (6) | 0.0222 (2) | |
C1 | 0.41805 (5) | 0.3591 (2) | 0.35785 (7) | 0.0201 (3) | |
C2 | 0.45276 (5) | 0.2354 (2) | 0.35637 (7) | 0.0208 (3) | |
C3 | 0.40920 (5) | 0.3421 (2) | 0.41360 (7) | 0.0195 (3) | |
C4 | 0.42254 (6) | 0.5155 (2) | 0.45907 (7) | 0.0227 (3) | |
H4 | 0.438159 | 0.639440 | 0.455003 | 0.027* | |
C5 | 0.41316 (6) | 0.5082 (2) | 0.51023 (7) | 0.0220 (3) | |
H5 | 0.422523 | 0.627803 | 0.540667 | 0.026* | |
C6 | 0.39028 (5) | 0.3292 (2) | 0.51781 (7) | 0.0191 (3) | |
C7 | 0.37776 (5) | 0.1560 (2) | 0.47236 (7) | 0.0211 (3) | |
H7 | 0.362819 | 0.030753 | 0.477002 | 0.025* | |
C8 | 0.38657 (5) | 0.1621 (2) | 0.42057 (7) | 0.0209 (3) | |
H8 | 0.377088 | 0.042930 | 0.389929 | 0.025* | |
C9 | 0.38015 (5) | 0.3145 (2) | 0.57443 (7) | 0.0206 (3) | |
C10 | 0.38607 (6) | 0.5300 (2) | 0.60923 (8) | 0.0284 (3) | |
H10A | 0.423263 | 0.582766 | 0.634072 | 0.043* | |
H10B | 0.378300 | 0.513209 | 0.643923 | 0.043* | |
H10C | 0.360454 | 0.632136 | 0.571982 | 0.043* | |
C11 | 0.32232 (6) | 0.2333 (3) | 0.53954 (8) | 0.0295 (3) | |
H11A | 0.296101 | 0.325794 | 0.499032 | 0.044* | |
H11B | 0.315190 | 0.234963 | 0.575128 | 0.044* | |
H11C | 0.318734 | 0.087345 | 0.522185 | 0.044* | |
C12 | 0.42191 (6) | 0.1599 (3) | 0.63358 (8) | 0.0315 (3) | |
H12A | 0.417802 | 0.019311 | 0.612496 | 0.047* | |
H12B | 0.415934 | 0.147896 | 0.670170 | 0.047* | |
H12C | 0.458667 | 0.213787 | 0.655851 | 0.047* | |
C13 | 0.32527 (5) | 0.7652 (2) | 0.24618 (7) | 0.0199 (3) | |
C14 | 0.35328 (5) | 0.8930 (2) | 0.22966 (7) | 0.0221 (3) | |
H14 | 0.390374 | 0.865296 | 0.250923 | 0.027* | |
C15 | 0.32646 (6) | 1.0606 (2) | 0.18195 (8) | 0.0252 (3) | |
H15 | 0.345643 | 1.148864 | 0.171144 | 0.030* | |
C16 | 0.27186 (6) | 1.1026 (2) | 0.14946 (7) | 0.0247 (3) | |
C17 | 0.24436 (6) | 0.9736 (2) | 0.16630 (8) | 0.0263 (3) | |
H17 | 0.206996 | 0.999041 | 0.144008 | 0.032* | |
C18 | 0.27109 (6) | 0.8078 (2) | 0.21550 (8) | 0.0261 (3) | |
H18 | 0.252413 | 0.723936 | 0.228125 | 0.031* | |
C19 | 0.24335 (7) | 1.2860 (3) | 0.09755 (9) | 0.0361 (4) | |
H19A | 0.204956 | 1.250175 | 0.061231 | 0.054* | |
H19B | 0.260343 | 1.313112 | 0.073900 | 0.054* | |
H19C | 0.246248 | 1.413799 | 0.123816 | 0.054* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.02633 (18) | 0.02606 (18) | 0.02459 (17) | 0.00732 (11) | 0.01716 (14) | 0.00613 (11) |
Cl2 | 0.02460 (18) | 0.03214 (19) | 0.02356 (17) | 0.00413 (12) | 0.01819 (15) | 0.00397 (11) |
N1 | 0.0216 (5) | 0.0219 (5) | 0.0208 (5) | 0.0017 (4) | 0.0139 (4) | 0.0011 (4) |
N2 | 0.0225 (5) | 0.0241 (5) | 0.0229 (5) | 0.0014 (4) | 0.0153 (5) | 0.0021 (4) |
C1 | 0.0210 (6) | 0.0207 (6) | 0.0197 (6) | −0.0009 (5) | 0.0129 (5) | 0.0008 (5) |
C2 | 0.0207 (6) | 0.0241 (6) | 0.0192 (6) | 0.0006 (5) | 0.0129 (5) | 0.0022 (5) |
C3 | 0.0192 (6) | 0.0211 (6) | 0.0194 (6) | 0.0021 (5) | 0.0123 (5) | 0.0018 (5) |
C4 | 0.0268 (7) | 0.0202 (6) | 0.0242 (6) | −0.0034 (5) | 0.0170 (6) | −0.0009 (5) |
C5 | 0.0256 (6) | 0.0201 (6) | 0.0229 (6) | −0.0030 (5) | 0.0160 (5) | −0.0029 (5) |
C6 | 0.0178 (6) | 0.0210 (6) | 0.0191 (6) | 0.0023 (5) | 0.0115 (5) | 0.0014 (5) |
C7 | 0.0246 (6) | 0.0184 (6) | 0.0253 (6) | −0.0019 (5) | 0.0177 (5) | −0.0005 (5) |
C8 | 0.0236 (6) | 0.0190 (6) | 0.0227 (6) | −0.0001 (5) | 0.0153 (5) | −0.0016 (5) |
C9 | 0.0223 (6) | 0.0225 (6) | 0.0213 (6) | −0.0007 (5) | 0.0154 (5) | −0.0007 (5) |
C10 | 0.0361 (8) | 0.0275 (7) | 0.0312 (7) | −0.0034 (6) | 0.0255 (7) | −0.0064 (6) |
C11 | 0.0278 (7) | 0.0386 (8) | 0.0303 (7) | −0.0081 (6) | 0.0218 (6) | −0.0078 (6) |
C12 | 0.0361 (8) | 0.0381 (8) | 0.0308 (7) | 0.0110 (6) | 0.0258 (7) | 0.0103 (6) |
C13 | 0.0225 (6) | 0.0208 (6) | 0.0188 (6) | 0.0018 (5) | 0.0138 (5) | 0.0002 (5) |
C14 | 0.0208 (6) | 0.0237 (6) | 0.0245 (6) | 0.0015 (5) | 0.0151 (5) | 0.0008 (5) |
C15 | 0.0266 (7) | 0.0237 (6) | 0.0287 (7) | 0.0010 (5) | 0.0185 (6) | 0.0036 (5) |
C16 | 0.0274 (7) | 0.0218 (6) | 0.0230 (6) | 0.0036 (5) | 0.0143 (6) | 0.0002 (5) |
C17 | 0.0217 (6) | 0.0290 (7) | 0.0284 (7) | 0.0048 (5) | 0.0151 (6) | 0.0016 (5) |
C18 | 0.0243 (7) | 0.0299 (7) | 0.0293 (7) | 0.0016 (5) | 0.0189 (6) | 0.0026 (6) |
C19 | 0.0327 (8) | 0.0305 (8) | 0.0383 (8) | 0.0102 (6) | 0.0180 (7) | 0.0111 (6) |
Cl1—C2 | 1.7163 (13) | C10—H10B | 0.9800 |
Cl2—C2 | 1.7229 (13) | C10—H10C | 0.9800 |
N1—N2 | 1.2613 (16) | C11—H11A | 0.9800 |
N1—C1 | 1.4202 (16) | C11—H11B | 0.9800 |
N2—C13 | 1.4199 (17) | C11—H11C | 0.9800 |
C1—C2 | 1.3415 (19) | C12—H12A | 0.9800 |
C1—C3 | 1.4871 (17) | C12—H12B | 0.9800 |
C3—C8 | 1.3887 (18) | C12—H12C | 0.9800 |
C3—C4 | 1.3964 (18) | C13—C18 | 1.3921 (19) |
C4—C5 | 1.3898 (19) | C13—C14 | 1.3944 (18) |
C4—H4 | 0.9500 | C14—C15 | 1.3844 (19) |
