organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoIUCrDATA
ISSN: 2414-3146

2-[1-(4-tert-Butyl­phen­yl)-4,5-di­phenyl-1H-imid­azol-2-yl]-4,6-di­chloro­phenol

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aDepartment of Chemistry, Bangalore University, Jnana Bharathi Campus, Bangalore-560 056, Karnataka, India
*Correspondence e-mail: noorsb05@gmail.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 26 June 2020; accepted 27 June 2020; online 21 July 2020)

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.

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

Imidazole is an active part of anti­fungal compounds like clotrimazole, ketoconazole, miconazole, isoconazole and econazole (Bastide et al., 1982[Bastide, M., Jouvert, S. & Bastide, J. M. (1982). Can. J. Microbiol. 28, 1119-1126.]). As part of our studies of imidazole derivatives, we now report the synthesis and crystal structure 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[link]). 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[link], Fig. 1[link]), forming an S(6) ring, which helps to establish the near coplanarity of the imidazole and phenol rings.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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.
[Figure 1]
Figure 1
The mol­ecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level. The hydrogen bond is indicated by a double-dashed line.

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[link], Fig. 2[link]).

[Figure 2]
Figure 2
Unit-cell packing of the title compound showing intra­molecular O—H⋯N and inter­molecular C—H⋯Cl inter­actions with dotted lines. H atoms not involved in hydrogen bonding have been excluded.

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 column chromatography (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 refinement details are summarized in Table 2[link].

Table 2
Experimental details

Crystal data
Chemical formula C31H26Cl2N2O
Mr 513.44
Crystal system, space group Triclinic, P[\overline{1}]
Temperature (K) 446
a, b, c (Å) 9.8084 (10), 11.6806 (11), 12.0754 (13)
α, β, γ (°) 77.474 (6), 85.686 (6), 80.742 (6)
V3) 1331.8 (2)
Z 2
Radiation type Mo Kα
μ (mm−1) 0.27
Crystal size (mm) 0.15 × 0.13 × 0.12
 
Data collection
Diffractometer Bruker SMART APEX CCD
Absorption correction Multi-scan (SADABS; Bruker, 1998[Bruker. (1998). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.862, 0.960
No. of measured, independent and observed [I > 2σ(I)] reflections 19148, 4634, 3610
Rint 0.037
(sin θ/λ)max−1) 0.595
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.063, 0.221, 1.14
No. of reflections 4634
No. of parameters 343
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.45, −0.51
Computer programs: SMART and SAINT-Plus (Bruker, 1998[Bruker. (1998). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), SHELXL2018 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]) and ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).

Structural data


Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: 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).

