organic compounds
2-[1-(4-tert-Butylphenyl)-4,5-diphenyl-1H-imidazol-2-yl]-4,6-dichlorophenol
aDepartment of Chemistry, Bangalore University, Jnana Bharathi Campus, Bangalore-560 056, Karnataka, India
*Correspondence e-mail: noorsb05@gmail.com
In the title compound, C31H26Cl2N2O, the 4,6-dichlorophenol and the imidazole rings are almost coplanar, with a dihedral angle of 8.89 (6)° between them and an intramolecular O—H⋯N hydrogen bond occurs between the rings. The dihedral angles subtended by the tert-butylphenyl ring and the two phenyl rings with the imidazole ring are 85.18 (9), 81.22 (9) and 19.00 (8)°, respectively. The methyl groups of the tert-butyl grouping are disordered over two sets of sites in 0.589 (5):0.411 (5) ratio. In the crystal, inversion dimers linked by pairs of weak C—H⋯Cl interactions generate R22(24) loops.
Keywords: crystal structure; imidazole derivative; hydrogen bonding.
CCDC reference: 2012170
Structure description
Imidazole is an active part of antifungal compounds like clotrimazole, ketoconazole, miconazole, isoconazole and econazole (Bastide et al., 1982). As part of our studies of imidazole derivatives, we now report the synthesis and of the title compound, which consists of an imidazole ring bearing C10–C15 tert-butylphenyl, C4–C9 4,6-dichlorophenol and C20–C25 and C26–C31 phenyl rings (Fig. 1). The imidazole and the 4,6-dichlorophenol rings are close to coplanar with a dihedral angle of 8.89 (6)°. The dihedral angles between the imidazole ring and the tert-butylphenyl ring and the C20- and C26-phenyl rings are 85.18 (9), 81.22 (9) and 19.00 (8)°, respectively. The C17, C18 and C19 carbon atoms of the tert-butyl group are disordered over two sets of sites in a 0.59:0.41 ratio. A short and presumably strong intramolecular O1—H1⋯N2 hydrogen bond is formed between the O1 atom of the 4,6-dichlorophenol ring and atom N2 of the imidazole ring (Table 1, Fig. 1), forming an S(6) ring, which helps to establish the near coplanarity of the imidazole and phenol rings.
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In the crystal, pairwise C—H⋯Cl interactions involving atoms C29 of the phenyl ring and the Cl2 atom of the phenol group generate centrosymmetric R22(24) loops (Table 1, Fig. 2).
Synthesis and crystallization
