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

Journal logoIUCrDATA
ISSN: 2414-3146

2-[4,5-Bis(4-bromo­phen­yl)-1-(4-tert-but­ylphen­yl)-1H-imidazol-2-yl]-4,6-di­chloro­phenol

aDepartment of Studies in 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 28 November 2019; accepted 13 December 2019; online 24 December 2019)

In the title compound, C31H24Br2Cl2N2O, the dihedral angles subtended by the tert-butyl-phenyl, 4,6-di­chloro­phenol and 4-bromo­phenyl (×2) rings are 70.7 (3), 8.1 (3), 28.1 (3) and 84.2 (3)°, respectively. The orientations of the pendant rings may be related to intra­molecular O—H⋯N and C—H⋯π inter­actions. One of the tert-butyl methyl groups is disordered over two sets of sites in a 0.54 (3):0.46 (3) ratio. In the crystal, a weak C—H⋯π inter­action generates inversion dimers.

Keywords: crystal structure.

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

Structure description

Imidazole and its derivatives play an important role in natural product chemistry (e.g. Brown et al., 1998[Brown, E. G. (1998). Ring Nitrogen and Key Biomolecules, ch. 2. Boston: Kluwer Academic Publishers.]; Forte et al., 2009[Forte, B., Malgesini, B., Piutti, C., Quartieri, F., Scolaro, A. & Papeo, G. A. (2009). Marine Drugs, 7, 705-753.]). As part of our studies in this area, we now report the synthesis and structure of the title compound, which consists of an imidazole ring bearing C4–C9 tert-butyl­phenyl, C14–C19 4,6-di­chloro­phenol and C2–C25 and C26–C31 4-bromo­phenyl rings (Fig. 1[link]). The dihedral angles between the imidazole core and these four rings are 70.7 (3), 8.1 (3), 28.1 (3) and 84.2 (3)°, respectively. An intra­molecular O—H⋯N hydrogen bond (Table 1[link]) may help to establish the near-coplanarity of the imidazole and C14 rings and an intra­molecular C—H⋯π inter­action may help to establish the near-orthogonal relationship between the imidazole and C4 ring. The C11 tert-butyl methyl group is disordered over two sets of sites in a 0.54 (3):0.46 (3) ratio. In the crystal, a weak C—H⋯π inter­action generates inversion dimers but there are no aromatic ππ stacking inter­actions (Fig. 2[link]). A very weak C27—H27⋯N2 hydrogen bond is also present.

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 and Cg4 are the centroids of the C4–C9 and C20–C25 rings, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1⋯N2 0.82 1.81 2.542 (7) 148
C27—H27⋯N2i 0.93 2.68 3.547 (6) 156
C15—H15⋯Cg2 0.93 2.76 3.621 (7) 154
C9—H9⋯Cg4ii 0.93 2.85 3.641 (6) 144
Symmetry codes: (i) -x+1, -y+2, -z; (ii) [x+{\script{3\over 2}}, y+{\script{5\over 2}}, z].
[Figure 1]
Figure 1
The mol­ecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level.
[Figure 2]
Figure 2
Unit-cell packing of the title compound showing inter­molecular C—H⋯N inter­actions with dotted lines. H atoms not involved in hydrogen bonding have been excluded.

Synthesis and crystallization

1,2-Bis­(4-bromo­phen­yl)ethane-1,2-dione (10 mmol), 4-tert-butyl­aniline (10 mmol) and 3,5-di­chloro-2-hy­droxy­benzalde­hyde (10 mmol) along with ammonium acetate (10 mmol) in acetic acid (15 ml) were refluxed at room temperature for 6 h. The progress of the reaction was monitored by TLC (7:3 petroleum ether: ethyl acetate). On completion, the reaction mixture was poured onto ice-cold water, the obtained precipitate was filtered, dried and purified by column chromatography (7:3 petroleum ether: ethyl acetate), giving a yield of 80%. The compound was recrystallized from ethanol solution. 1H-NMR (CDCl3): δ 1.26 (s, 9H), 6.07 (s, OH), 7.26–7.38 (m, 6H), 3.97–4.03 (q, 8H).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link].