2-[1-(4-tert-Butylphenyl)-4,5-diphenyl-1H-imidazol-2-yl]-4,6-dichlorophenol top
Crystal data top
C31H26Cl2N2OZ = 2
Mr = 513.44F(000) = 536
Triclinic, P1Dx = 1.280 Mg m3
a = 9.8084 (10) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.6806 (11) ÅCell parameters from 4634 reflections
c = 12.0754 (13) Åθ = 3.3–30.8°
α = 77.474 (6)°µ = 0.27 mm1
β = 85.686 (6)°T = 446 K
γ = 80.742 (6)°Needle, colorless
V = 1331.8 (2) Å30.15 × 0.13 × 0.12 mm
Data collection top
Bruker SMART APEX CCD
diffractometer
3610 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.037
ω scansθmax = 25.0°, θmin = 3.3°
Absorption correction: multi-scan
(SADABS; Bruker, 1998)
h = 1111
Tmin = 0.862, Tmax = 0.960k = 1313
19148 measured reflectionsl = 1414
4634 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.063Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.221H-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 parametersΔρmax = 0.45 e Å3
0 restraintsΔρmin = 0.51 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cl10.68151 (10)0.02403 (8)0.47335 (7)0.0842 (3)
Cl20.83657 (11)0.42569 (7)0.42892 (8)0.0941 (4)
N20.84180 (19)0.16232 (18)0.01276 (18)0.0513 (5)
N10.74765 (18)0.02248 (16)0.00830 (16)0.0443 (5)
C100.6835 (2)0.12908 (19)0.04413 (18)0.0420 (5)
O10.8521 (2)0.32598 (16)0.19026 (18)0.0683 (5)
H10.8498840.2962430.1222300.102*
C10.7867 (2)0.0865 (2)0.0763 (2)0.0475 (5)
C40.7737 (2)0.1209 (2)0.2000 (2)0.0493 (6)
C90.7350 (3)0.0408 (2)0.2719 (2)0.0565 (6)
H90.7146400.0396740.2403570.068*
C200.7522 (2)0.1150 (2)0.19884 (19)0.0457 (5)
C30.7825 (2)0.0130 (2)0.10358 (19)0.0446 (5)
C130.5662 (2)0.3168 (2)0.1463 (2)0.0487 (6)
C20.8415 (2)0.1021 (2)0.0989 (2)0.0472 (5)
C110.5434 (2)0.1483 (2)0.0672 (2)0.0494 (6)
H110.4873360.0985580.0488440.059*
C60.7951 (3)0.2766 (2)0.3677 (2)0.0604 (7)
C120.4858 (2)0.2410 (2)0.1173 (2)0.0535 (6)
H120.3907330.2531230.1321950.064*
C260.9009 (2)0.1638 (2)0.1902 (2)0.0521 (6)
C50.8068 (2)0.2424 (2)0.2500 (2)0.0537 (6)
C150.7649 (2)0.2069 (2)0.0664 (2)0.0518 (6)
H150.8591120.1973370.0473970.062*
C70.7564 (3)0.1977 (3)0.4363 (2)0.0637 (7)
H70.7500080.2236240.5146640.076*
C140.7055 (3)0.2987 (2)0.1168 (2)0.0559 (6)
H140.7612100.3504590.1316810.067*
C80.7265 (3)0.0782 (3)0.3877 (2)0.0608 (7)
C230.7007 (3)0.3025 (3)0.3821 (2)0.0688 (8)
H230.6837010.3649080.4443020.083*
C160.5035 (3)0.4127 (3)0.2117 (3)0.0635 (7)
C270.9426 (3)0.1033 (3)0.2964 (2)0.0655 (7)
H270.9301010.0208500.3123840.079*
C310.9224 (3)0.2866 (2)0.1699 (3)0.0616 (7)
H310.8957500.3295890.0995890.074*
C250.6370 (3)0.1268 (3)0.2620 (2)0.0617 (7)
H250.5764980.0712040.2431540.074*