The title compound was synthesized by the one-pot reaction of benzil (10 mmol), 4-tert-butylaniline (10 mmol) and 3,5-dichloro-2-hydroxybenzaldehyde (10 mmol) with ammonium acetate (10 mmol) in a glacial acetic acid (20 ml) medium. The mixture was refluxed for 6 h at 343 K, the progress of the reaction being monitored by TLC. After completion of the reaction, the mixture was cooled to room temperature and poured into 100 ml of ice-cold water. The resulting precipitate was filtered, dried and further purified by (7:3 petroleum ether:ethyl acetate) and isolated in good yield (85%). Colourless needles were recrystallized from methanol solution.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 2012170
https://doi.org/10.1107/S2414314620008706/hb4352sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314620008706/hb4352Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314620008706/hb4352Isup3.cml
Data collection: SMART (Bruker, 1998); cell
SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL2018 (Sheldrick, 2015).C31H26Cl2N2O | Z = 2 |
Mr = 513.44 | F(000) = 536 |
Triclinic, P1 | Dx = 1.280 Mg m−3 |
a = 9.8084 (10) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.6806 (11) Å | Cell parameters from 4634 reflections |
c = 12.0754 (13) Å | θ = 3.3–30.8° |
α = 77.474 (6)° | µ = 0.27 mm−1 |
β = 85.686 (6)° | T = 446 K |
γ = 80.742 (6)° | Needle, colorless |
V = 1331.8 (2) Å3 | 0.15 × 0.13 × 0.12 mm |
Bruker SMART APEX CCD diffractometer | 3610 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.037 |
ω scans | θmax = 25.0°, θmin = 3.3° |
Absorption correction: multi-scan (SADABS; Bruker, 1998) | h = −11→11 |
Tmin = 0.862, Tmax = 0.960 | k = −13→13 |
19148 measured reflections | l = −14→14 |
4634 independent reflections |
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)] = 0.063 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.221 | H-atom parameters constrained |
S = 1.14 | w = 1/[σ2(Fo2) + (0.1532P)2 + 0.0304P] where P = (Fo2 + 2Fc2)/3 |
4634 reflections | (Δ/σ)max < 0.001 |
343 parameters | Δρmax = 0.45 e Å−3 |
0 restraints | Δρmin = −0.51 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 | Occ. (<1) | |
Cl1 | 0.68151 (10) | 0.02403 (8) | 0.47335 (7) | 0.0842 (3) | |
Cl2 | 0.83657 (11) | −0.42569 (7) | 0.42892 (8) | 0.0941 (4) | |
N2 | 0.84180 (19) | −0.16232 (18) | 0.01276 (18) | 0.0513 (5) | |
N1 | 0.74765 (18) | 0.02248 (16) | 0.00830 (16) | 0.0443 (5) | |
C10 | 0.6835 (2) | 0.12908 (19) | 0.04413 (18) | 0.0420 (5) | |
O1 | 0.8521 (2) | −0.32598 (16) | 0.19026 (18) | 0.0683 (5) | |
H1 | 0.849884 | −0.296243 | 0.122230 | 0.102* | |
C1 | 0.7867 (2) | −0.0865 (2) | 0.0763 (2) | 0.0475 (5) | |
C4 | 0.7737 (2) | −0.1209 (2) | 0.2000 (2) | 0.0493 (6) | |