C5—C6 | 1.3942 (18) | C14—H14 | 0.9500 |
C5—H5 | 0.9500 | C15—C16 | 1.394 (2) |
C6—C7 | 1.3995 (18) | C15—H15 | 0.9500 |
C6—C9 | 1.5348 (17) | C16—C17 | 1.391 (2) |
C7—C8 | 1.3915 (18) | C16—C19 | 1.5089 (19) |
C7—H7 | 0.9500 | C17—C18 | 1.391 (2) |
C8—H8 | 0.9500 | C17—H17 | 0.9500 |
C9—C10 | 1.5303 (18) | C18—H18 | 0.9500 |
C9—C11 | 1.5349 (18) | C19—H19A | 0.9800 |
C9—C12 | 1.5353 (19) | C19—H19B | 0.9800 |
C10—H10A | 0.9800 | C19—H19C | 0.9800 |
N2—N1—C1 | 112.90 (11) | H10B—C10—H10C | 109.5 |
N1—N2—C13 | 113.32 (10) | C9—C11—H11A | 109.5 |
C2—C1—N1 | 115.67 (11) | C9—C11—H11B | 109.5 |
C2—C1—C3 | 123.67 (12) | H11A—C11—H11B | 109.5 |
N1—C1—C3 | 120.60 (11) | C9—C11—H11C | 109.5 |
C1—C2—Cl1 | 123.05 (10) | H11A—C11—H11C | 109.5 |
C1—C2—Cl2 | 123.35 (10) | H11B—C11—H11C | 109.5 |
Cl1—C2—Cl2 | 113.60 (7) | C9—C12—H12A | 109.5 |
C8—C3—C4 | 118.82 (12) | C9—C12—H12B | 109.5 |
C8—C3—C1 | 122.23 (12) | H12A—C12—H12B | 109.5 |
C4—C3—C1 | 118.92 (11) | C9—C12—H12C | 109.5 |
C5—C4—C3 | 120.59 (12) | H12A—C12—H12C | 109.5 |
C5—C4—H4 | 119.7 | H12B—C12—H12C | 109.5 |
C3—C4—H4 | 119.7 | C18—C13—C14 | 120.14 (12) |
C4—C5—C6 | 121.38 (12) | C18—C13—N2 | 117.00 (12) |
C4—C5—H5 | 119.3 | C14—C13—N2 | 122.78 (12) |
C6—C5—H5 | 119.3 | C15—C14—C13 | 119.31 (12) |
C5—C6—C7 | 117.26 (11) | C15—C14—H14 | 120.3 |
C5—C6—C9 | 122.75 (11) | C13—C14—H14 | 120.3 |
C7—C6—C9 | 119.96 (11) | C14—C15—C16 | 121.31 (13) |
C8—C7—C6 | 121.85 (12) | C14—C15—H15 | 119.3 |
C8—C7—H7 | 119.1 | C16—C15—H15 | 119.3 |
C6—C7—H7 | 119.1 | C17—C16—C15 | 118.81 (12) |
C3—C8—C7 | 120.09 (12) | C17—C16—C19 | 120.69 (13) |
C3—C8—H8 | 120.0 | C15—C16—C19 | 120.49 (13) |
C7—C8—H8 | 120.0 | C18—C17—C16 | 120.58 (13) |
C10—C9—C6 | 112.52 (11) | C18—C17—H17 | 119.7 |
C10—C9—C11 | 107.56 (11) | C16—C17—H17 | 119.7 |
C6—C9—C11 | 109.98 (10) | C17—C18—C13 | 119.81 (13) |
C10—C9—C12 | 108.35 (12) | C17—C18—H18 | 120.1 |
C6—C9—C12 | 108.31 (10) | C13—C18—H18 | 120.1 |
C11—C9—C12 | 110.09 (12) | C16—C19—H19A | 109.5 |
C9—C10—H10A | 109.5 | C16—C19—H19B | 109.5 |
C9—C10—H10B | 109.5 | H19A—C19—H19B | 109.5 |
H10A—C10—H10B | 109.5 | C16—C19—H19C | 109.5 |
C9—C10—H10C | 109.5 | H19A—C19—H19C | 109.5 |
H10A—C10—H10C | 109.5 | H19B—C19—H19C | 109.5 |
C1—N1—N2—C13 | 175.97 (11) | C6—C7—C8—C3 | 1.1 (2) |
N2—N1—C1—C2 | 164.44 (12) | C5—C6—C9—C10 | 12.41 (17) |
N2—N1—C1—C3 | −18.16 (17) | C7—C6—C9—C10 | −169.31 (12) |
N1—C1—C2—Cl1 | 179.34 (9) | C5—C6—C9—C11 | 132.31 (13) |
C3—C1—C2—Cl1 | 2.03 (19) | C7—C6—C9—C11 | −49.41 (16) |
N1—C1—C2—Cl2 | −1.51 (18) | C5—C6—C9—C12 | −107.35 (14) |
C3—C1—C2—Cl2 | −178.82 (10) | C7—C6—C9—C12 | 70.94 (15) |
C2—C1—C3—C8 | −65.16 (18) | N1—N2—C13—C18 | 157.20 (12) |
N1—C1—C3—C8 | 117.65 (14) | N1—N2—C13—C14 | −26.07 (18) |
C2—C1—C3—C4 | 116.87 (15) | C18—C13—C14—C15 | −0.7 (2) |
N1—C1—C3—C4 | −60.31 (17) | N2—C13—C14—C15 | −177.35 (12) |
C8—C3—C4—C5 | −0.2 (2) | C13—C14—C15—C16 | −0.8 (2) |
C1—C3—C4—C5 | 177.83 (12) | C14—C15—C16—C17 | 0.7 (2) |
C3—C4—C5—C6 | 0.0 (2) | C14—C15—C16—C19 | −179.95 (14) |
C4—C5—C6—C7 | 0.74 (19) | C15—C16—C17—C18 | 0.9 (2) |
C4—C5—C6—C9 | 179.07 (12) | C19—C16—C17—C18 | −178.43 (14) |
C5—C6—C7—C8 | −1.27 (19) | C16—C17—C18—C13 | −2.4 (2) |
C9—C6—C7—C8 | −179.65 (12) | C14—C13—C18—C17 | 2.3 (2) |
C4—C3—C8—C7 | −0.30 (19) | N2—C13—C18—C17 | 179.13 (12) |
C1—C3—C8—C7 | −178.27 (12) |
Cg1 is the centroid of the 4-tert-butylphenyl ring (C3–C8). |
D—H···A | D—H | H···A | D···A | D—H···A |
C17—H17···Cg1i | 0.95 | 2.88 | 3.675 (2) | 142 |
Symmetry code: (i) −x+1/2, y+1/2, −z+1/2. |
C19H20Cl2N2O | F(000) = 760 |
Mr = 363.27 | Dx = 1.323 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54184 Å |
a = 13.8738 (2) Å | Cell parameters from 17727 reflections |
b = 12.5946 (2) Å | θ = 3.4–77.6° |
c = 11.3013 (1) Å | µ = 3.26 mm−1 |
β = 112.505 (1)° | T = 100 K |
V = 1824.35 (4) Å3 | Prism, red |
Z = 4 | 0.24 × 0.20 × 0.18 mm |
XtaLAB Synergy, Dualflex, HyPix diffractometer | 3603 reflections with I > 2σ(I) |
Radiation source: micro-focus sealed X-ray tube | Rint = 0.076 |
φ and ω scans | θmax = 77.9°, θmin = 3.5° |
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2021) | h = −15→17 |
Tmin = 0.431, Tmax = 0.550 | k = −15→15 |
25894 measured reflections | l = −14→14 |
3843 independent reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.043 | H-atom parameters constrained |
wR(F2) = 0.118 | w = 1/[σ2(Fo2) + (0.0831P)2 + 0.4008P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
3843 reflections | Δρmax = 0.53 e Å−3 |
221 parameters | Δρmin = −0.33 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 | 0.20324 (11) | 0.34882 (11) | 0.22693 (13) | 0.0187 (3) | |