C240.6116 (3)0.2202 (3)0.3524 (3)0.0708 (8)
H240.5333020.2279050.3939030.085*
C210.8394 (3)0.1993 (3)0.2284 (3)0.0628 (7)
H210.9164750.1935900.1859820.075*
C220.8134 (3)0.2921 (3)0.3203 (3)0.0713 (8)
H220.8735970.3478980.3399500.086*
C281.0019 (3)0.1632 (3)0.3776 (3)0.0777 (9)
H281.0290660.1210110.4481590.093*
C291.0216 (3)0.2846 (3)0.3563 (3)0.0772 (9)
H291.0611130.3247530.4121580.093*
C300.9828 (3)0.3463 (3)0.2524 (3)0.0734 (8)
H300.9970880.4287610.2370140.088*
C180.3485 (11)0.4343 (10)0.2197 (11)0.0954 (19)0.411 (5)
H18A0.3146390.3611240.2521090.143*0.411 (5)
H18B0.3137390.4649250.1451380.143*0.411 (5)
H18C0.3180460.4907030.2668420.143*0.411 (5)
C18'0.3761 (8)0.4882 (7)0.1474 (7)0.0954 (19)0.589 (5)
H18D0.3101460.4375120.1416770.143*0.589 (5)
H18E0.4057200.5258130.0726790.143*0.589 (5)
H18F0.3341660.5475660.1883620.143*0.589 (5)
C170.5525 (19)0.3722 (13)0.3351 (10)0.128 (3)0.411 (5)
H17A0.4915710.4047590.3901350.191*0.411 (5)
H17B0.6288190.3199340.3726100.191*0.411 (5)
H17C0.5031720.3286900.2967260.191*0.411 (5)
C17'0.4401 (12)0.3491 (9)0.3245 (7)0.128 (3)0.589 (5)
H17D0.3947950.2867800.3109010.191*0.589 (5)
H17E0.3740220.4049370.3557930.191*0.589 (5)
H17F0.5119090.3160610.3770540.191*0.589 (5)
C190.6053 (15)0.4698 (11)0.2511 (13)0.113 (3)0.411 (5)
H19A0.5648360.5073190.3115460.169*0.411 (5)
H19B0.6358410.5284190.1896030.169*0.411 (5)
H19C0.6827440.4116190.2782580.169*0.411 (5)
C19'0.5770 (10)0.5256 (7)0.1748 (9)0.113 (3)0.589 (5)
H19D0.5331950.5856090.2144140.169*0.589 (5)
H19E0.5700270.5551010.0945090.169*0.589 (5)
H19F0.6726160.5052140.1930120.169*0.589 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.1116 (7)0.0822 (6)0.0570 (5)0.0001 (5)0.0033 (4)0.0208 (4)
Cl20.1401 (8)0.0527 (5)0.0788 (6)0.0159 (5)0.0115 (5)0.0128 (4)
N20.0478 (10)0.0470 (11)0.0576 (12)0.0012 (8)0.0050 (8)0.0125 (9)
N10.0457 (9)0.0400 (10)0.0458 (11)0.0017 (7)0.0047 (8)0.0081 (8)
C100.0447 (10)0.0393 (11)0.0406 (12)0.0025 (8)0.0061 (8)0.0062 (9)
O10.0902 (13)0.0435 (10)0.0673 (12)0.0044 (9)0.0039 (10)0.0069 (9)
C10.0452 (11)0.0445 (12)0.0514 (14)0.0033 (9)0.0064 (10)0.0082 (10)
C40.0449 (11)0.0477 (13)0.0525 (14)0.0035 (9)0.0074 (10)0.0050 (11)
C90.0626 (14)0.0512 (14)0.0508 (14)0.0002 (11)0.0070 (11)0.0049 (11)
C200.0438 (11)0.0482 (13)0.0440 (12)0.0029 (9)0.0008 (9)0.0111 (10)
C30.0405 (10)0.0480 (13)0.0458 (12)0.0053 (9)0.0034 (9)0.0108 (10)
C130.0543 (12)0.0444 (12)0.0454 (13)0.0025 (10)0.0056 (10)0.0073 (10)
C20.0422 (11)0.0497 (13)0.0493 (13)0.0021 (9)0.0060 (9)0.0116 (10)
C110.0441 (11)0.0456 (13)0.0607 (15)0.0089 (9)0.0047 (10)0.0131 (11)
C60.0645 (14)0.0499 (14)0.0615 (16)0.0121 (11)0.0081 (12)0.0040 (12)