C9 | 0.7350 (3) | −0.0408 (2) | 0.2719 (2) | 0.0565 (6) | |
H9 | 0.714640 | 0.039674 | 0.240357 | 0.068* | |
C20 | 0.7522 (2) | 0.1150 (2) | −0.19884 (19) | 0.0457 (5) | |
C3 | 0.7825 (2) | 0.0130 (2) | −0.10358 (19) | 0.0446 (5) | |
C13 | 0.5662 (2) | 0.3168 (2) | 0.1463 (2) | 0.0487 (6) | |
C2 | 0.8415 (2) | −0.1021 (2) | −0.0989 (2) | 0.0472 (5) | |
C11 | 0.5434 (2) | 0.1483 (2) | 0.0672 (2) | 0.0494 (6) | |
H11 | 0.487336 | 0.098558 | 0.048844 | 0.059* | |
C6 | 0.7951 (3) | −0.2766 (2) | 0.3677 (2) | 0.0604 (7) | |
C12 | 0.4858 (2) | 0.2410 (2) | 0.1173 (2) | 0.0535 (6) | |
H12 | 0.390733 | 0.253123 | 0.132195 | 0.064* | |
C26 | 0.9009 (2) | −0.1638 (2) | −0.1902 (2) | 0.0521 (6) | |
C5 | 0.8068 (2) | −0.2424 (2) | 0.2500 (2) | 0.0537 (6) | |
C15 | 0.7649 (2) | 0.2069 (2) | 0.0664 (2) | 0.0518 (6) | |
H15 | 0.859112 | 0.197337 | 0.047397 | 0.062* | |
C7 | 0.7564 (3) | −0.1977 (3) | 0.4363 (2) | 0.0637 (7) | |
H7 | 0.750008 | −0.223624 | 0.514664 | 0.076* | |
C14 | 0.7055 (3) | 0.2987 (2) | 0.1168 (2) | 0.0559 (6) | |
H14 | 0.761210 | 0.350459 | 0.131681 | 0.067* | |
C8 | 0.7265 (3) | −0.0782 (3) | 0.3877 (2) | 0.0608 (7) | |
C23 | 0.7007 (3) | 0.3025 (3) | −0.3821 (2) | 0.0688 (8) | |
H23 | 0.683701 | 0.364908 | −0.444302 | 0.083* | |
C16 | 0.5035 (3) | 0.4127 (3) | 0.2117 (3) | 0.0635 (7) | |
C27 | 0.9426 (3) | −0.1033 (3) | −0.2964 (2) | 0.0655 (7) | |
H27 | 0.930101 | −0.020850 | −0.312384 | 0.079* | |
C31 | 0.9224 (3) | −0.2866 (2) | −0.1699 (3) | 0.0616 (7) | |
H31 | 0.895750 | −0.329589 | −0.099589 | 0.074* | |
C25 | 0.6370 (3) | 0.1268 (3) | −0.2620 (2) | 0.0617 (7) | |
H25 | 0.576498 | 0.071204 | −0.243154 | 0.074* | |
C24 | 0.6116 (3) | 0.2202 (3) | −0.3524 (3) | 0.0708 (8) | |
H24 | 0.533302 | 0.227905 | −0.393903 | 0.085* | |
C21 | 0.8394 (3) | 0.1993 (3) | −0.2284 (3) | 0.0628 (7) | |
H21 | 0.916475 | 0.193590 | −0.185982 | 0.075* | |
C22 | 0.8134 (3) | 0.2921 (3) | −0.3203 (3) | 0.0713 (8) | |
H22 | 0.873597 | 0.347898 | −0.339950 | 0.086* | |
C28 | 1.0019 (3) | −0.1632 (3) | −0.3776 (3) | 0.0777 (9) | |
H28 | 1.029066 | −0.121011 | −0.448159 | 0.093* | |
C29 | 1.0216 (3) | −0.2846 (3) | −0.3563 (3) | 0.0772 (9) | |
H29 | 1.061113 | −0.324753 | −0.412158 | 0.093* | |
C30 | 0.9828 (3) | −0.3463 (3) | −0.2524 (3) | 0.0734 (8) | |
H30 | 0.997088 | −0.428761 | −0.237014 | 0.088* | |
C18 | 0.3485 (11) | 0.4343 (10) | 0.2197 (11) | 0.0954 (19) | 0.411 (5) |
H18A | 0.314639 | 0.361124 | 0.252109 | 0.143* | 0.411 (5) |
H18B | 0.313739 | 0.464925 | 0.145138 | 0.143* | 0.411 (5) |
