In the title compound, the indazole ring system is oriented at dihedral angles of 25.04 (4) and 5.10 (4)° o the furan and benzene rings, respectively
Keywords: crystal structure, furan, indazole, C—H⋯O interactions, π–π stacking
Abstract
In the title compound, C20H16Cl2N2O2, the indazole ring system is approximately planar [maximum deviation = 0.033 (1) Å], its mean plane is oriented at dihedral angles of 25.04 (4) and 5.10 (4)° to the furan and benzene rings, respectively. In the crystal, pairs of C—Hind⋯Obo (ind = indazole and bo = benzyloxy) hydrogen bonds link the molecules into centrosymmetric dimers with graph-set motif R 2 2(12). Weak C—H⋯π interactions is also observed. Aromatic π–π stacking between the benzene and the pyrazole rings from neighbouring molecules [centroid–centroid distance = 3.8894 (7) Å] further consolidates the crystal packing.
Chemical context
Ethers such as miconazole and econazole possessing an imidazole ring have been developed for clinical uses as azole antifungals (Godefroi et al., 1969 ▸). The crystal structures of miconazole (Peeters et al., 1979 ▸) and econazole (Freer et al., 1986 ▸) have previously been reported. Another azole ring system, indazole, is an important structural unit of many biologically active compounds. Some indazole derivatives have been shown to exhibit antifungal (Lebouvier et al., 2007 ▸; Park et al., 2007 ▸), antibacterial (Wang et al., 2015 ▸), antiproliferative (Büchel et al., 2012 ▸), antitumor (Abbassi et al., 2014 ▸) activity and act as inhibitors of nitric oxide synthase with antioxidant properties (Salerno et al., 2012 ▸). The crystal structures of some indazole derivatives have been reported (Gerpe et al., 2007 ▸; Raffa et al., 2009 ▸; Boulhaoua et al., 2015 ▸). In addition, the crystal structures of ketones containing an indazole group (Özel Güven et al., 2013 ▸, 2014a
▸) and ether (Özel Güven et al., 2014b
▸) have been described. As a continuation of our studies in this area, we synthesized the title compound and report herein its crystal structure.
Structural commentary
In the molecule of the title compound, (Fig. 1 ▸), the bond lengths and angles are within normal ranges. The indazole (B; N1/N2/C7–C13) ring system is approximately planar with a maximum deviation of −0.033 (1) Å for atom C10. Its mean plane is oriented with respect to the furan (A; O2/C2–C5) and benzene (C; C15–C20) rings at dihedral angles of A/B = 25.04 (4) and B/C = 5.10 (4)°. The dihedral angle between the furan and benzene rings is 20.21 (5)°. Atom C6 is −0.054 (1) Å from the indazole ring plane, while atom C1 is 0.038 (1) Å from the furan ring plane. Atoms Cl1, Cl2 and C14 are displaced by −0.0430 (3), 0.0233 (4) and −0.016 (1) Å, respectively, to the benzene ring plane.
Figure 1.
The molecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
Supramolecular features
In the crystal, pairs of C—Hind⋯ Obo (ind = indazole and bo = benzyloxy) hydrogen bonds (Table 1 ▸), enclosing 
(12) ring motifs link the molecules into centrosymmetric dimers (Fig. 2 ▸), which are stacked along the a axis and oriented along the b-axis direction (Fig. 3 ▸). Weak C—H⋯π interactions (Table 1 ▸) occur. π–π interactions between the pyrazole and the benzene rings, Cg4⋯Cg3i, of neighbouring molecules further consolidate the crystal packing [centroid–centroid distance = 3.8894 (7) Å; symmetry code: (i) 2 − x, 2 − y, − z; Cg3 and Cg4 are the centroids of rings C (C15–C20) and D (N1/N2/C7/C8/C13)].
Table 1. Hydrogen-bond geometry (Å, °).