C2 | 0.14902 (11) | 0.30352 (11) | 0.11245 (13) | 0.0202 (3) | |
C3 | 0.19934 (10) | 0.46520 (11) | 0.24859 (12) | 0.0176 (3) | |
C4 | 0.13412 (10) | 0.50501 (11) | 0.30620 (13) | 0.0189 (3) | |
H4 | 0.093607 | 0.457391 | 0.333412 | 0.023* | |
C5 | 0.12770 (10) | 0.61349 (11) | 0.32425 (13) | 0.0188 (3) | |
H5 | 0.081387 | 0.638876 | 0.361713 | 0.023* | |
C6 | 0.18772 (10) | 0.68598 (11) | 0.28860 (12) | 0.0170 (3) | |
C7 | 0.25514 (11) | 0.64453 (12) | 0.23454 (14) | 0.0213 (3) | |
H7 | 0.298483 | 0.691647 | 0.211415 | 0.026* | |
C8 | 0.26040 (11) | 0.53661 (12) | 0.21381 (13) | 0.0214 (3) | |
H8 | 0.306116 | 0.511166 | 0.175511 | 0.026* | |
C9 | 0.18118 (11) | 0.80655 (11) | 0.30498 (13) | 0.0205 (3) | |
C10 | 0.09974 (13) | 0.83569 (12) | 0.35970 (16) | 0.0268 (3) | |
H10A | 0.030833 | 0.811599 | 0.301035 | 0.040* | |
H10B | 0.098759 | 0.912885 | 0.370051 | 0.040* | |
H10C | 0.117338 | 0.801296 | 0.443148 | 0.040* | |
C11 | 0.28773 (13) | 0.84892 (13) | 0.39614 (16) | 0.0282 (3) | |
H11A | 0.305696 | 0.817148 | 0.481074 | 0.042* | |
H11B | 0.284263 | 0.926299 | 0.402705 | 0.042* | |
H11C | 0.341121 | 0.830301 | 0.362727 | 0.042* | |
C12 | 0.15139 (14) | 0.86056 (13) | 0.17359 (15) | 0.0298 (3) | |
H12A | 0.205161 | 0.845923 | 0.139406 | 0.045* | |
H12B | 0.145827 | 0.937393 | 0.183169 | 0.045* | |
H12C | 0.084214 | 0.832769 | 0.114538 | 0.045* | |
C13 | 0.37438 (10) | 0.24915 (11) | 0.52562 (13) | 0.0184 (3) | |
C14 | 0.39042 (11) | 0.14261 (11) | 0.50182 (13) | 0.0193 (3) | |
H14 | 0.360543 | 0.115106 | 0.417218 | 0.023* | |
C15 | 0.44961 (11) | 0.07799 (11) | 0.60150 (13) | 0.0198 (3) | |
H15 | 0.461097 | 0.006053 | 0.585247 | 0.024* | |
C16 | 0.49311 (10) | 0.11785 (11) | 0.72709 (13) | 0.0186 (3) | |
C17 | 0.47838 (11) | 0.22386 (11) | 0.75109 (13) | 0.0199 (3) | |
H17 | 0.508107 | 0.251380 | 0.835695 | 0.024* | |
C18 | 0.41964 (11) | 0.28891 (11) | 0.64970 (13) | 0.0206 (3) | |
H18 | 0.410262 | 0.361533 | 0.665345 | 0.025* | |
C19 | 0.59249 (13) | 0.08155 (13) | 0.94780 (14) | 0.0275 (3) | |
H19A | 0.641917 | 0.139312 | 0.955751 | 0.041* | |
H19B | 0.629032 | 0.022336 | 1.003028 | 0.041* | |
H19C | 0.536817 | 0.107057 | 0.973833 | 0.041* | |
Cl1 | 0.07489 (3) | 0.37510 (3) | −0.01999 (3) | 0.02558 (13) | |
Cl2 | 0.14590 (3) | 0.16875 (3) | 0.08679 (3) | 0.02464 (13) | |
N1 | 0.26151 (9) | 0.27761 (9) | 0.32441 (11) | 0.0193 (2) | |
N2 | 0.31434 (9) | 0.32201 (9) | 0.42989 (11) | 0.0195 (2) | |
O1 | 0.54829 (8) | 0.04642 (8) | 0.81760 (10) | 0.0246 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0212 (6) | 0.0180 (6) | 0.0175 (6) | 0.0014 (5) | 0.0081 (5) | 0.0008 (5) |
C2 | 0.0227 (7) | 0.0178 (6) | 0.0191 (6) | −0.0003 (5) | 0.0070 (5) | 0.0001 (5) |
C3 | 0.0202 (6) | 0.0168 (6) | 0.0139 (6) | 0.0012 (5) | 0.0042 (5) | 0.0002 (5) |
C4 | 0.0200 (6) | 0.0193 (7) | 0.0168 (6) | −0.0019 (5) | 0.0064 (5) | 0.0009 (5) |
C5 | 0.0192 (6) | 0.0207 (7) | 0.0168 (6) | 0.0004 (5) | 0.0072 (5) | −0.0002 (5) |
C6 | 0.0188 (6) | 0.0167 (6) | 0.0129 (6) | 0.0002 (5) | 0.0034 (5) | 0.0002 (5) |
C7 | 0.0237 (7) | 0.0200 (7) | 0.0227 (7) | −0.0028 (5) | 0.0116 (6) | 0.0008 (5) |
C8 | 0.0240 (7) | 0.0217 (7) | 0.0219 (6) | 0.0017 (5) | 0.0126 (5) | 0.0008 (5) |
C9 | 0.0253 (7) | 0.0156 (6) | 0.0193 (6) | −0.0009 (5) | 0.0071 (5) | −0.0007 (5) |
C10 | 0.0318 (8) | 0.0185 (7) | 0.0316 (8) | 0.0042 (6) | 0.0137 (6) | −0.0015 (6) |
C11 | 0.0293 (8) | 0.0225 (7) | 0.0301 (8) | −0.0055 (6) | 0.0084 (6) | −0.0064 (6) |
C12 | 0.0457 (9) | 0.0192 (7) | 0.0230 (7) | 0.0005 (6) | 0.0114 (7) | 0.0031 (6) |
C13 | 0.0204 (6) | 0.0172 (6) | 0.0171 (6) | −0.0002 (5) | 0.0065 (5) | 0.0010 (5) |
C14 | 0.0219 (7) | 0.0182 (6) | 0.0179 (6) | −0.0018 (5) | 0.0079 (5) | −0.0020 (5) |
C15 | 0.0227 (6) | 0.0157 (6) | 0.0202 (6) | −0.0001 (5) | 0.0073 (5) | −0.0005 (5) |
C16 | 0.0181 (6) | 0.0180 (7) | 0.0185 (6) | 0.0003 (5) | 0.0056 (5) | 0.0030 (5) |
C17 | 0.0218 (6) | 0.0193 (7) | 0.0169 (6) | −0.0010 (5) | 0.0054 (5) | −0.0012 (5) |
C18 | 0.0242 (7) | 0.0165 (6) | 0.0198 (6) | −0.0001 (5) | 0.0069 (5) | −0.0009 (5) |
C19 | 0.0326 (8) | 0.0238 (7) | 0.0183 (7) | 0.0041 (6) | 0.0009 (6) | 0.0018 (5) |
Cl1 | 0.0307 (2) | 0.0239 (2) | 0.01655 (19) | 0.00034 (12) | 0.00291 (15) | 0.00222 (11) |
Cl2 | 0.0306 (2) | 0.0173 (2) | 0.0225 (2) | −0.00119 (12) | 0.00626 (15) | −0.00440 (11) |
N1 | 0.0219 (6) | 0.0179 (6) | 0.0168 (5) | 0.0010 (4) | 0.0059 (4) | 0.0004 (4) |
N2 | 0.0225 (6) | 0.0178 (6) | 0.0170 (5) | 0.0010 (4) | 0.0064 (5) | 0.0004 (4) |
O1 | 0.0301 (5) | 0.0187 (5) | 0.0190 (5) | 0.0039 (4) | 0.0027 (4) | 0.0019 (4) |
C1—C2 | 1.349 (2) | C11—H11B | 0.9800 |
C1—N1 | 1.4106 (18) | C11—H11C | 0.9800 |