H18C | 0.318046 | 0.490703 | 0.266842 | 0.143* | 0.411 (5) |
C18' | 0.3761 (8) | 0.4882 (7) | 0.1474 (7) | 0.0954 (19) | 0.589 (5) |
H18D | 0.310146 | 0.437512 | 0.141677 | 0.143* | 0.589 (5) |
H18E | 0.405720 | 0.525813 | 0.072679 | 0.143* | 0.589 (5) |
H18F | 0.334166 | 0.547566 | 0.188362 | 0.143* | 0.589 (5) |
C17 | 0.5525 (19) | 0.3722 (13) | 0.3351 (10) | 0.128 (3) | 0.411 (5) |
H17A | 0.491571 | 0.404759 | 0.390135 | 0.191* | 0.411 (5) |
H17B | 0.628819 | 0.319934 | 0.372610 | 0.191* | 0.411 (5) |
H17C | 0.503172 | 0.328690 | 0.296726 | 0.191* | 0.411 (5) |
C17' | 0.4401 (12) | 0.3491 (9) | 0.3245 (7) | 0.128 (3) | 0.589 (5) |
H17D | 0.394795 | 0.286780 | 0.310901 | 0.191* | 0.589 (5) |
H17E | 0.374022 | 0.404937 | 0.355793 | 0.191* | 0.589 (5) |
H17F | 0.511909 | 0.316061 | 0.377054 | 0.191* | 0.589 (5) |
C19 | 0.6053 (15) | 0.4698 (11) | 0.2511 (13) | 0.113 (3) | 0.411 (5) |
H19A | 0.564836 | 0.507319 | 0.311546 | 0.169* | 0.411 (5) |
H19B | 0.635841 | 0.528419 | 0.189603 | 0.169* | 0.411 (5) |
H19C | 0.682744 | 0.411619 | 0.278258 | 0.169* | 0.411 (5) |
C19' | 0.5770 (10) | 0.5256 (7) | 0.1748 (9) | 0.113 (3) | 0.589 (5) |
H19D | 0.533195 | 0.585609 | 0.214414 | 0.169* | 0.589 (5) |
H19E | 0.570027 | 0.555101 | 0.094509 | 0.169* | 0.589 (5) |
H19F | 0.672616 | 0.505214 | 0.193012 | 0.169* | 0.589 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.1116 (7) | 0.0822 (6) | 0.0570 (5) | −0.0001 (5) | −0.0033 (4) | −0.0208 (4) |
Cl2 | 0.1401 (8) | 0.0527 (5) | 0.0788 (6) | −0.0159 (5) | −0.0115 (5) | 0.0128 (4) |
N2 | 0.0478 (10) | 0.0470 (11) | 0.0576 (12) | 0.0012 (8) | −0.0050 (8) | −0.0125 (9) |
N1 | 0.0457 (9) | 0.0400 (10) | 0.0458 (11) | −0.0017 (7) | −0.0047 (8) | −0.0081 (8) |
C10 | 0.0447 (10) | 0.0393 (11) | 0.0406 (12) | −0.0025 (8) | −0.0061 (8) | −0.0062 (9) |
O1 | 0.0902 (13) | 0.0435 (10) | 0.0673 (12) | −0.0044 (9) | −0.0039 (10) | −0.0069 (9) |
C1 | 0.0452 (11) | 0.0445 (12) | 0.0514 (14) | −0.0033 (9) | −0.0064 (10) | −0.0082 (10) |
C4 | 0.0449 (11) | 0.0477 (13) | 0.0525 (14) | −0.0035 (9) | −0.0074 (10) | −0.0050 (11) |
C9 | 0.0626 (14) | 0.0512 (14) | 0.0508 (14) | 0.0002 (11) | −0.0070 (11) | −0.0049 (11) |
C20 | 0.0438 (11) | 0.0482 (13) | 0.0440 (12) | −0.0029 (9) | 0.0008 (9) | −0.0111 (10) |
C3 | 0.0405 (10) | 0.0480 (13) | 0.0458 (12) | −0.0053 (9) | −0.0034 (9) | −0.0108 (10) |
C13 | 0.0543 (12) | 0.0444 (12) | 0.0454 (13) | −0.0025 (10) | −0.0056 (10) | −0.0073 (10) |
C2 | 0.0422 (11) | 0.0497 (13) | 0.0493 (13) | −0.0021 (9) | −0.0060 (9) | −0.0116 (10) |