Cg4 is the centroid of the N1/N2/C7/C8/C13 ring.
| D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A |
|---|---|---|---|---|
| C7—H7⋯O1i | 0.93 | 2.51 | 3.3062 (15) | 144 |
| C6—H6B⋯Cg4ii | 0.97 | 2.84 | 3.4583 (13) | 122 |
Symmetry codes: (i) 
; (ii) 
.
Figure 2.
Part of the crystal structure. Intermolecular [C—Hind ⋯ Obo] hydrogen bonds, enclosing (12) ring motifs, are shown as dashed lines (see Table 1 ▸). H atoms not involved in hydrogen bonding have been omitted for clarity.
Figure 3.
The crystal packing of the title compound, viewed down the a axis. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted for clarity.
Synthesis and crystallization
The title compound was synthesized by the reaction of 1-(furan-2-yl)-2-(2H-indazol-2-yl)ethanol with NaH and 2,5-dichlorobenzyl bromide. NaH (16 mg, 0.394 mmol) was added in small fractions to a solution of alcohol (90 mg, 0.394 mmol) in DMF (3–4 ml). Then, 2,5-dichlorobenzyl bromide (95 mg, 0.394 mmol) was added portionwise. The mixture was stirred at room temperature for 3 h, and the excess hydride was decomposed with a small amount of methyl alcohol. After evaporation to dryness under reduced pressure, a small amount of water was added and extracted with methylene chloride. The organic layer was separated, dried over anhydrous sodium sulfate, and then evaporated to dryness. The crude residue was purified by chromatography on a silica-gel column using a hexane–ethyl acetate mixture (10:1) as eluent. The ether was recrystallized from 2-propanol solution to obtain colourless crystals suitable for X-ray analysis (yield; 70 mg, 46%).
Refinement
The experimental details including the crystal data, data collection and refinement are summarized in Table 2 ▸. The C-bound H atoms were positioned geometrically with C—H = 0.93, 0.97 and 0.98 Å, for aromatic, methylene and methine H-atoms, respectively, and constrained to ride on their parent atoms, with U iso(H) = 1.2U eq(C).
Table 2. Experimental details.
| Crystal data | |
| Chemical formula | C20H16Cl2N2O2 |
| M r | 387.27 |
| Crystal system, space group | Triclinic, P
|
| Temperature (K) | 294 |
| a, b, c (Å) | 7.7318 (3), 9.6675 (4), 12.8299 (5) |
| α, β, γ (°) | 76.511 (4), 76.157 (4), 73.928 (3) |
| V (Å3) | 880.30 (6) |
| Z | 2 |
| Radiation type | Mo Kα |
| μ (mm−1) | 0.39 |
| Crystal size (mm) | 0.09 × 0.07 × 0.04 |
| Data collection | |
| Diffractometer | Rigaku Saturn724+ |
| Absorption correction | Multi-scan (CrystalClear-SM Expert, Rigaku, 2011 ▸) |
| T min, T max | 0.968, 0.985 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 8400, 4278, 3813 |
| R int | 0.025 |
| (sin θ/λ)max (Å−1) | 0.674 |
| Refinement | |
| R[F 2 > 2σ(F 2)], wR(F 2), S | 0.031, 0.083, 1.05 |
| No. of reflections | 4278 |
| No. of parameters | 235 |
| H-atom treatment | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 0.35, −0.23 |
Supplementary Material
Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S2056989016013827/xu5891sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989016013827/xu5891Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989016013827/xu5891Isup3.cml
CCDC reference: 1501341
Additional supporting information: crystallographic information; 3D view; checkCIF report
Acknowledgments
The authors acknowledge the Zonguldak Karaelmas University Research Fund (project No. 2012-10-03-12) for support.