Table 2
Experimental details

Crystal data
Chemical formula C31H24Br2Cl2N2O
Mr 671.24
Crystal system, space group Monoclinic, C2/c
Temperature (K) 373
a, b, c (Å) 17.7619 (5), 12.7435 (4), 28.2194 (8)
β (°) 102.478 (2)
V3) 6236.5 (3)
Z 8
Radiation type Mo Kα
μ (mm−1) 2.80
Crystal size (mm) 0.16 × 0.15 × 0.14
 
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 0.646, 0.676
No. of measured, independent and observed [I > 2σ(I)] reflections 38305, 3839, 3305
Rint 0.038
(sin θ/λ)max−1) 0.595
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.064, 0.239, 1.15
No. of reflections 3839
No. of parameters 353
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 2.03, −0.53
Computer programs: SMART and SAINT-Plus (Bruker, 1998[Bruker. (1998). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXLT (Sheldrick, 2015a[Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.]), SHELXL2018/3 (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]), ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and CAMERON (Watkin et al., 1996[Watkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON. Chemical Crystallography Laboratory, University of Oxford, England.]).

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: SHELXLT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: CAMERON (Watkin et al., 1996).

2-[4,5-Bis(4-bromophenyl)-1-(4-tert-butylphenyl)-1H-imidazol-2-yl]-4,6-dichlorophenol top
Crystal data top
C31H24Br2Cl2N2OF(000) = 2688
Mr = 671.24Dx = 1.430 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 17.7619 (5) ÅCell parameters from 3839 reflections
b = 12.7435 (4) Åθ = 2.0–22.0°
c = 28.2194 (8) ŵ = 2.80 mm1
β = 102.478 (2)°T = 373 K
V = 6236.5 (3) Å3Block, colorless
Z = 80.16 × 0.15 × 0.14 mm
Data collection top
Bruker SMART APEX CCD
diffractometer
3305 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.038
ω scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 1998)
h = 1818
Tmin = 0.646, Tmax = 0.676k = 1313
38305 measured reflectionsl = 2929
3839 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.064H-atom parameters constrained
wR(F2) = 0.239 w = 1/[σ2(Fo2) + (0.1772P)2 + 7.3582P]
where P = (Fo2 + 2Fc2)/3
S = 1.15(Δ/σ)max < 0.001
3839 reflectionsΔρmax = 2.03 e Å3
353 parametersΔρmin = 0.53 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)
Br20.37961 (5)0.94032 (8)0.22600 (3)0.0880 (4)
Br10.23913 (4)0.66001 (7)0.09750 (3)0.0874 (4)