C11 | 0.0441 (11) | 0.0456 (13) | 0.0607 (15) | −0.0089 (9) | −0.0047 (10) | −0.0131 (11) |
C6 | 0.0645 (14) | 0.0499 (14) | 0.0615 (16) | −0.0121 (11) | −0.0081 (12) | 0.0040 (12) |
C12 | 0.0410 (11) | 0.0513 (13) | 0.0674 (16) | −0.0028 (10) | −0.0007 (10) | −0.0138 (12) |
C26 | 0.0402 (11) | 0.0576 (14) | 0.0618 (16) | 0.0004 (10) | −0.0085 (10) | −0.0231 (12) |
C5 | 0.0527 (12) | 0.0462 (13) | 0.0610 (16) | −0.0105 (10) | −0.0077 (11) | −0.0043 (11) |
C15 | 0.0405 (11) | 0.0563 (14) | 0.0608 (15) | −0.0080 (10) | −0.0011 (10) | −0.0164 (12) |
C7 | 0.0655 (15) | 0.0681 (18) | 0.0524 (15) | −0.0153 (13) | −0.0084 (12) | 0.0045 (13) |
C14 | 0.0533 (13) | 0.0519 (14) | 0.0674 (16) | −0.0138 (10) | −0.0048 (11) | −0.0182 (12) |
C8 | 0.0591 (14) | 0.0653 (16) | 0.0551 (15) | −0.0051 (12) | −0.0081 (11) | −0.0076 (13) |
C23 | 0.0851 (19) | 0.0612 (17) | 0.0505 (15) | 0.0017 (14) | 0.0043 (14) | −0.0023 (13) |
C16 | 0.0713 (16) | 0.0565 (15) | 0.0638 (17) | −0.0011 (12) | −0.0022 (13) | −0.0215 (13) |
C27 | 0.0728 (16) | 0.0600 (16) | 0.0613 (17) | 0.0010 (13) | 0.0013 (13) | −0.0165 (13) |
C31 | 0.0608 (14) | 0.0574 (15) | 0.0695 (17) | −0.0049 (12) | −0.0015 (12) | −0.0227 (13) |
C25 | 0.0581 (14) | 0.0676 (17) | 0.0586 (16) | −0.0150 (12) | −0.0105 (12) | −0.0049 (13) |
C24 | 0.0754 (17) | 0.0769 (19) | 0.0556 (16) | −0.0049 (15) | −0.0203 (13) | −0.0031 (14) |
C21 | 0.0549 (13) | 0.0623 (16) | 0.0690 (18) | −0.0136 (12) | −0.0048 (12) | −0.0048 (13) |
C22 | 0.0755 (18) | 0.0624 (18) | 0.0722 (19) | −0.0179 (14) | 0.0091 (15) | −0.0042 (15) |
C28 | 0.0844 (19) | 0.088 (2) | 0.0586 (18) | −0.0001 (17) | 0.0062 (15) | −0.0238 (16) |
C29 | 0.0728 (17) | 0.089 (2) | 0.074 (2) | 0.0046 (16) | 0.0006 (15) | −0.0403 (18) |
C30 | 0.0730 (17) | 0.0613 (17) | 0.091 (2) | 0.0015 (14) | −0.0071 (15) | −0.0337 (17) |
C18 | 0.104 (4) | 0.077 (4) | 0.101 (5) | 0.029 (3) | −0.009 (4) | −0.040 (3) |
C18' | 0.104 (4) | 0.077 (4) | 0.101 (5) | 0.029 (3) | −0.009 (4) | −0.040 (3) |
C17 | 0.195 (9) | 0.114 (5) | 0.058 (3) | 0.024 (7) | 0.023 (6) | −0.029 (3) |
C17' | 0.195 (9) | 0.114 (5) | 0.058 (3) | 0.024 (7) | 0.023 (6) | −0.029 (3) |
C19 | 0.154 (6) | 0.066 (4) | 0.132 (7) | −0.031 (5) | 0.038 (6) | −0.058 (4) |
C19' | 0.154 (6) | 0.066 (4) | 0.132 (7) | −0.031 (5) | 0.038 (6) | −0.058 (4) |
Cl1—C8 | 1.729 (3) | C16—C18 | 1.500 (11) |
Cl2—C6 | 1.733 (3) | C16—C17' | 1.542 (9) |
N2—C1 | 1.321 (3) | C16—C17 | 1.550 (14) |
N2—C2 | 1.379 (3) | C16—C18' | 1.561 (8) |
N1—C1 | 1.370 (3) | C16—C19' | 1.567 (8) |