supplementary crystallographic information
Crystal data
| C20H16Cl2N2O2 | Z = 2 |
| Mr = 387.27 | F(000) = 400 |
| Triclinic, P1 | Dx = 1.461 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
| a = 7.7318 (3) Å | Cell parameters from 7516 reflections |
| b = 9.6675 (4) Å | θ = 3.0–28.6° |
| c = 12.8299 (5) Å | µ = 0.39 mm−1 |
| α = 76.511 (4)° | T = 294 K |
| β = 76.157 (4)° | Block, colorless |
| γ = 73.928 (3)° | 0.09 × 0.07 × 0.04 mm |
| V = 880.30 (6) Å3 |
Data collection
| Rigaku Saturn724+ diffractometer | 3813 reflections with I > 2σ(I) |
| Radiation source: fine-focus sealed tube | Rint = 0.025 |
| Graphite monochromator | θmax = 28.6°, θmin = 3.0° |
| ω scans | h = −6→10 |
| Absorption correction: multi-scan (CrystalClear-SM Expert, Rigaku, 2011) | k = −13→13 |
| Tmin = 0.968, Tmax = 0.985 | l = −17→17 |
| 8400 measured reflections | 3 standard reflections every 120 min |
| 4278 independent reflections | intensity decay: 1% |
Refinement
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.031 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.083 | H-atom parameters constrained |
| S = 1.05 | w = 1/[σ2(Fo2) + (0.0387P)2 + 0.3381P] where P = (Fo2 + 2Fc2)/3 |
| 4278 reflections | (Δ/σ)max = 0.001 |
| 235 parameters | Δρmax = 0.35 e Å−3 |
| 0 restraints | Δρmin = −0.23 e Å−3 |
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. |
| Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| Cl1 | 0.24682 (4) | 0.62858 (3) | 0.88313 (3) | 0.02337 (9) | |
| Cl2 | 0.49082 (5) | 0.22144 (3) | 0.53654 (2) | 0.02445 (9) | |
| O1 | 0.44963 (11) | 0.19772 (8) | 0.97438 (7) | 0.01525 (17) | |
| O2 | 0.31136 (12) | 0.14245 (9) | 1.21688 (7) | 0.02059 (19) | |
| N1 | 0.15767 (13) | 0.10240 (10) | 0.92745 (8) | 0.01489 (19) | |
| N2 | 0.03507 (13) | 0.21036 (11) | 0.87622 (8) | 0.0175 (2) | |
| C1 | 0.26260 (15) | 0.23752 (12) | 1.03067 (9) | 0.0143 (2) | |
| H1 | 0.1970 | 0.3262 | 0.9884 | 0.017* | |
| C2 | 0.25595 (15) | 0.26448 (13) | 1.14153 (9) | 0.0161 (2) | |
| C3 | 0.21044 (18) | 0.38619 (14) | 1.18630 (10) | 0.0211 (2) | |
| H3 | 0.1687 | 0.4820 | 1.1524 | 0.025* | |
| C4 | 0.23944 (19) | 0.33774 (15) | 1.29692 (11) | 0.0254 (3) | |
| H4 | 0.2204 | 0.3962 | 1.3487 | 0.031* | |
| C5 | 0.29944 (18) | 0.19136 (15) | 1.31093 (10) | 0.0236 (3) | |