Cl10.83979 (12)0.86713 (16)0.08924 (7)0.0808 (6)
Cl20.93419 (14)1.0667 (2)0.07944 (9)0.1126 (10)
N10.6357 (3)0.9183 (4)0.07290 (16)0.0441 (11)
C10.6612 (3)0.8957 (4)0.03174 (19)0.0438 (13)
N20.6050 (3)0.8543 (4)0.00143 (17)0.0465 (12)
C20.5402 (3)0.8518 (4)0.0183 (2)0.0459 (14)
C30.5576 (3)0.8907 (4)0.0646 (2)0.0438 (13)
C40.6785 (3)0.9547 (4)0.11935 (19)0.0431 (13)
C140.7370 (3)0.9191 (4)0.0217 (2)0.0464 (14)
C210.4692 (4)0.7306 (5)0.0446 (2)0.0558 (15)
H210.5163630.7086110.0502850.067*
C260.5132 (3)0.9005 (4)0.10235 (19)0.0426 (13)
C250.3960 (4)0.8382 (5)0.0018 (2)0.0555 (16)
H250.3940350.8895680.0212730.067*
C290.4321 (3)0.9217 (5)0.1747 (2)0.0520 (15)
C230.3317 (4)0.7187 (5)0.0614 (2)0.0586 (16)
C190.7511 (3)0.8830 (4)0.0234 (2)0.0467 (14)
C200.4676 (3)0.8068 (5)0.0095 (2)0.0472 (14)
C160.8641 (4)0.9950 (5)0.0397 (3)0.0634 (18)
C310.5155 (4)0.8252 (5)0.1367 (2)0.0586 (16)
H310.5447100.7649700.1356770.070*
C180.8229 (3)0.9081 (5)0.0342 (2)0.0525 (15)
C150.7941 (4)0.9753 (5)0.0527 (2)0.0556 (16)
H150.7856740.9997130.0822000.067*
C70.7660 (4)1.0275 (5)0.2066 (2)0.0523 (15)
C50.7312 (4)0.8902 (5)0.1474 (2)0.0548 (15)
H50.7377650.8219490.1373790.066*
C300.4755 (4)0.8365 (5)0.1730 (3)0.0649 (18)
H300.4786050.7846160.1964670.078*
C240.3288 (4)0.7958 (5)0.0271 (2)0.0578 (16)
H240.2817290.8181760.0214130.069*
C270.4672 (4)0.9865 (5)0.1043 (2)0.0644 (17)
H270.4634751.0381390.0805970.077*
C60.7747 (4)0.9267 (5)0.1906 (2)0.0579 (16)
H60.8107830.8825070.2094540.069*
C90.6670 (4)1.0540 (5)0.1352 (2)0.0553 (16)
H90.6299491.0975890.1167730.066*
C280.4262 (4)0.9985 (6)0.1405 (3)0.0646 (17)
H280.3955131.0572690.1414950.077*
C170.8784 (4)0.9612 (5)0.0025 (2)0.0573 (16)
H170.9260120.9740230.0099860.069*
C80.7105 (4)1.0880 (5)0.1781 (3)0.0633 (18)
H80.7021011.1553540.1886170.076*
C220.4018 (4)0.6868 (5)0.0711 (2)0.0605 (17)
H220.4033470.6369370.0949180.073*
C100.8204 (4)1.0707 (6)0.2521 (3)0.074 (2)
C130.7885 (7)1.1621 (8)0.2744 (3)0.105 (3)
H13A0.7836921.2211590.2528590.158*
H13B0.8226291.1797050.3046640.158*
H13C0.7387211.1442850.2801670.158*
C120.8438 (6)0.9853 (10)0.2916 (3)0.114 (4)
H12A0.7982500.9543860.2988110.170*
H12B0.8740701.0164950.3204520.170*
H12C0.8735260.9320200.2799960.170*
C110.888 (2)1.133 (3)0.2282 (14)0.099 (7)0.46 (3)
H11A0.8639191.1842170.2048670.148*0.46 (3)
H11B0.9151471.0828750.2125850.148*0.46 (3)
H11C0.9244491.1676960.2536780.148*0.46 (3)