N1—C3 | 1.392 (3) | C27—C28 | 1.368 (4) |
N1—C10 | 1.440 (3) | C27—H27 | 0.9300 |
C10—C11 | 1.374 (3) | C31—C30 | 1.381 (4) |
C10—C15 | 1.382 (3) | C31—H31 | 0.9300 |
O1—C5 | 1.338 (3) | C25—C24 | 1.371 (4) |
O1—H1 | 0.8200 | C25—H25 | 0.9300 |
C1—C4 | 1.461 (3) | C24—H24 | 0.9300 |
C4—C9 | 1.400 (4) | C21—C22 | 1.380 (4) |
C4—C5 | 1.412 (3) | C21—H21 | 0.9300 |
C9—C8 | 1.372 (4) | C22—H22 | 0.9300 |
C9—H9 | 0.9300 | C28—C29 | 1.370 (5) |
C20—C21 | 1.380 (3) | C28—H28 | 0.9300 |
C20—C25 | 1.383 (4) | C29—C30 | 1.365 (5) |
C20—C3 | 1.474 (3) | C29—H29 | 0.9300 |
C3—C2 | 1.367 (3) | C30—H30 | 0.9300 |
C13—C14 | 1.380 (3) | C18—H18A | 0.9600 |
C13—C12 | 1.389 (3) | C18—H18B | 0.9600 |
C13—C16 | 1.532 (3) | C18—H18C | 0.9600 |
C2—C26 | 1.479 (3) | C18'—H18D | 0.9600 |
C11—C12 | 1.376 (3) | C18'—H18E | 0.9600 |
C11—H11 | 0.9300 | C18'—H18F | 0.9600 |
C6—C7 | 1.360 (4) | C17—C19 | 1.49 (2) |
C6—C5 | 1.392 (4) | C17—H17A | 0.9600 |
C12—H12 | 0.9300 | C17—H17B | 0.9600 |
C26—C31 | 1.386 (4) | C17—H17C | 0.9600 |
C26—C27 | 1.390 (4) | C17'—H17D | 0.9600 |
C15—C14 | 1.374 (4) | C17'—H17E | 0.9600 |
C15—H15 | 0.9300 | C17'—H17F | 0.9600 |
C7—C8 | 1.384 (4) | C19—H19A | 0.9600 |
C7—H7 | 0.9300 | C19—H19B | 0.9600 |
C14—H14 | 0.9300 | C19—H19C | 0.9600 |
C23—C22 | 1.355 (5) | C19'—H19D | 0.9600 |
C23—C24 | 1.376 (4) | C19'—H19E | 0.9600 |
C23—H23 | 0.9300 | C19'—H19F | 0.9600 |
C16—C19 | 1.445 (14) | ||
C1—N2—C2 | 107.9 (2) | C28—C27—C26 | 121.0 (3) |
C1—N1—C3 | 107.68 (19) | C28—C27—H27 | 119.5 |
C1—N1—C10 | 127.05 (19) | C26—C27—H27 | 119.5 |
C3—N1—C10 | 125.27 (18) | C30—C31—C26 | 121.1 (3) |
C11—C10—C15 | 119.5 (2) | C30—C31—H31 | 119.5 |
C11—C10—N1 | 120.52 (19) | C26—C31—H31 | 119.5 |
C15—C10—N1 | 119.68 (18) | C24—C25—C20 | 120.2 (3) |
C5—O1—H1 | 109.5 | C24—C25—H25 | 119.9 |
N2—C1—N1 | 109.5 (2) | C20—C25—H25 | 119.9 |
N2—C1—C4 | 122.1 (2) | C25—C24—C23 | 120.6 (3) |
N1—C1—C4 | 128.3 (2) | C25—C24—H24 | 119.7 |
C9—C4—C5 | 118.1 (2) | C23—C24—H24 | 119.7 |
C9—C4—C1 | 124.2 (2) | C20—C21—C22 | 120.6 (3) |
C5—C4—C1 | 117.7 (2) | C20—C21—H21 | 119.7 |
C8—C9—C4 | 121.6 (3) | C22—C21—H21 | 119.7 |
C8—C9—H9 | 119.2 | C23—C22—C21 | 120.4 (3) |
C4—C9—H9 | 119.2 | C23—C22—H22 | 119.8 |
C21—C20—C25 | 118.5 (2) | C21—C22—H22 | 119.8 |
C21—C20—C3 | 120.8 (2) | C27—C28—C29 | 120.7 (3) |
C25—C20—C3 | 120.6 (2) | C27—C28—H28 | 119.7 |
C2—C3—N1 | 105.9 (2) | C29—C28—H28 | 119.7 |
C2—C3—C20 | 132.6 (2) | C30—C29—C28 | 119.5 (3) |
N1—C3—C20 | 121.47 (19) | C30—C29—H29 | 120.2 |