| H5 | 0.3288 | 0.1316 | 1.3755 | 0.028* | |
| C6 | 0.17821 (16) | 0.11038 (12) | 1.03596 (9) | 0.0160 (2) | |
| H6A | 0.2559 | 0.0195 | 1.0659 | 0.019* | |
| H6B | 0.0592 | 0.1233 | 1.0839 | 0.019* | |
| C7 | 0.25036 (15) | −0.00406 (12) | 0.87016 (10) | 0.0156 (2) | |
| H7 | 0.3402 | −0.0856 | 0.8913 | 0.019* | |
| C8 | 0.18475 (15) | 0.03232 (12) | 0.77239 (10) | 0.0156 (2) | |
| C9 | 0.21674 (17) | −0.03471 (13) | 0.68025 (10) | 0.0188 (2) | |
| H9 | 0.3022 | −0.1232 | 0.6750 | 0.023* | |
| C10 | 0.11867 (17) | 0.03397 (14) | 0.59908 (10) | 0.0214 (2) | |
| H10 | 0.1362 | −0.0095 | 0.5387 | 0.026* | |
| C11 | −0.00995 (17) | 0.17116 (14) | 0.60570 (10) | 0.0222 (3) | |
| H11 | −0.0724 | 0.2161 | 0.5485 | 0.027* | |
| C12 | −0.04425 (17) | 0.23857 (13) | 0.69382 (10) | 0.0203 (2) | |
| H12 | −0.1283 | 0.3281 | 0.6970 | 0.024* | |
| C13 | 0.05251 (15) | 0.16753 (12) | 0.78018 (9) | 0.0158 (2) | |
| C14 | 0.51911 (16) | 0.32122 (12) | 0.91196 (9) | 0.0157 (2) | |
| H14A | 0.6518 | 0.2928 | 0.8940 | 0.019* | |
| H14B | 0.4856 | 0.3981 | 0.9550 | 0.019* | |
| C15 | 0.44190 (15) | 0.37805 (12) | 0.80800 (9) | 0.0149 (2) | |
| C16 | 0.32003 (16) | 0.51321 (12) | 0.78692 (10) | 0.0169 (2) | |
| C17 | 0.24998 (17) | 0.55987 (13) | 0.69043 (10) | 0.0204 (2) | |
| H17 | 0.1687 | 0.6505 | 0.6783 | 0.024* | |
| C18 | 0.30253 (17) | 0.47018 (14) | 0.61306 (10) | 0.0210 (2) | |
| H18 | 0.2581 | 0.5002 | 0.5482 | 0.025* | |
| C19 | 0.42271 (16) | 0.33464 (13) | 0.63373 (10) | 0.0180 (2) | |
| C20 | 0.49107 (16) | 0.28785 (13) | 0.72976 (9) | 0.0166 (2) | |
| H20 | 0.5699 | 0.1961 | 0.7422 | 0.020* |
Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Cl1 | 0.02851 (16) | 0.01783 (14) | 0.02403 (16) | 0.00089 (11) | −0.00838 (12) | −0.00825 (11) |
| Cl2 | 0.03293 (17) | 0.02802 (16) | 0.01613 (15) | −0.01132 (13) | −0.00224 (12) | −0.00855 (11) |
| O1 | 0.0145 (4) | 0.0151 (4) | 0.0142 (4) | −0.0024 (3) | −0.0014 (3) | −0.0015 (3) |
| O2 | 0.0261 (4) | 0.0211 (4) | 0.0132 (4) | −0.0024 (3) | −0.0051 (3) | −0.0027 (3) |
| N1 | 0.0148 (4) | 0.0151 (4) | 0.0151 (5) | −0.0031 (3) | −0.0037 (4) | −0.0026 (3) |
| N2 | 0.0166 (5) | 0.0168 (5) | 0.0189 (5) | −0.0014 (4) | −0.0057 (4) | −0.0032 (4) |
| C1 | 0.0144 (5) | 0.0148 (5) | 0.0129 (5) | −0.0022 (4) | −0.0021 (4) | −0.0026 (4) |