C11'0.8959 (19)1.086 (3)0.2423 (11)0.099 (7)0.54 (3)
H11D0.9264041.1280180.2674900.148*0.54 (3)
H11E0.8912221.1208560.2116350.148*0.54 (3)
H11F0.9202991.0190540.2411500.148*0.54 (3)
O10.7002 (3)0.8310 (3)0.05618 (15)0.0588 (11)
H10.6609770.8212590.0459300.088*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br20.0757 (6)0.1339 (8)0.0630 (6)0.0197 (5)0.0340 (5)0.0061 (4)
Br10.0554 (6)0.1039 (7)0.0923 (7)0.0211 (4)0.0076 (4)0.0165 (4)
Cl10.0874 (14)0.0892 (12)0.0797 (13)0.0099 (10)0.0485 (11)0.0157 (10)
Cl20.0775 (14)0.166 (2)0.0940 (16)0.0665 (15)0.0169 (12)0.0298 (15)
N10.041 (3)0.054 (3)0.035 (3)0.006 (2)0.004 (2)0.001 (2)
C10.043 (3)0.051 (3)0.036 (3)0.001 (3)0.004 (3)0.000 (2)
N20.045 (3)0.054 (3)0.039 (3)0.006 (2)0.006 (2)0.005 (2)
C20.044 (3)0.053 (3)0.038 (3)0.001 (2)0.004 (3)0.005 (2)
C30.041 (3)0.051 (3)0.038 (3)0.000 (3)0.004 (2)0.004 (2)
C40.042 (3)0.052 (3)0.035 (3)0.010 (3)0.007 (3)0.002 (2)
C140.044 (3)0.050 (3)0.044 (3)0.004 (3)0.007 (3)0.007 (3)
C210.052 (4)0.059 (4)0.056 (4)0.000 (3)0.009 (3)0.004 (3)
C260.037 (3)0.051 (3)0.038 (3)0.003 (3)0.004 (2)0.005 (3)
C250.051 (4)0.067 (4)0.047 (3)0.004 (3)0.009 (3)0.001 (3)
C290.043 (3)0.071 (4)0.041 (3)0.001 (3)0.008 (3)0.003 (3)
C230.049 (4)0.065 (4)0.057 (4)0.012 (3)0.000 (3)0.005 (3)
C190.048 (3)0.046 (3)0.045 (3)0.003 (3)0.007 (3)0.005 (3)
C200.041 (3)0.058 (3)0.040 (3)0.003 (3)0.003 (3)0.010 (3)
C160.047 (4)0.072 (4)0.068 (4)0.018 (3)0.004 (3)0.001 (4)
C310.052 (4)0.061 (4)0.065 (4)0.011 (3)0.017 (3)0.005 (3)
C180.048 (4)0.054 (3)0.061 (4)0.004 (3)0.024 (3)0.007 (3)
C150.052 (4)0.064 (4)0.050 (4)0.011 (3)0.010 (3)0.003 (3)
C70.049 (4)0.068 (4)0.041 (3)0.016 (3)0.012 (3)0.005 (3)
C50.060 (4)0.048 (3)0.052 (4)0.004 (3)0.002 (3)0.003 (3)
C300.070 (5)0.074 (4)0.058 (4)0.003 (4)0.031 (4)0.020 (3)
C240.040 (3)0.076 (4)0.057 (4)0.003 (3)0.008 (3)0.004 (3)
C270.076 (5)0.065 (4)0.054 (4)0.007 (4)0.017 (3)0.012 (3)
C60.062 (4)0.060 (4)0.046 (4)0.007 (3)0.002 (3)0.004 (3)
C90.060 (4)0.051 (4)0.053 (4)0.005 (3)0.008 (3)0.000 (3)
C280.059 (4)0.075 (4)0.063 (4)0.013 (3)0.020 (3)0.004 (4)
C170.047 (4)0.062 (4)0.068 (4)0.006 (3)0.023 (3)0.005 (3)
C80.070 (4)0.054 (4)0.065 (4)0.006 (3)0.012 (4)0.017 (3)
C220.053 (4)0.066 (4)0.059 (4)0.003 (3)0.004 (3)0.009 (3)
C100.064 (4)0.099 (5)0.058 (4)0.028 (4)0.010 (4)0.026 (4)
C130.117 (8)0.107 (7)0.081 (6)0.015 (5)0.001 (5)0.043 (5)
C120.110 (8)0.145 (9)0.065 (5)0.013 (6)0.028 (5)0.028 (6)