C14—C13—C12 | 116.8 (2) | C28—C29—H29 | 120.2 |
C14—C13—C16 | 121.8 (2) | C29—C30—C31 | 120.2 (3) |
C12—C13—C16 | 121.3 (2) | C29—C30—H30 | 119.9 |
C3—C2—N2 | 109.0 (2) | C31—C30—H30 | 119.9 |
C3—C2—C26 | 130.7 (2) | C16—C18—H18A | 109.5 |
N2—C2—C26 | 120.2 (2) | C16—C18—H18B | 109.5 |
C10—C11—C12 | 120.1 (2) | H18A—C18—H18B | 109.5 |
C10—C11—H11 | 120.0 | C16—C18—H18C | 109.5 |
C12—C11—H11 | 120.0 | H18A—C18—H18C | 109.5 |
C7—C6—C5 | 122.7 (2) | H18B—C18—H18C | 109.5 |
C7—C6—Cl2 | 119.0 (2) | C16—C18'—H18D | 109.5 |
C5—C6—Cl2 | 118.3 (2) | C16—C18'—H18E | 109.5 |
C11—C12—C13 | 121.6 (2) | H18D—C18'—H18E | 109.5 |
C11—C12—H12 | 119.2 | C16—C18'—H18F | 109.5 |
C13—C12—H12 | 119.2 | H18D—C18'—H18F | 109.5 |
C31—C26—C27 | 117.5 (2) | H18E—C18'—H18F | 109.5 |
C31—C26—C2 | 120.1 (2) | C19—C17—C16 | 56.8 (8) |
C27—C26—C2 | 122.4 (2) | C19—C17—H17A | 109.5 |
O1—C5—C6 | 118.3 (2) | C16—C17—H17A | 114.2 |
O1—C5—C4 | 123.3 (2) | C19—C17—H17B | 109.5 |
C6—C5—C4 | 118.4 (2) | C16—C17—H17B | 136.3 |
C14—C15—C10 | 119.4 (2) | H17A—C17—H17B | 109.5 |
C14—C15—H15 | 120.3 | C19—C17—H17C | 109.5 |
C10—C15—H15 | 120.3 | C16—C17—H17C | 54.2 |
C6—C7—C8 | 119.1 (3) | H17A—C17—H17C | 109.5 |
C6—C7—H7 | 120.5 | H17B—C17—H17C | 109.5 |
C8—C7—H7 | 120.5 | C16—C17'—H17D | 109.5 |
C15—C14—C13 | 122.4 (2) | C16—C17'—H17E | 109.5 |
C15—C14—H14 | 118.8 | H17D—C17'—H17E | 109.5 |
C13—C14—H14 | 118.8 | C16—C17'—H17F | 109.5 |
C9—C8—C7 | 120.1 (3) | H17D—C17'—H17F | 109.5 |
C9—C8—Cl1 | 120.1 (2) | H17E—C17'—H17F | 109.5 |
C7—C8—Cl1 | 119.9 (2) | C16—C19—C17 | 63.9 (8) |
C22—C23—C24 | 119.6 (3) | C16—C19—H19A | 109.5 |
C22—C23—H23 | 120.2 | C17—C19—H19A | 76.2 |
C24—C23—H23 | 120.2 | C16—C19—H19B | 109.5 |
C19—C16—C18 | 131.4 (6) | C17—C19—H19B | 172.8 |
C19—C16—C13 | 113.7 (5) | H19A—C19—H19B | 109.5 |
C18—C16—C13 | 114.8 (4) | C16—C19—H19C | 109.5 |
C13—C16—C17' | 107.0 (4) | C17—C19—H19C | 71.7 |
C19—C16—C17 | 59.3 (9) | H19A—C19—H19C | 109.5 |
C18—C16—C17 | 106.7 (8) | H19B—C19—H19C | 109.5 |
C13—C16—C17 | 107.8 (5) | C16—C19'—H19D | 109.5 |
C13—C16—C18' | 108.4 (3) | C16—C19'—H19E | 109.5 |
C17'—C16—C18' | 103.9 (5) | H19D—C19'—H19E | 109.5 |
C13—C16—C19' | 111.1 (3) | C16—C19'—H19F | 109.5 |
C17'—C16—C19' | 134.6 (6) | H19D—C19'—H19F | 109.5 |
C18'—C16—C19' | 86.8 (6) | H19E—C19'—H19F | 109.5 |
C1—N1—C10—C11 | −82.3 (3) | C9—C4—C5—C6 | 2.0 (3) |
C3—N1—C10—C11 | 98.5 (3) | C1—C4—C5—C6 | 179.9 (2) |
C1—N1—C10—C15 | 91.3 (3) | C11—C10—C15—C14 | 3.5 (4) |
C3—N1—C10—C15 | −88.0 (3) | N1—C10—C15—C14 | −170.1 (2) |