| C2 | 0.0151 (5) | 0.0191 (5) | 0.0135 (5) | −0.0041 (4) | −0.0026 (4) | −0.0016 (4) |
| C3 | 0.0253 (6) | 0.0211 (6) | 0.0184 (6) | −0.0050 (5) | −0.0049 (5) | −0.0060 (4) |
| C4 | 0.0312 (7) | 0.0310 (7) | 0.0177 (6) | −0.0082 (5) | −0.0044 (5) | −0.0105 (5) |
| C5 | 0.0263 (6) | 0.0324 (7) | 0.0125 (5) | −0.0060 (5) | −0.0049 (5) | −0.0045 (5) |
| C6 | 0.0182 (5) | 0.0168 (5) | 0.0134 (5) | −0.0049 (4) | −0.0028 (4) | −0.0027 (4) |
| C7 | 0.0152 (5) | 0.0146 (5) | 0.0172 (5) | −0.0032 (4) | −0.0032 (4) | −0.0033 (4) |
| C8 | 0.0143 (5) | 0.0159 (5) | 0.0169 (5) | −0.0053 (4) | −0.0020 (4) | −0.0023 (4) |
| C9 | 0.0196 (5) | 0.0195 (5) | 0.0187 (6) | −0.0059 (4) | −0.0021 (4) | −0.0058 (4) |
| C10 | 0.0222 (6) | 0.0268 (6) | 0.0183 (6) | −0.0083 (5) | −0.0034 (5) | −0.0071 (5) |
| C11 | 0.0225 (6) | 0.0273 (6) | 0.0187 (6) | −0.0061 (5) | −0.0093 (5) | −0.0018 (5) |
| C12 | 0.0186 (5) | 0.0201 (6) | 0.0219 (6) | −0.0027 (4) | −0.0067 (5) | −0.0026 (5) |
| C13 | 0.0150 (5) | 0.0168 (5) | 0.0163 (5) | −0.0050 (4) | −0.0025 (4) | −0.0030 (4) |
| C14 | 0.0158 (5) | 0.0163 (5) | 0.0154 (5) | −0.0047 (4) | −0.0030 (4) | −0.0024 (4) |
| C15 | 0.0143 (5) | 0.0164 (5) | 0.0148 (5) | −0.0058 (4) | −0.0021 (4) | −0.0022 (4) |
| C16 | 0.0186 (5) | 0.0158 (5) | 0.0167 (5) | −0.0046 (4) | −0.0032 (4) | −0.0034 (4) |
| C17 | 0.0225 (6) | 0.0180 (5) | 0.0201 (6) | −0.0039 (4) | −0.0075 (5) | 0.0000 (4) |
| C18 | 0.0251 (6) | 0.0246 (6) | 0.0149 (5) | −0.0093 (5) | −0.0069 (5) | 0.0009 (4) |
| C19 | 0.0201 (5) | 0.0216 (6) | 0.0140 (5) | −0.0094 (5) | −0.0004 (4) | −0.0042 (4) |
| C20 | 0.0169 (5) | 0.0169 (5) | 0.0161 (5) | −0.0053 (4) | −0.0020 (4) | −0.0026 (4) |
Geometric parameters (Å, º)
| Cl1—C16 | 1.7453 (12) | C8—C13 | 1.4269 (16) |
| Cl2—C19 | 1.7416 (12) | C9—C8 | 1.4169 (17) |
| O1—C1 | 1.4431 (13) | C9—C10 | 1.3699 (17) |
| O1—C14 | 1.4348 (13) | C9—H9 | 0.9300 |
| O2—C2 | 1.3770 (14) | C10—C11 | 1.4272 (18) |
| O2—C5 | 1.3701 (15) | C10—H10 | 0.9300 |
| N1—C6 | 1.4601 (14) | C11—H11 | 0.9300 |
| N1—C7 | 1.3437 (15) | C12—C11 | 1.3703 (18) |
| N2—N1 | 1.3603 (13) | C12—C13 | 1.4199 (16) |
| N2—C13 | 1.3548 (15) | C12—H12 | 0.9300 |
| C1—C6 | 1.5248 (15) | C14—H14A | 0.9700 |
| C1—H1 | 0.9800 | C14—H14B | 0.9700 |