C1—C3 | 1.4904 (19) | C12—H12A | 0.9800 |
C2—Cl1 | 1.7125 (14) | C12—H12B | 0.9800 |
C2—Cl2 | 1.7196 (15) | C12—H12C | 0.9800 |
C3—C8 | 1.3913 (19) | C13—C18 | 1.3920 (19) |
C3—C4 | 1.3947 (19) | C13—C14 | 1.4029 (19) |
C4—C5 | 1.389 (2) | C13—N2 | 1.4200 (18) |
C4—H4 | 0.9500 | C14—C15 | 1.377 (2) |
C5—C6 | 1.3951 (19) | C14—H14 | 0.9500 |
C5—H5 | 0.9500 | C15—C16 | 1.405 (2) |
C6—C7 | 1.3993 (19) | C15—H15 | 0.9500 |
C6—C9 | 1.5366 (19) | C16—O1 | 1.3573 (17) |
C7—C8 | 1.386 (2) | C16—C17 | 1.393 (2) |
C7—H7 | 0.9500 | C17—C18 | 1.3905 (19) |
C8—H8 | 0.9500 | C17—H17 | 0.9500 |
C9—C10 | 1.526 (2) | C18—H18 | 0.9500 |
C9—C11 | 1.538 (2) | C19—O1 | 1.4305 (18) |
C9—C12 | 1.539 (2) | C19—H19A | 0.9800 |
C10—H10A | 0.9800 | C19—H19B | 0.9800 |
C10—H10B | 0.9800 | C19—H19C | 0.9800 |
C10—H10C | 0.9800 | N1—N2 | 1.2658 (17) |
C11—H11A | 0.9800 | ||
C2—C1—N1 | 114.99 (12) | H11A—C11—H11B | 109.5 |
C2—C1—C3 | 122.10 (13) | C9—C11—H11C | 109.5 |
N1—C1—C3 | 122.89 (12) | H11A—C11—H11C | 109.5 |
C1—C2—Cl1 | 122.91 (11) | H11B—C11—H11C | 109.5 |
C1—C2—Cl2 | 123.23 (11) | C9—C12—H12A | 109.5 |
Cl1—C2—Cl2 | 113.85 (8) | C9—C12—H12B | 109.5 |
C8—C3—C4 | 118.26 (13) | H12A—C12—H12B | 109.5 |
C8—C3—C1 | 121.67 (12) | C9—C12—H12C | 109.5 |
C4—C3—C1 | 120.07 (12) | H12A—C12—H12C | 109.5 |
C5—C4—C3 | 120.77 (12) | H12B—C12—H12C | 109.5 |
C5—C4—H4 | 119.6 | C18—C13—C14 | 119.59 (13) |
C3—C4—H4 | 119.6 | C18—C13—N2 | 116.23 (12) |
C4—C5—C6 | 121.48 (12) | C14—C13—N2 | 124.19 (12) |
C4—C5—H5 | 119.3 | C15—C14—C13 | 119.80 (13) |
C6—C5—H5 | 119.3 | C15—C14—H14 | 120.1 |
C5—C6—C7 | 117.03 (13) | C13—C14—H14 | 120.1 |
C5—C6—C9 | 122.86 (12) | C14—C15—C16 | 120.40 (13) |
C7—C6—C9 | 120.10 (12) | C14—C15—H15 | 119.8 |
C8—C7—C6 | 121.80 (13) | C16—C15—H15 | 119.8 |
C8—C7—H7 | 119.1 | O1—C16—C17 | 124.82 (13) |
C6—C7—H7 | 119.1 | O1—C16—C15 | 115.13 (12) |
C7—C8—C3 | 120.60 (13) | C17—C16—C15 | 120.05 (12) |
C7—C8—H8 | 119.7 | C18—C17—C16 | 119.19 (12) |
C3—C8—H8 | 119.7 | C18—C17—H17 | 120.4 |
C10—C9—C6 | 111.93 (12) | C16—C17—H17 | 120.4 |
C10—C9—C11 | 108.42 (12) | C17—C18—C13 | 120.95 (13) |
C6—C9—C11 | 109.73 (12) | C17—C18—H18 | 119.5 |
C10—C9—C12 | 108.52 (13) | C13—C18—H18 | 119.5 |
C6—C9—C12 | 109.09 (11) | O1—C19—H19A | 109.5 |
C11—C9—C12 | 109.10 (13) | O1—C19—H19B | 109.5 |
C9—C10—H10A | 109.5 | H19A—C19—H19B | 109.5 |
C9—C10—H10B | 109.5 | O1—C19—H19C | 109.5 |
H10A—C10—H10B | 109.5 | H19A—C19—H19C | 109.5 |
C9—C10—H10C | 109.5 | H19B—C19—H19C | 109.5 |
H10A—C10—H10C | 109.5 | N2—N1—C1 | 114.00 (12) |
H10B—C10—H10C | 109.5 | N1—N2—C13 | 113.04 (11) |
C9—C11—H11A | 109.5 | C16—O1—C19 | 117.79 (11) |
C9—C11—H11B | 109.5 | ||
N1—C1—C2—Cl1 | −178.80 (10) | C7—C6—C9—C11 | −62.26 (17) |
C3—C1—C2—Cl1 | 2.57 (19) | C5—C6—C9—C12 | −122.02 (15) |
N1—C1—C2—Cl2 | 2.48 (18) | C7—C6—C9—C12 | 57.21 (17) |
C3—C1—C2—Cl2 | −176.14 (10) | C18—C13—C14—C15 | 0.8 (2) |
C2—C1—C3—C8 | −82.01 (18) | N2—C13—C14—C15 | −179.66 (12) |
N1—C1—C3—C8 | 99.47 (16) | C13—C14—C15—C16 | 0.7 (2) |
C2—C1—C3—C4 | 98.64 (16) | C14—C15—C16—O1 | 178.87 (12) |
N1—C1—C3—C4 | −79.88 (17) | C14—C15—C16—C17 | −1.4 (2) |
C8—C3—C4—C5 | 2.2 (2) | O1—C16—C17—C18 | −179.72 (13) |
C1—C3—C4—C5 | −178.43 (12) | C15—C16—C17—C18 | 0.5 (2) |
C3—C4—C5—C6 | −1.6 (2) | C16—C17—C18—C13 | 1.0 (2) |
C4—C5—C6—C7 | −0.37 (19) | C14—C13—C18—C17 | −1.7 (2) |
C4—C5—C6—C9 | 178.89 (12) | N2—C13—C18—C17 | 178.79 (12) |
C5—C6—C7—C8 | 1.7 (2) | C2—C1—N1—N2 | 177.92 (12) |
C9—C6—C7—C8 | −177.56 (13) | C3—C1—N1—N2 | −3.46 (18) |
C6—C7—C8—C3 | −1.1 (2) | C1—N1—N2—C13 | −178.51 (11) |
C4—C3—C8—C7 | −0.9 (2) | C18—C13—N2—N1 | −168.92 (12) |
C1—C3—C8—C7 | 179.78 (13) | C14—C13—N2—N1 | 11.54 (18) |
C5—C6—C9—C10 | −1.92 (18) | C17—C16—O1—C19 | 1.7 (2) |
C7—C6—C9—C10 | 177.32 (13) | C15—C16—O1—C19 | −178.58 (13) |
C5—C6—C9—C11 | 118.51 (14) |
Cg1 is the centroid of the 4-tert-butylphenyl ring (C3–C8). |
D—H···A | D—H | H···A | D···A | D—H···A |
C18—H18···O1i | 0.95 | 2.39 | 3.2753 (17) | 155 |
C19—H19B···Cg1ii | 0.98 | 2.87 | 3.4276 (17) | 117 |
Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) −x+1, y−1/2, −z+3/2. |
C19H20Cl2N2 | Z = 4 |
Mr = 347.27 | F(000) = 728 |
Triclinic, P1 | Dx = 1.295 Mg m−3 |
a = 9.8352 (2) Å | Cu Kα radiation, λ = 1.54184 Å |
b = 11.8401 (2) Å | Cell parameters from 36250 reflections |
c = 16.3964 (2) Å | θ = 2.7–77.7° |
α = 98.397 (1)° | µ = 3.27 mm−1 |
β = 96.189 (1)° | T = 100 K |
γ = 107.149 (1)° | Prism, red |
V = 1781.77 (5) Å3 | 0.25 × 0.22 × 0.18 mm |
XtaLAB Synergy, Dualflex, HyPix diffractometer | 6948 reflections with I > 2σ(I) |
Radiation source: micro-focus sealed X-ray tube | Rint = 0.071 |
φ and ω scans | θmax = 77.9°, θmin = 2.8° |