C2—N2—C1—N1 | 1.1 (2) | C5—C6—C7—C8 | 0.3 (4) |
C2—N2—C1—C4 | −178.75 (19) | Cl2—C6—C7—C8 | 178.4 (2) |
C3—N1—C1—N2 | −0.7 (2) | C10—C15—C14—C13 | −0.2 (4) |
C10—N1—C1—N2 | 179.92 (19) | C12—C13—C14—C15 | −3.2 (4) |
C3—N1—C1—C4 | 179.1 (2) | C16—C13—C14—C15 | 174.6 (2) |
C10—N1—C1—C4 | −0.3 (3) | C4—C9—C8—C7 | −0.1 (4) |
N2—C1—C4—C9 | 170.3 (2) | C4—C9—C8—Cl1 | 178.79 (19) |
N1—C1—C4—C9 | −9.5 (4) | C6—C7—C8—C9 | 0.6 (4) |
N2—C1—C4—C5 | −7.5 (3) | C6—C7—C8—Cl1 | −178.3 (2) |
N1—C1—C4—C5 | 172.7 (2) | C14—C13—C16—C19 | −7.5 (8) |
C5—C4—C9—C8 | −1.2 (4) | C12—C13—C16—C19 | 170.1 (7) |
C1—C4—C9—C8 | −179.0 (2) | C14—C13—C16—C18 | 170.2 (6) |
C1—N1—C3—C2 | 0.1 (2) | C12—C13—C16—C18 | −12.2 (7) |
C10—N1—C3—C2 | 179.45 (18) | C14—C13—C16—C17' | −119.1 (5) |
C1—N1—C3—C20 | 179.06 (18) | C12—C13—C16—C17' | 58.6 (6) |
C10—N1—C3—C20 | −1.6 (3) | C14—C13—C16—C17 | −71.2 (8) |
C21—C20—C3—C2 | −98.9 (3) | C12—C13—C16—C17 | 106.5 (7) |
C25—C20—C3—C2 | 79.8 (3) | C14—C13—C16—C18' | 129.4 (4) |
C21—C20—C3—N1 | 82.4 (3) | C12—C13—C16—C18' | −52.9 (5) |
C25—C20—C3—N1 | −98.9 (3) | C14—C13—C16—C19' | 35.7 (6) |
N1—C3—C2—N2 | 0.6 (2) | C12—C13—C16—C19' | −146.6 (5) |
C20—C3—C2—N2 | −178.3 (2) | C31—C26—C27—C28 | 0.4 (4) |
N1—C3—C2—C26 | −178.7 (2) | C2—C26—C27—C28 | 177.6 (2) |
C20—C3—C2—C26 | 2.5 (4) | C27—C26—C31—C30 | −0.1 (4) |
C1—N2—C2—C3 | −1.0 (2) | C2—C26—C31—C30 | −177.4 (2) |
C1—N2—C2—C26 | 178.30 (19) | C21—C20—C25—C24 | 0.5 (4) |
C15—C10—C11—C12 | −3.3 (4) | C3—C20—C25—C24 | −178.3 (3) |
N1—C10—C11—C12 | 170.3 (2) | C20—C25—C24—C23 | 0.7 (5) |
C10—C11—C12—C13 | −0.2 (4) | C22—C23—C24—C25 | −1.1 (5) |
C14—C13—C12—C11 | 3.4 (4) | C25—C20—C21—C22 | −1.2 (4) |
C16—C13—C12—C11 | −174.4 (2) | C3—C20—C21—C22 | 177.5 (2) |
C3—C2—C26—C31 | −163.2 (2) | C24—C23—C22—C21 | 0.4 (5) |
N2—C2—C26—C31 | 17.6 (3) | C20—C21—C22—C23 | 0.8 (5) |
C3—C2—C26—C27 | 19.6 (4) | C26—C27—C28—C29 | 0.0 (5) |
N2—C2—C26—C27 | −159.5 (2) | C27—C28—C29—C30 | −0.6 (5) |
C7—C6—C5—O1 | 176.8 (2) | C28—C29—C30—C31 | 0.9 (5) |
Cl2—C6—C5—O1 | −1.3 (3) | C26—C31—C30—C29 | −0.5 (4) |
C7—C6—C5—C4 | −1.6 (4) | C18—C16—C17—C19 | −128.7 (8) |
Cl2—C6—C5—C4 | −179.73 (18) | C13—C16—C17—C19 | 107.5 (6) |
C9—C4—C5—O1 | −176.3 (2) | C18—C16—C19—C17 | 85.5 (11) |
C1—C4—C5—O1 | 1.6 (3) | C13—C16—C19—C17 | −97.3 (7) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N2 | 0.82 | 1.81 | 2.541 (2) | 147 |
C29—H29···Cl2i | 0.93 | 2.97 | 3.705 (3) | 137 |
Symmetry code: (i) −x+2, −y−1, −z. |
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