| C2—C1 | 1.4913 (16) | C15—C14 | 1.5149 (15) |
| C2—C3 | 1.3519 (17) | C15—C16 | 1.3942 (16) |
| C3—C4 | 1.4380 (17) | C15—C20 | 1.3981 (16) |
| C3—H3 | 0.9300 | C16—C17 | 1.3980 (16) |
| C4—H4 | 0.9300 | C17—H17 | 0.9300 |
| C5—C4 | 1.3445 (19) | C18—C17 | 1.3841 (18) |
| C5—H5 | 0.9300 | C18—C19 | 1.3901 (18) |
| C6—H6A | 0.9700 | C18—H18 | 0.9300 |
| C6—H6B | 0.9700 | C19—C20 | 1.3861 (16) |
| C7—H7 | 0.9300 | C20—H20 | 0.9300 |
| C8—C7 | 1.3980 (16) | ||
| C14—O1—C1 | 113.25 (8) | C10—C9—H9 | 120.8 |
| C5—O2—C2 | 106.39 (10) | C9—C10—C11 | 121.05 (12) |
| N2—N1—C6 | 119.34 (9) | C9—C10—H10 | 119.5 |
| C7—N1—N2 | 114.58 (10) | C11—C10—H10 | 119.5 |
| C7—N1—C6 | 126.08 (10) | C10—C11—H11 | 119.0 |
| C13—N2—N1 | 103.16 (9) | C12—C11—C10 | 121.96 (11) |
| O1—C1—C2 | 110.75 (9) | C12—C11—H11 | 119.0 |
| O1—C1—C6 | 105.96 (9) | C11—C12—C13 | 117.94 (11) |
| O1—C1—H1 | 109.4 | C11—C12—H12 | 121.0 |
| C2—C1—C6 | 111.85 (9) | C13—C12—H12 | 121.0 |
| C2—C1—H1 | 109.4 | N2—C13—C8 | 111.76 (10) |
| C6—C1—H1 | 109.4 | N2—C13—C12 | 128.06 (11) |
| O2—C2—C1 | 115.82 (10) | C12—C13—C8 | 120.17 (11) |
| C3—C2—O2 | 110.25 (10) | O1—C14—C15 | 110.37 (9) |
| C3—C2—C1 | 133.91 (11) | O1—C14—H14A | 109.6 |
| C2—C3—C4 | 106.19 (11) | O1—C14—H14B | 109.6 |
| C2—C3—H3 | 126.9 | C15—C14—H14A | 109.6 |
| C4—C3—H3 | 126.9 | C15—C14—H14B | 109.6 |
| C3—C4—H4 | 126.7 | H14A—C14—H14B | 108.1 |
| C5—C4—C3 | 106.63 (11) | C16—C15—C14 | 123.97 (10) |
| C5—C4—H4 | 126.7 | C16—C15—C20 | 117.85 (11) |
| O2—C5—H5 | 124.7 | C20—C15—C14 | 118.16 (10) |
| C4—C5—O2 | 110.55 (11) | C15—C16—Cl1 | 120.24 (9) |
| C4—C5—H5 | 124.7 | C15—C16—C17 | 121.87 (11) |
| N1—C6—C1 | 110.63 (9) | C17—C16—Cl1 | 117.87 (9) |
| N1—C6—H6A | 109.5 | C16—C17—H17 | 120.3 |
| N1—C6—H6B | 109.5 | C18—C17—C16 | 119.50 (11) |
| C1—C6—H6A | 109.5 | C18—C17—H17 | 120.3 |
| C1—C6—H6B | 109.5 | C17—C18—C19 | 119.07 (11) |
| H6A—C6—H6B | 108.1 | C17—C18—H18 | 120.5 |
| N1—C7—C8 | 106.25 (10) | C19—C18—H18 | 120.5 |
| N1—C7—H7 | 126.9 | C18—C19—Cl2 | 119.43 (9) |
| C8—C7—H7 | 126.9 | C20—C19—Cl2 | 119.11 (9) |
| C7—C8—C9 | 135.24 (11) | C20—C19—C18 | 121.45 (11) |
| C7—C8—C13 | 104.23 (10) | C15—C20—H20 | 119.9 |
| C9—C8—C13 | 120.48 (11) | C19—C20—C15 | 120.25 (11) |
| C8—C9—H9 | 120.8 | C19—C20—H20 | 119.9 |
| C10—C9—C8 | 118.36 (11) | ||