C120.0410 (11)0.0513 (13)0.0674 (16)0.0028 (10)0.0007 (10)0.0138 (12)
C260.0402 (11)0.0576 (14)0.0618 (16)0.0004 (10)0.0085 (10)0.0231 (12)
C50.0527 (12)0.0462 (13)0.0610 (16)0.0105 (10)0.0077 (11)0.0043 (11)
C150.0405 (11)0.0563 (14)0.0608 (15)0.0080 (10)0.0011 (10)0.0164 (12)
C70.0655 (15)0.0681 (18)0.0524 (15)0.0153 (13)0.0084 (12)0.0045 (13)
C140.0533 (13)0.0519 (14)0.0674 (16)0.0138 (10)0.0048 (11)0.0182 (12)
C80.0591 (14)0.0653 (16)0.0551 (15)0.0051 (12)0.0081 (11)0.0076 (13)
C230.0851 (19)0.0612 (17)0.0505 (15)0.0017 (14)0.0043 (14)0.0023 (13)
C160.0713 (16)0.0565 (15)0.0638 (17)0.0011 (12)0.0022 (13)0.0215 (13)
C270.0728 (16)0.0600 (16)0.0613 (17)0.0010 (13)0.0013 (13)0.0165 (13)
C310.0608 (14)0.0574 (15)0.0695 (17)0.0049 (12)0.0015 (12)0.0227 (13)
C250.0581 (14)0.0676 (17)0.0586 (16)0.0150 (12)0.0105 (12)0.0049 (13)
C240.0754 (17)0.0769 (19)0.0556 (16)0.0049 (15)0.0203 (13)0.0031 (14)
C210.0549 (13)0.0623 (16)0.0690 (18)0.0136 (12)0.0048 (12)0.0048 (13)
C220.0755 (18)0.0624 (18)0.0722 (19)0.0179 (14)0.0091 (15)0.0042 (15)
C280.0844 (19)0.088 (2)0.0586 (18)0.0001 (17)0.0062 (15)0.0238 (16)
C290.0728 (17)0.089 (2)0.074 (2)0.0046 (16)0.0006 (15)0.0403 (18)
C300.0730 (17)0.0613 (17)0.091 (2)0.0015 (14)0.0071 (15)0.0337 (17)
C180.104 (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)
C170.195 (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)
C190.154 (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)
Geometric parameters (Å, º) top
Cl1—C81.729 (3)C16—C181.500 (11)
Cl2—C61.733 (3)C16—C17'1.542 (9)
N2—C11.321 (3)C16—C171.550 (14)
N2—C21.379 (3)C16—C18'1.561 (8)
N1—C11.370 (3)C16—C19'1.567 (8)
N1—C31.392 (3)C27—C281.368 (4)
N1—C101.440 (3)C27—H270.9300
C10—C111.374 (3)C31—C301.381 (4)
C10—C151.382 (3)C31—H310.9300
O1—C51.338 (3)C25—C241.371 (4)
O1—H10.8200C25—H250.9300
C1—C41.461 (3)C24—H240.9300
C4—C91.400 (4)C21—C221.380 (4)
C4—C51.412 (3)C21—H210.9300
C9—C81.372 (4)C22—H220.9300
C9—H90.9300C28—C291.370 (5)
C20—C211.380 (3)C28—H280.9300
C20—C251.383 (4)C29—C301.365 (5)
C20—C31.474 (3)C29—H290.9300
C3—C21.367 (3)C30—H300.9300
C13—C141.380 (3)C18—H18A0.9600
C13—C121.389 (3)C18—H18B0.9600
C13—C161.532 (3)C18—H18C0.9600
C2—C261.479 (3)C18'—H18D0.9600
C11—C121.376 (3)C18'—H18E0.9600
C11—H110.9300C18'—H18F0.9600
C6—C71.360 (4)C17—C191.49 (2)
C6—C51.392 (4)C17—H17A0.9600
C12—H120.9300C17—H17B0.9600
C26—C311.386 (4)C17—H17C0.9600
C26—C271.390 (4)C17'—H17D0.9600
C15—C141.374 (4)C17'—H17E0.9600
C15—H150.9300C17'—H17F0.9600
C7—C81.384 (4)C19—H19A0.9600
C7—H70.9300C19—H19B0.9600
C14—H140.9300C19—H19C0.9600