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2021) | h = −12→12 |
Tmin = 0.328, Tmax = 0.550 | k = −14→12 |
53607 measured reflections | l = −20→20 |
7515 independent reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.058 | H-atom parameters constrained |
wR(F2) = 0.171 | w = 1/[σ2(Fo2) + (0.1247P)2 + 0.6991P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
7515 reflections | Δρmax = 0.93 e Å−3 |
423 parameters | Δρmin = −0.63 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 | 0.61178 (18) | 0.35073 (16) | 0.16342 (12) | 0.0249 (4) | |
C2 | 0.6208 (2) | 0.27286 (17) | 0.09726 (12) | 0.0286 (4) | |
C3 | 0.58777 (18) | 0.31800 (15) | 0.24597 (11) | 0.0230 (3) | |
C4 | 0.46666 (19) | 0.32673 (16) | 0.28085 (12) | 0.0265 (4) | |
H4 | 0.393723 | 0.347551 | 0.249429 | 0.032* | |
C5 | 0.45226 (19) | 0.30530 (16) | 0.36066 (12) | 0.0265 (4) | |
H5 | 0.369067 | 0.311600 | 0.383040 | 0.032* | |
C6 | 0.55770 (18) | 0.27437 (15) | 0.40967 (11) | 0.0239 (3) | |
C7 | 0.67636 (19) | 0.26365 (16) | 0.37312 (12) | 0.0255 (4) | |
H7 | 0.748785 | 0.241541 | 0.403958 | 0.031* | |
C8 | 0.69106 (18) | 0.28451 (16) | 0.29288 (12) | 0.0255 (4) | |
H8 | 0.772654 | 0.275817 | 0.269671 | 0.031* | |
C9 | 0.5398 (2) | 0.25476 (16) | 0.49849 (12) | 0.0272 (4) | |
C10 | 0.5205 (2) | 0.36724 (18) | 0.54994 (13) | 0.0333 (4) | |
H10A | 0.603703 | 0.437581 | 0.550108 | 0.050* | |
H10B | 0.512989 | 0.355418 | 0.607413 | 0.050* | |
H10C | 0.432478 | 0.380217 | 0.525009 | 0.050* | |
C11 | 0.4060 (2) | 0.14560 (18) | 0.49507 (13) | 0.0344 (4) | |
H11A | 0.320435 | 0.160683 | 0.468623 | 0.052* | |
H11B | 0.394079 | 0.132610 | 0.551906 | 0.052* | |
H11C | 0.418147 | 0.073943 | 0.462518 | 0.052* | |
C12 | 0.6708 (2) | 0.2312 (2) | 0.54356 (13) | 0.0343 (4) | |
H12A | 0.681949 | 0.157211 | 0.513836 | 0.051* | |
H12B | 0.656545 | 0.222374 | 0.600823 | 0.051* | |
H12C | 0.757630 | 0.298939 | 0.544841 | 0.051* | |
C13 | 0.67080 (18) | 0.66543 (17) | 0.20121 (12) | 0.0267 (4) | |
C14 | 0.67993 (19) | 0.69894 (17) | 0.12348 (12) | 0.0273 (4) | |
H14 | 0.659272 | 0.638881 | 0.074597 | 0.033* | |
C15 | 0.7192 (2) | 0.81996 (18) | 0.11699 (13) | 0.0300 (4) | |
C16 | 0.7485 (2) | 0.90601 (17) | 0.18984 (13) | 0.0313 (4) | |
H16 | 0.776188 | 0.988838 | 0.186220 | 0.038* | |
C17 | 0.7382 (2) | 0.87368 (18) | 0.26740 (13) | 0.0313 (4) | |
H17 | 0.757830 | 0.933887 | 0.316095 | 0.038* | |
C18 | 0.69929 (19) | 0.75318 (17) | 0.27368 (13) | 0.0284 (4) | |
H18 | 0.691972 | 0.730266 | 0.326601 | 0.034* | |
C19 | 0.7313 (3) | 0.85617 (19) | 0.03339 (14) | 0.0372 (5) | |
H19A | 0.681665 | 0.915895 | 0.027531 | 0.056* | |
H19B | 0.686864 | 0.785258 | −0.010902 | 0.056* | |
H19C | 0.833165 | 0.891001 | 0.028971 | 0.056* | |
C20 | 0.91894 (19) | 0.62019 (16) | 0.82034 (12) | 0.0257 (4) | |
C21 | 0.9535 (2) | 0.69058 (16) | 0.89645 (12) | 0.0290 (4) | |
C22 | 0.87259 (19) | 0.48653 (16) | 0.80936 (11) | 0.0237 (3) | |
C23 | 0.72883 (19) | 0.41702 (17) | 0.79251 (12) | 0.0278 (4) | |
H23 | 0.656334 | 0.454890 | 0.787674 | 0.033* | |
C24 | 0.68937 (18) | 0.29242 (16) | 0.78259 (12) | 0.0261 (4) | |
H24 | 0.589993 | 0.246660 | 0.771607 | 0.031* | |
C25 | 0.79213 (18) | 0.23299 (15) | 0.78837 (11) | 0.0228 (3) | |
C26 | 0.93658 (19) | 0.30439 (17) | 0.80626 (12) | 0.0286 (4) | |
H26 | 1.009196 | 0.266638 | 0.811020 | 0.034* | |
C27 | 0.97708 (19) | 0.42862 (17) | 0.81727 (13) | 0.0292 (4) | |
H27 | 1.076283 | 0.474732 | 0.830261 | 0.035* | |
C28 | 0.75234 (19) | 0.09595 (16) | 0.77649 (11) | 0.0253 (4) | |
C29 | 0.5908 (2) | 0.03328 (16) | 0.74827 (13) | 0.0306 (4) | |
H29A | 0.537672 | 0.059455 | 0.790546 | 0.046* | |
H29B | 0.570431 | −0.054050 | 0.741081 | 0.046* | |
H29C | 0.560719 | 0.054255 | 0.695097 | 0.046* | |
C30 | 0.8320 (2) | 0.05048 (18) | 0.70974 (14) | 0.0341 (4) | |
H30A | 0.808999 | 0.077558 | 0.657793 | 0.051* | |
H30B | 0.801615 | −0.037641 | 0.699604 | 0.051* | |
H30C | 0.936143 | 0.082550 | 0.729276 | 0.051* | |
C31 | 0.7981 (2) | 0.06146 (18) | 0.85985 (14) | 0.0369 (5) | |
H31A | 0.902082 | 0.099535 | 0.877774 | 0.055* | |
H31B | 0.774929 | −0.026150 | 0.852401 | 0.055* | |
H31C | 0.746315 | 0.089054 | 0.902386 | 0.055* | |
C32 | 0.92807 (19) | 0.68230 (17) | 0.61640 (12) | 0.0254 (4) | |
C33 | 0.90203 (19) | 0.61415 (17) | 0.53664 (12) | 0.0279 (4) | |
H33 | 0.868253 | 0.528857 | 0.529137 | 0.034* | |
C34 | 0.9247 (2) | 0.66907 (18) | 0.46696 (12) | 0.0293 (4) | |
C35 | 0.9724 (2) | 0.79377 (18) | 0.48010 (13) | 0.0310 (4) | |
H35 | 0.988008 | 0.832852 | 0.433702 | 0.037* | |
C36 | 0.9977 (2) | 0.86290 (18) | 0.55985 (13) | 0.0328 (4) | |
H36 | 1.029797 | 0.948185 | 0.567020 | 0.039* | |