| C14—O1—C1—C2 | −89.83 (11) | C7—C8—C13—N2 | −1.03 (13) |
| C14—O1—C1—C6 | 148.69 (9) | C7—C8—C13—C12 | −179.97 (10) |
| C1—O1—C14—C15 | −75.87 (11) | C9—C8—C13—N2 | 176.94 (10) |
| C5—O2—C2—C1 | 178.44 (10) | C9—C8—C13—C12 | −2.01 (17) |
| C5—O2—C2—C3 | −0.06 (13) | C10—C9—C8—C7 | 177.63 (13) |
| C2—O2—C5—C4 | −0.05 (14) | C10—C9—C8—C13 | 0.43 (17) |
| N2—N1—C6—C1 | −67.74 (13) | C8—C9—C10—C11 | 1.28 (18) |
| C7—N1—C6—C1 | 112.18 (12) | C9—C10—C11—C12 | −1.5 (2) |
| N2—N1—C7—C8 | −0.85 (13) | C13—C12—C11—C10 | −0.12 (19) |
| C6—N1—C7—C8 | 179.22 (10) | C11—C12—C13—N2 | −176.94 (12) |
| C13—N2—N1—C6 | −179.86 (10) | C11—C12—C13—C8 | 1.81 (17) |
| C13—N2—N1—C7 | 0.21 (13) | C16—C15—C14—O1 | 112.32 (12) |
| N1—N2—C13—C8 | 0.53 (12) | C20—C15—C14—O1 | −65.60 (13) |
| N1—N2—C13—C12 | 179.37 (11) | C14—C15—C16—Cl1 | −0.09 (16) |
| O1—C1—C6—N1 | −69.01 (11) | C14—C15—C16—C17 | −178.88 (11) |
| C2—C1—C6—N1 | 170.22 (9) | C20—C15—C16—Cl1 | 177.83 (9) |
| O2—C2—C1—O1 | −71.29 (12) | C20—C15—C16—C17 | −0.95 (17) |
| O2—C2—C1—C6 | 46.66 (13) | C14—C15—C20—C19 | 179.49 (10) |
| C3—C2—C1—O1 | 106.75 (15) | C16—C15—C20—C19 | 1.44 (17) |
| C3—C2—C1—C6 | −135.30 (14) | Cl1—C16—C17—C18 | −178.91 (9) |
| O2—C2—C3—C4 | 0.13 (14) | C15—C16—C17—C18 | −0.10 (19) |
| C1—C2—C3—C4 | −177.99 (13) | C19—C18—C17—C16 | 0.66 (18) |
| C2—C3—C4—C5 | −0.16 (15) | C17—C18—C19—Cl2 | −179.60 (9) |
| O2—C5—C4—C3 | 0.13 (16) | C17—C18—C19—C20 | −0.16 (18) |
| C9—C8—C7—N1 | −176.43 (13) | Cl2—C19—C20—C15 | 178.52 (9) |
| C13—C8—C7—N1 | 1.08 (12) | C18—C19—C20—C15 | −0.92 (18) |
Hydrogen-bond geometry (Å, º)
Cg4 is the centroid of the N1/N2/C7/C8/C13 ring.
| D—H···A | D—H | H···A | D···A | D—H···A |
| C7—H7···O1i | 0.93 | 2.51 | 3.3062 (15) | 144 |
| C6—H6B···Cg4ii | 0.97 | 2.84 | 3.4583 (13) | 122 |
Symmetry codes: (i) −x+1, −y, −z+2; (ii) −x+2, −y+2, −z.
References
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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, global. DOI: 10.1107/S2056989016013827/xu5891sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989016013827/xu5891Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989016013827/xu5891Isup3.cml
CCDC reference: 1501341
Additional supporting information: crystallographic information; 3D view; checkCIF report