C23—C221.355 (5)C19'—H19D0.9600
C23—C241.376 (4)C19'—H19E0.9600
C23—H230.9300C19'—H19F0.9600
C16—C191.445 (14)
C1—N2—C2107.9 (2)C28—C27—C26121.0 (3)
C1—N1—C3107.68 (19)C28—C27—H27119.5
C1—N1—C10127.05 (19)C26—C27—H27119.5
C3—N1—C10125.27 (18)C30—C31—C26121.1 (3)
C11—C10—C15119.5 (2)C30—C31—H31119.5
C11—C10—N1120.52 (19)C26—C31—H31119.5
C15—C10—N1119.68 (18)C24—C25—C20120.2 (3)
C5—O1—H1109.5C24—C25—H25119.9
N2—C1—N1109.5 (2)C20—C25—H25119.9
N2—C1—C4122.1 (2)C25—C24—C23120.6 (3)
N1—C1—C4128.3 (2)C25—C24—H24119.7
C9—C4—C5118.1 (2)C23—C24—H24119.7
C9—C4—C1124.2 (2)C20—C21—C22120.6 (3)
C5—C4—C1117.7 (2)C20—C21—H21119.7
C8—C9—C4121.6 (3)C22—C21—H21119.7
C8—C9—H9119.2C23—C22—C21120.4 (3)
C4—C9—H9119.2C23—C22—H22119.8
C21—C20—C25118.5 (2)C21—C22—H22119.8
C21—C20—C3120.8 (2)C27—C28—C29120.7 (3)
C25—C20—C3120.6 (2)C27—C28—H28119.7
C2—C3—N1105.9 (2)C29—C28—H28119.7
C2—C3—C20132.6 (2)C30—C29—C28119.5 (3)
N1—C3—C20121.47 (19)C30—C29—H29120.2
C14—C13—C12116.8 (2)C28—C29—H29120.2
C14—C13—C16121.8 (2)C29—C30—C31120.2 (3)
C12—C13—C16121.3 (2)C29—C30—H30119.9
C3—C2—N2109.0 (2)C31—C30—H30119.9
C3—C2—C26130.7 (2)C16—C18—H18A109.5
N2—C2—C26120.2 (2)C16—C18—H18B109.5
C10—C11—C12120.1 (2)H18A—C18—H18B109.5
C10—C11—H11120.0C16—C18—H18C109.5
C12—C11—H11120.0H18A—C18—H18C109.5
C7—C6—C5122.7 (2)H18B—C18—H18C109.5
C7—C6—Cl2119.0 (2)C16—C18'—H18D109.5
C5—C6—Cl2118.3 (2)C16—C18'—H18E109.5
C11—C12—C13121.6 (2)H18D—C18'—H18E109.5
C11—C12—H12119.2C16—C18'—H18F109.5
C13—C12—H12119.2H18D—C18'—H18F109.5
C31—C26—C27117.5 (2)H18E—C18'—H18F109.5
C31—C26—C2120.1 (2)C19—C17—C1656.8 (8)
C27—C26—C2122.4 (2)C19—C17—H17A109.5
O1—C5—C6118.3 (2)C16—C17—H17A114.2
O1—C5—C4123.3 (2)C19—C17—H17B109.5
C6—C5—C4118.4 (2)C16—C17—H17B136.3
C14—C15—C10119.4 (2)H17A—C17—H17B109.5
C14—C15—H15120.3C19—C17—H17C109.5
C10—C15—H15120.3C16—C17—H17C54.2
C6—C7—C8119.1 (3)H17A—C17—H17C109.5
C6—C7—H7120.5H17B—C17—H17C109.5
C8—C7—H7120.5C16—C17'—H17D109.5
C15—C14—C13122.4 (2)C16—C17'—H17E109.5
C15—C14—H14118.8H17D—C17'—H17E109.5
C13—C14—H14118.8C16—C17'—H17F109.5
C9—C8—C7120.1 (3)H17D—C17'—H17F109.5
C9—C8—Cl1120.1 (2)H17E—C17'—H17F109.5
C7—C8—Cl1119.9 (2)C16—C19—C1763.9 (8)
C22—C23—C24119.6 (3)C16—C19—H19A109.5
C22—C23—H23120.2C17—C19—H19A76.2
C24—C23—H23120.2C16—C19—H19B109.5
C19—C16—C18131.4 (6)C17—C19—H19B172.8
C19—C16—C13113.7 (5)H19A—C19—H19B109.5
C18—C16—C13114.8 (4)C16—C19—H19C109.5
C13—C16—C17'107.0 (4)C17—C19—H19C71.7
C19—C16—C1759.3 (9)H19A—C19—H19C109.5
C18—C16—C17106.7 (8)H19B—C19—H19C109.5
C13—C16—C17107.8 (5)C16—C19'—H19D109.5
C13—C16—C18'108.4 (3)C16—C19'—H19E109.5
C17'—C16—C18'103.9 (5)H19D—C19'—H19E109.5