C37 | 0.9767 (2) | 0.80869 (17) | 0.62886 (12) | 0.0293 (4) | |
H37 | 0.994786 | 0.855806 | 0.683334 | 0.035* | |
C38 | 0.8987 (3) | 0.5940 (2) | 0.38145 (13) | 0.0393 (5) | |
H38A | 0.955999 | 0.538846 | 0.381276 | 0.059* | |
H38B | 0.926960 | 0.646511 | 0.341058 | 0.059* | |
H38C | 0.796204 | 0.547539 | 0.366089 | 0.059* | |
Cl1 | 0.58942 (6) | 0.12256 (4) | 0.09905 (3) | 0.03558 (15) | |
Cl2 | 0.66274 (6) | 0.31202 (5) | 0.00425 (3) | 0.03661 (15) | |
Cl3 | 0.93882 (6) | 0.63467 (4) | 0.98652 (3) | 0.03543 (15) | |
Cl4 | 1.01859 (6) | 0.84553 (4) | 0.91208 (3) | 0.03931 (16) | |
N1 | 0.63865 (16) | 0.47049 (14) | 0.15050 (10) | 0.0266 (3) | |
N2 | 0.63619 (16) | 0.54441 (14) | 0.21407 (10) | 0.0260 (3) | |
N3 | 0.93773 (17) | 0.68198 (14) | 0.75331 (10) | 0.0269 (3) | |
N4 | 0.90357 (16) | 0.61543 (14) | 0.68230 (10) | 0.0264 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0242 (8) | 0.0224 (8) | 0.0308 (9) | 0.0099 (6) | 0.0048 (6) | 0.0082 (7) |
C2 | 0.0314 (9) | 0.0264 (9) | 0.0314 (9) | 0.0123 (7) | 0.0071 (7) | 0.0083 (7) |
C3 | 0.0257 (8) | 0.0165 (7) | 0.0286 (9) | 0.0091 (6) | 0.0043 (6) | 0.0050 (6) |
C4 | 0.0261 (8) | 0.0235 (9) | 0.0346 (9) | 0.0135 (7) | 0.0045 (7) | 0.0085 (7) |
C5 | 0.0254 (8) | 0.0246 (9) | 0.0339 (10) | 0.0126 (7) | 0.0073 (7) | 0.0075 (7) |
C6 | 0.0260 (8) | 0.0180 (8) | 0.0289 (9) | 0.0088 (6) | 0.0043 (7) | 0.0047 (6) |
C7 | 0.0256 (8) | 0.0229 (8) | 0.0308 (9) | 0.0113 (6) | 0.0035 (7) | 0.0075 (7) |
C8 | 0.0232 (8) | 0.0231 (8) | 0.0339 (9) | 0.0116 (6) | 0.0058 (7) | 0.0067 (7) |
C9 | 0.0302 (9) | 0.0251 (9) | 0.0286 (9) | 0.0109 (7) | 0.0061 (7) | 0.0065 (7) |
C10 | 0.0399 (10) | 0.0312 (10) | 0.0331 (10) | 0.0164 (8) | 0.0101 (8) | 0.0048 (8) |
C11 | 0.0365 (10) | 0.0300 (10) | 0.0355 (10) | 0.0056 (8) | 0.0084 (8) | 0.0102 (8) |
C12 | 0.0386 (10) | 0.0387 (11) | 0.0311 (10) | 0.0184 (8) | 0.0056 (8) | 0.0107 (8) |
C13 | 0.0223 (8) | 0.0256 (9) | 0.0354 (10) | 0.0103 (7) | 0.0055 (7) | 0.0093 (7) |
C14 | 0.0268 (8) | 0.0248 (9) | 0.0329 (9) | 0.0121 (7) | 0.0042 (7) | 0.0057 (7) |
C15 | 0.0276 (8) | 0.0309 (10) | 0.0346 (10) | 0.0117 (7) | 0.0048 (7) | 0.0109 (8) |
C16 | 0.0284 (9) | 0.0236 (9) | 0.0430 (11) | 0.0100 (7) | 0.0040 (8) | 0.0075 (8) |
C17 | 0.0306 (9) | 0.0262 (9) | 0.0367 (10) | 0.0113 (7) | 0.0027 (7) | 0.0013 (7) |
C18 | 0.0267 (8) | 0.0266 (9) | 0.0344 (10) | 0.0118 (7) | 0.0044 (7) | 0.0064 (7) |
C19 | 0.0501 (12) | 0.0270 (10) | 0.0386 (11) | 0.0146 (9) | 0.0089 (9) | 0.0129 (8) |
C20 | 0.0255 (8) | 0.0235 (9) | 0.0303 (9) | 0.0093 (7) | 0.0070 (7) | 0.0070 (7) |
C21 | 0.0361 (9) | 0.0206 (8) | 0.0327 (10) | 0.0097 (7) | 0.0094 (7) | 0.0082 (7) |
C22 | 0.0280 (8) | 0.0214 (8) | 0.0237 (8) | 0.0101 (7) | 0.0059 (6) | 0.0048 (6) |
C23 | 0.0270 (8) | 0.0233 (9) | 0.0364 (10) | 0.0137 (7) | 0.0045 (7) | 0.0048 (7) |
C24 | 0.0214 (8) | 0.0232 (9) | 0.0344 (9) | 0.0086 (6) | 0.0033 (7) | 0.0053 (7) |
C25 | 0.0269 (8) | 0.0221 (8) | 0.0224 (8) | 0.0117 (7) | 0.0042 (6) | 0.0048 (6) |
C26 | 0.0254 (8) | 0.0271 (9) | 0.0371 (10) | 0.0145 (7) | 0.0039 (7) | 0.0056 (7) |
C27 | 0.0217 (8) | 0.0260 (9) | 0.0398 (10) | 0.0076 (7) | 0.0048 (7) | 0.0059 (7) |
C28 | 0.0287 (8) | 0.0212 (8) | 0.0287 (9) | 0.0120 (7) | 0.0035 (7) | 0.0052 (6) |
C29 | 0.0303 (9) | 0.0197 (8) | 0.0417 (11) | 0.0071 (7) | 0.0063 (8) | 0.0059 (7) |
C30 | 0.0329 (9) | 0.0263 (9) | 0.0426 (11) | 0.0127 (7) | 0.0069 (8) | −0.0026 (8) |
C31 | 0.0492 (12) | 0.0264 (10) | 0.0375 (11) | 0.0158 (8) | −0.0009 (9) | 0.0112 (8) |
C32 | 0.0246 (8) | 0.0269 (9) | 0.0293 (9) | 0.0130 (7) | 0.0054 (7) | 0.0086 (7) |
C33 | 0.0278 (8) | 0.0237 (9) | 0.0336 (10) | 0.0113 (7) | 0.0020 (7) | 0.0050 (7) |
C34 | 0.0298 (9) | 0.0309 (10) | 0.0300 (9) | 0.0159 (7) | 0.0008 (7) | 0.0041 (7) |
C35 | 0.0352 (9) | 0.0308 (10) | 0.0324 (10) | 0.0168 (8) | 0.0052 (7) | 0.0100 (7) |
C36 | 0.0411 (10) | 0.0254 (9) | 0.0351 (10) | 0.0147 (8) | 0.0052 (8) | 0.0078 (8) |
C37 | 0.0340 (9) | 0.0263 (9) | 0.0315 (9) | 0.0154 (7) | 0.0052 (7) | 0.0053 (7) |
C38 | 0.0563 (13) | 0.0344 (11) | 0.0305 (10) | 0.0231 (10) | −0.0010 (9) | 0.0040 (8) |
Cl1 | 0.0505 (3) | 0.0238 (3) | 0.0367 (3) | 0.0175 (2) | 0.0099 (2) | 0.00496 (19) |
Cl2 | 0.0483 (3) | 0.0372 (3) | 0.0302 (3) | 0.0181 (2) | 0.0131 (2) | 0.01026 (19) |
Cl3 | 0.0526 (3) | 0.0272 (3) | 0.0286 (3) | 0.0135 (2) | 0.0108 (2) | 0.00704 (18) |
Cl4 | 0.0583 (3) | 0.0196 (2) | 0.0377 (3) | 0.0078 (2) | 0.0127 (2) | 0.00383 (18) |
N1 | 0.0252 (7) | 0.0249 (8) | 0.0330 (8) | 0.0104 (6) | 0.0055 (6) | 0.0099 (6) |
N2 | 0.0246 (7) | 0.0228 (7) | 0.0335 (8) | 0.0108 (6) | 0.0052 (6) | 0.0072 (6) |
N3 | 0.0290 (7) | 0.0252 (8) | 0.0299 (8) | 0.0114 (6) | 0.0074 (6) | 0.0079 (6) |
N4 | 0.0253 (7) | 0.0259 (8) | 0.0311 (8) | 0.0116 (6) | 0.0044 (6) | 0.0079 (6) |
C1—C2 | 1.346 (3) | C20—N3 | 1.406 (2) |
C1—N1 | 1.416 (2) | C20—C22 | 1.489 (2) |
C1—C3 | 1.485 (2) | C21—Cl3 | 1.7074 (19) |
C2—Cl2 | 1.715 (2) | C21—Cl4 | 1.7252 (19) |
C2—Cl1 | 1.7193 (19) | C22—C23 | 1.384 (3) |
C3—C8 | 1.392 (2) | C22—C27 | 1.399 (2) |
C3—C4 | 1.400 (2) | C23—C24 | 1.390 (3) |
C4—C5 | 1.383 (3) | C23—H23 | 0.9500 |
C4—H4 | 0.9500 | C24—C25 | 1.394 (2) |
C5—C6 | 1.409 (2) | C24—H24 | 0.9500 |
C5—H5 | 0.9500 | C25—C26 | 1.396 (3) |
C6—C7 | 1.398 (2) | C25—C28 | 1.530 (2) |
C6—C9 | 1.528 (2) | C26—C27 | 1.384 (3) |
C7—C8 | 1.389 (3) | C26—H26 | 0.9500 |
C7—H7 | 0.9500 | C27—H27 | 0.9500 |
C8—H8 | 0.9500 | C28—C29 | 1.528 (2) |
C9—C12 | 1.533 (3) | C28—C30 | 1.537 (3) |
C9—C11 | 1.538 (3) | C28—C31 | 1.541 (3) |
C9—C10 | 1.542 (3) | C29—H29A | 0.9800 |
C10—H10A | 0.9800 | C29—H29B | 0.9800 |
C10—H10B | 0.9800 | C29—H29C | 0.9800 |
C10—H10C | 0.9800 | C30—H30A | 0.9800 |
C11—H11A | 0.9800 | C30—H30B | 0.9800 |
C11—H11B | 0.9800 | C30—H30C | 0.9800 |
C11—H11C | 0.9800 | C31—H31A | 0.9800 |
C12—H12A | 0.9800 | C31—H31B | 0.9800 |
C12—H12B | 0.9800 | C31—H31C | 0.9800 |
C12—H12C | 0.9800 | C32—C33 | 1.387 (3) |
C13—C14 | 1.393 (3) | C32—C37 | 1.406 (3) |
C13—C18 | 1.402 (3) | C32—N4 | 1.430 (2) |
C13—N2 | 1.425 (2) | C33—C34 | 1.402 (3) |
C14—C15 | 1.393 (3) | C33—H33 | 0.9500 |
C14—H14 | 0.9500 | C34—C35 | 1.387 (3) |
C15—C16 | 1.395 (3) | C34—C38 | 1.499 (3) |
C15—C19 | 1.501 (3) | C35—C36 | 1.392 (3) |
C16—C17 | 1.386 (3) | C35—H35 | 0.9500 |
C16—H16 | 0.9500 | C36—C37 | 1.385 (3) |
C17—C18 | 1.386 (3) | C36—H36 | 0.9500 |
C17—H17 | 0.9500 | C37—H37 | 0.9500 |
C18—H18 | 0.9500 | C38—H38A | 0.9800 |
C19—H19A | 0.9800 | C38—H38B | 0.9800 |
C19—H19B | 0.9800 | C38—H38C | 0.9800 |
C19—H19C | 0.9800 | N1—N2 | 1.267 (2) |
C20—C21 | 1.344 (3) | N3—N4 | 1.257 (2) |
C2—C1—N1 | 114.51 (16) | N3—C20—C22 | 123.14 (16) |
C2—C1—C3 | 123.57 (16) | C20—C21—Cl3 | 123.03 (15) |
N1—C1—C3 | 121.73 (16) | C20—C21—Cl4 | 123.05 (15) |
C1—C2—Cl2 | 124.11 (15) | Cl3—C21—Cl4 | 113.91 (11) |
C1—C2—Cl1 | 122.10 (15) | C23—C22—C27 | 118.47 (16) |
Cl2—C2—Cl1 | 113.79 (11) | C23—C22—C20 | 122.24 (16) |
C8—C3—C4 | 118.29 (17) | C27—C22—C20 | 119.28 (16) |
C8—C3—C1 | 120.08 (15) | C22—C23—C24 | 120.73 (16) |
C4—C3—C1 | 121.52 (15) | C22—C23—H23 | 119.6 |
C5—C4—C3 | 120.57 (16) | C24—C23—H23 | 119.6 |
C5—C4—H4 | 119.7 | C23—C24—C25 | 121.58 (16) |
C3—C4—H4 | 119.7 | C23—C24—H24 | 119.2 |
C4—C5—C6 | 121.76 (16) | C25—C24—H24 | 119.2 |
C4—C5—H5 | 119.1 | C24—C25—C26 | 117.00 (16) |
C6—C5—H5 | 119.1 | C24—C25—C28 | 122.87 (15) |
C7—C6—C5 | 116.83 (16) | C26—C25—C28 | 120.13 (15) |
C7—C6—C9 | 123.00 (15) | C27—C26—C25 | 121.91 (16) |
C5—C6—C9 | 120.17 (16) | C27—C26—H26 | 119.0 |
C8—C7—C6 | 121.65 (16) | C25—C26—H26 | 119.0 |
C8—C7—H7 | 119.2 | C26—C27—C22 | 120.28 (16) |
C6—C7—H7 | 119.2 | C26—C27—H27 | 119.9 |
C7—C8—C3 | 120.87 (16) | C22—C27—H27 | 119.9 |
C7—C8—H8 | 119.6 | C29—C28—C25 | 112.29 (14) |
C3—C8—H8 | 119.6 | C29—C28—C30 | 107.92 (15) |
C6—C9—C12 | 112.17 (15) | C25—C28—C30 | 109.58 (15) |
C6—C9—C11 | 109.16 (15) | C29—C28—C31 | 108.82 (16) |
C12—C9—C11 | 108.39 (16) | C25—C28—C31 | 109.01 (15) |
C6—C9—C10 | 109.85 (15) | C30—C28—C31 | 109.17 (16) |
C12—C9—C10 | 107.88 (16) | C28—C29—H29A | 109.5 |
C11—C9—C10 | 109.34 (16) | C28—C29—H29B | 109.5 |
C9—C10—H10A | 109.5 | H29A—C29—H29B | 109.5 |
C9—C10—H10B | 109.5 | C28—C29—H29C | 109.5 |
H10A—C10—H10B | 109.5 | H29A—C29—H29C | 109.5 |
C9—C10—H10C | 109.5 | H29B—C29—H29C | 109.5 |
H10A—C10—H10C | 109.5 | C28—C30—H30A | 109.5 |
H10B—C10—H10C | 109.5 | C28—C30—H30B | 109.5 |
C9—C11—H11A | 109.5 | H30A—C30—H30B | 109.5 |
C9—C11—H11B | 109.5 | C28—C30—H30C | 109.5 |
H11A—C11—H11B | 109.5 | H30A—C30—H30C | 109.5 |
C9—C11—H11C | 109.5 | H30B—C30—H30C | 109.5 |
H11A—C11—H11C | 109.5 | C28—C31—H31A | 109.5 |
H11B—C11—H11C | 109.5 | C28—C31—H31B | 109.5 |
C9—C12—H12A | 109.5 | H31A—C31—H31B | 109.5 |
C9—C12—H12B | 109.5 | C28—C31—H31C | 109.5 |
H12A—C12—H12B | 109.5 | H31A—C31—H31C | 109.5 |
C9—C12—H12C | 109.5 | H31B—C31—H31C | 109.5 |
H12A—C12—H12C | 109.5 | C33—C32—C37 | 120.41 (17) |
H12B—C12—H12C | 109.5 | C33—C32—N4 | 115.61 (16) |
C14—C13—C18 | 120.31 (17) | C37—C32—N4 | 123.98 (17) |
C14—C13—N2 | 124.27 (17) | C32—C33—C34 | 121.09 (17) |
C18—C13—N2 | 115.41 (17) | C32—C33—H33 | 119.5 |
C15—C14—C13 | 120.41 (18) | C34—C33—H33 | 119.5 |
C15—C14—H14 | 119.8 | C35—C34—C33 | 117.91 (18) |
C13—C14—H14 | 119.8 | C35—C34—C38 | 121.73 (18) |
C14—C15—C16 | 118.46 (18) | C33—C34—C38 | 120.36 (18) |