C13—C16—C19'111.1 (3)C16—C19'—H19F109.5
C17'—C16—C19'134.6 (6)H19D—C19'—H19F109.5
C18'—C16—C19'86.8 (6)H19E—C19'—H19F109.5
C1—N1—C10—C1182.3 (3)C9—C4—C5—C62.0 (3)
C3—N1—C10—C1198.5 (3)C1—C4—C5—C6179.9 (2)
C1—N1—C10—C1591.3 (3)C11—C10—C15—C143.5 (4)
C3—N1—C10—C1588.0 (3)N1—C10—C15—C14170.1 (2)
C2—N2—C1—N11.1 (2)C5—C6—C7—C80.3 (4)
C2—N2—C1—C4178.75 (19)Cl2—C6—C7—C8178.4 (2)
C3—N1—C1—N20.7 (2)C10—C15—C14—C130.2 (4)
C10—N1—C1—N2179.92 (19)C12—C13—C14—C153.2 (4)
C3—N1—C1—C4179.1 (2)C16—C13—C14—C15174.6 (2)
C10—N1—C1—C40.3 (3)C4—C9—C8—C70.1 (4)
N2—C1—C4—C9170.3 (2)C4—C9—C8—Cl1178.79 (19)
N1—C1—C4—C99.5 (4)C6—C7—C8—C90.6 (4)
N2—C1—C4—C57.5 (3)C6—C7—C8—Cl1178.3 (2)
N1—C1—C4—C5172.7 (2)C14—C13—C16—C197.5 (8)
C5—C4—C9—C81.2 (4)C12—C13—C16—C19170.1 (7)
C1—C4—C9—C8179.0 (2)C14—C13—C16—C18170.2 (6)
C1—N1—C3—C20.1 (2)C12—C13—C16—C1812.2 (7)
C10—N1—C3—C2179.45 (18)C14—C13—C16—C17'119.1 (5)
C1—N1—C3—C20179.06 (18)C12—C13—C16—C17'58.6 (6)
C10—N1—C3—C201.6 (3)C14—C13—C16—C1771.2 (8)
C21—C20—C3—C298.9 (3)C12—C13—C16—C17106.5 (7)
C25—C20—C3—C279.8 (3)C14—C13—C16—C18'129.4 (4)
C21—C20—C3—N182.4 (3)C12—C13—C16—C18'52.9 (5)
C25—C20—C3—N198.9 (3)C14—C13—C16—C19'35.7 (6)
N1—C3—C2—N20.6 (2)C12—C13—C16—C19'146.6 (5)
C20—C3—C2—N2178.3 (2)C31—C26—C27—C280.4 (4)
N1—C3—C2—C26178.7 (2)C2—C26—C27—C28177.6 (2)
C20—C3—C2—C262.5 (4)C27—C26—C31—C300.1 (4)
C1—N2—C2—C31.0 (2)C2—C26—C31—C30177.4 (2)
C1—N2—C2—C26178.30 (19)C21—C20—C25—C240.5 (4)
C15—C10—C11—C123.3 (4)C3—C20—C25—C24178.3 (3)
N1—C10—C11—C12170.3 (2)C20—C25—C24—C230.7 (5)
C10—C11—C12—C130.2 (4)C22—C23—C24—C251.1 (5)
C14—C13—C12—C113.4 (4)C25—C20—C21—C221.2 (4)
C16—C13—C12—C11174.4 (2)C3—C20—C21—C22177.5 (2)
C3—C2—C26—C31163.2 (2)C24—C23—C22—C210.4 (5)
N2—C2—C26—C3117.6 (3)C20—C21—C22—C230.8 (5)
C3—C2—C26—C2719.6 (4)C26—C27—C28—C290.0 (5)
N2—C2—C26—C27159.5 (2)C27—C28—C29—C300.6 (5)
C7—C6—C5—O1176.8 (2)C28—C29—C30—C310.9 (5)
Cl2—C6—C5—O11.3 (3)C26—C31—C30—C290.5 (4)
C7—C6—C5—C41.6 (4)C18—C16—C17—C19128.7 (8)
Cl2—C6—C5—C4179.73 (18)C13—C16—C17—C19107.5 (6)
C9—C4—C5—O1176.3 (2)C18—C16—C19—C1785.5 (11)
C1—C4—C5—O11.6 (3)C13—C16—C19—C1797.3 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N20.821.812.541 (2)147
C29—H29···Cl2i0.932.973.705 (3)137
Symmetry code: (i) x+2, y1, z.
 

References

First citationBastide, M., Jouvert, S. & Bastide, J. M. (1982). Can. J. Microbiol. 28, 1119–1126.  CrossRef CAS PubMed Google Scholar
First citationBruker. (1998). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSheldrick, G. M. (2015). Acta Cryst. C71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar

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