C14—C15—C19 | 120.42 (18) | C34—C35—C36 | 121.39 (18) |
C16—C15—C19 | 121.12 (18) | C34—C35—H35 | 119.3 |
C17—C16—C15 | 121.63 (18) | C36—C35—H35 | 119.3 |
C17—C16—H16 | 119.2 | C37—C36—C35 | 120.73 (18) |
C15—C16—H16 | 119.2 | C37—C36—H36 | 119.6 |
C16—C17—C18 | 119.78 (18) | C35—C36—H36 | 119.6 |
C16—C17—H17 | 120.1 | C36—C37—C32 | 118.46 (18) |
C18—C17—H17 | 120.1 | C36—C37—H37 | 120.8 |
C17—C18—C13 | 119.40 (18) | C32—C37—H37 | 120.8 |
C17—C18—H18 | 120.3 | C34—C38—H38A | 109.5 |
C13—C18—H18 | 120.3 | C34—C38—H38B | 109.5 |
C15—C19—H19A | 109.5 | H38A—C38—H38B | 109.5 |
C15—C19—H19B | 109.5 | C34—C38—H38C | 109.5 |
H19A—C19—H19B | 109.5 | H38A—C38—H38C | 109.5 |
C15—C19—H19C | 109.5 | H38B—C38—H38C | 109.5 |
H19A—C19—H19C | 109.5 | N2—N1—C1 | 114.26 (15) |
H19B—C19—H19C | 109.5 | N1—N2—C13 | 113.47 (16) |
C21—C20—N3 | 115.13 (16) | N4—N3—C20 | 114.67 (16) |
C21—C20—C22 | 121.64 (16) | N3—N4—C32 | 112.53 (15) |
N1—C1—C2—Cl2 | 0.6 (2) | N3—C20—C22—C23 | −86.1 (2) |
C3—C1—C2—Cl2 | −174.56 (13) | C21—C20—C22—C27 | −81.6 (2) |
N1—C1—C2—Cl1 | −178.98 (13) | N3—C20—C22—C27 | 94.7 (2) |
C3—C1—C2—Cl1 | 5.9 (3) | C27—C22—C23—C24 | −0.8 (3) |
C2—C1—C3—C8 | 64.6 (2) | C20—C22—C23—C24 | 179.97 (17) |
N1—C1—C3—C8 | −110.21 (19) | C22—C23—C24—C25 | −0.6 (3) |
C2—C1—C3—C4 | −119.3 (2) | C23—C24—C25—C26 | 1.3 (3) |
N1—C1—C3—C4 | 65.9 (2) | C23—C24—C25—C28 | −179.07 (17) |
C8—C3—C4—C5 | 1.5 (3) | C24—C25—C26—C27 | −0.5 (3) |
C1—C3—C4—C5 | −174.67 (16) | C28—C25—C26—C27 | 179.86 (17) |
C3—C4—C5—C6 | 0.1 (3) | C25—C26—C27—C22 | −1.0 (3) |
C4—C5—C6—C7 | −1.4 (3) | C23—C22—C27—C26 | 1.6 (3) |
C4—C5—C6—C9 | 178.32 (16) | C20—C22—C27—C26 | −179.16 (17) |
C5—C6—C7—C8 | 1.1 (3) | C24—C25—C28—C29 | 6.5 (2) |
C9—C6—C7—C8 | −178.62 (16) | C26—C25—C28—C29 | −173.87 (17) |
C6—C7—C8—C3 | 0.5 (3) | C24—C25—C28—C30 | 126.39 (19) |
C4—C3—C8—C7 | −1.8 (3) | C26—C25—C28—C30 | −54.0 (2) |
C1—C3—C8—C7 | 174.42 (16) | C24—C25—C28—C31 | −114.2 (2) |
C7—C6—C9—C12 | 4.0 (2) | C26—C25—C28—C31 | 65.5 (2) |
C5—C6—C9—C12 | −175.72 (17) | C37—C32—C33—C34 | 0.6 (3) |
C7—C6—C9—C11 | −116.16 (19) | N4—C32—C33—C34 | −178.73 (16) |
C5—C6—C9—C11 | 64.1 (2) | C32—C33—C34—C35 | −0.8 (3) |
C7—C6—C9—C10 | 123.96 (18) | C32—C33—C34—C38 | 178.83 (18) |
C5—C6—C9—C10 | −55.7 (2) | C33—C34—C35—C36 | 0.3 (3) |
C18—C13—C14—C15 | 0.8 (3) | C38—C34—C35—C36 | −179.32 (19) |
N2—C13—C14—C15 | −177.87 (16) | C34—C35—C36—C37 | 0.4 (3) |
C13—C14—C15—C16 | −0.2 (3) | C35—C36—C37—C32 | −0.5 (3) |
C13—C14—C15—C19 | 179.04 (17) | C33—C32—C37—C36 | 0.0 (3) |
C14—C15—C16—C17 | −0.6 (3) | N4—C32—C37—C36 | 179.35 (17) |
C19—C15—C16—C17 | −179.74 (18) | C2—C1—N1—N2 | −177.09 (16) |
C15—C16—C17—C18 | 0.6 (3) | C3—C1—N1—N2 | −1.8 (2) |
C16—C17—C18—C13 | 0.0 (3) | C1—N1—N2—C13 | 176.92 (14) |
C14—C13—C18—C17 | −0.7 (3) | C14—C13—N2—N1 | 11.6 (2) |
N2—C13—C18—C17 | 178.04 (16) | C18—C13—N2—N1 | −167.08 (15) |
N3—C20—C21—Cl3 | 179.92 (13) | C21—C20—N3—N4 | −179.22 (16) |
C22—C20—C21—Cl3 | −3.5 (3) | C22—C20—N3—N4 | 4.3 (2) |
N3—C20—C21—Cl4 | −0.8 (2) | C20—N3—N4—C32 | −178.50 (14) |
C22—C20—C21—Cl4 | 175.73 (13) | C33—C32—N4—N3 | 175.76 (15) |
C21—C20—C22—C23 | 97.6 (2) | C37—C32—N4—N3 | −3.6 (2) |
Cg1 and Cg2 are the centroids of the 4-tert-butylphenyl rings [(IVA: C3–C8 and (IVB): C22–C27, respectively]. Cg4 is the centroid of the 3-methylphenyl ring (C32–C37) of molecule (IVB). |
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7···Cg4i | 0.95 | 2.91 | 3.768 (2) | 151 |
C24—H24···Cg2ii | 0.95 | 2.97 | 3.824 (2) | 150 |
C29—H29B···Cg1iii | 0.98 | 2.78 | 3.706 (2) | 157 |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y, −z+1. |
Contact | Percentage contribution | ||||
(I) | (II) | (III) | (IVA) | (IVB) | |
H···H | 45.3 | 47.1 | 43.6 | 47.0 | 44.2 |
Cl···H/H···Cl | 22.8 | 22.2 | 21.3 | 20.1 | 19.8 |
C···H/H···C | 17.5 | 18.6 | 17.0 | 20.7 | 21.1 |
N···H/H···N | 5.3 | 5.8 | 3.7 | 7.2 | 8.3 |
O···H/H···O | – | – | 5.1 | – | – |
Cl···C/C···Cl | 3.2 | 2.8 | 2.7 | 2.4 | 3.3 |
C···C | 2.4 | 1.2 | 1.7 | 0.3 | 0.3 |
N···C/C···N | 1.5 | 0.7 | 1.4 | – | – |
Cl···N/N···Cl | 1.2 | 0.5 | 2.9 | – | – |
Cl···Cl | 0.8 | 1.2 | 0.6 | 2.3 | 3.0 |
Acknowledgements
The authors' contributions are as follows. Conceptualization, MA, NQS and AB; synthesis, AM, AQ, GTA and AN; X-ray analysis, VNK, MA, and SÖY; writing (review and editing of the manuscript) MA, NQS and AB; funding acquisition, AM and NQS; supervision, MA and AB.
Funding information
This work was performed under the support of the Science Development Foundation under the President of the Republic of Azerbaijan (grant No. EIF-BGM-4- RFTF-1/2017–21/13/4).
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