C110.091 (10)0.11 (2)0.092 (16)0.072 (16)0.019 (11)0.005 (12)
C11'0.091 (10)0.11 (2)0.092 (16)0.072 (16)0.019 (11)0.005 (12)
O10.057 (3)0.071 (3)0.048 (2)0.012 (2)0.011 (2)0.008 (2)
Geometric parameters (Å, º) top
Br2—C291.899 (6)C18—C171.361 (9)
Br1—C231.891 (6)C15—H150.9300
Cl1—C181.725 (6)C7—C81.368 (10)
Cl2—C161.743 (6)C7—C61.380 (9)
N1—C11.365 (7)C7—C101.532 (9)
N1—C31.400 (7)C5—C61.375 (9)
N1—C41.443 (7)C5—H50.9300
C1—N21.321 (7)C30—H300.9300
C1—C141.466 (8)C24—H240.9300
N2—C21.383 (7)C27—C281.386 (10)
C2—C31.369 (8)C27—H270.9300
C2—C201.473 (8)C6—H60.9300
C3—C261.462 (8)C9—C81.359 (10)
C4—C51.364 (9)C9—H90.9300
C4—C91.371 (8)C28—H280.9300
C14—C151.388 (9)C17—H170.9300
C14—C191.424 (8)C8—H80.9300
C21—C221.385 (9)C22—H220.9300
C21—C201.391 (9)C10—C11'1.44 (3)
C21—H210.9300C10—C131.493 (12)
C26—C311.359 (9)C10—C121.550 (14)
C26—C271.375 (9)C10—C111.70 (3)
C25—C241.362 (9)C13—H13A0.9600
C25—C201.395 (9)C13—H13B0.9600
C25—H250.9300C13—H13C0.9600
C29—C301.338 (9)C12—H12A0.9600
C29—C281.362 (9)C12—H12B0.9600
C23—C241.387 (10)C12—H12C0.9600
C23—C221.393 (9)C11—H11A0.9600
C19—O11.323 (7)C11—H11B0.9600
C19—C181.410 (8)C11—H11C0.9600
C16—C171.339 (10)C11'—H11D0.9600
C16—C151.395 (9)C11'—H11E0.9600
C31—C301.373 (9)C11'—H11F0.9600
C31—H310.9300O1—H10.8200
C1—N1—C3107.6 (4)C31—C30—H30119.7
C1—N1—C4129.4 (5)C25—C24—C23119.1 (6)
C3—N1—C4122.8 (5)C25—C24—H24120.5
N2—C1—N1110.4 (5)C23—C24—H24120.5
N2—C1—C14121.9 (5)C26—C27—C28121.9 (6)
N1—C1—C14127.5 (5)C26—C27—H27119.1
C1—N2—C2106.9 (5)C28—C27—H27119.1
C3—C2—N2109.9 (5)C5—C6—C7121.6 (6)
C3—C2—C20129.8 (5)C5—C6—H6119.2
N2—C2—C20120.2 (5)C7—C6—H6119.2
C2—C3—N1105.2 (5)C8—C9—C4119.3 (6)
C2—C3—C26132.9 (5)C8—C9—H9120.3
N1—C3—C26121.9 (5)C4—C9—H9120.3
C5—C4—C9119.9 (6)C29—C28—C27118.1 (6)
C5—C4—N1119.6 (5)C29—C28—H28121.0
C9—C4—N1120.5 (5)C27—C28—H28121.0
C15—C14—C19119.0 (5)C16—C17—C18119.7 (6)
C15—C14—C1124.0 (5)C16—C17—H17120.2
C19—C14—C1117.0 (5)C18—C17—H17120.2
C22—C21—C20121.2 (6)C9—C8—C7122.8 (6)
C22—C21—H21119.4C9—C8—H8118.6
C20—C21—H21119.4C7—C8—H8118.6
C31—C26—C27117.5 (6)C21—C22—C23118.8 (6)
C31—C26—C3121.4 (5)C21—C22—H22120.6
C27—C26—C3121.1 (5)C23—C22—H22120.6
C24—C25—C20122.0 (6)C11'—C10—C13115.5 (14)
C24—C25—H25119.0C11'—C10—C7109.4 (13)
C20—C25—H25119.0C13—C10—C7114.0 (7)
C30—C29—C28120.9 (6)C11'—C10—C1296.7 (16)
C30—C29—Br2120.8 (5)C13—C10—C12108.1 (7)
C28—C29—Br2118.3 (5)C7—C10—C12111.9 (6)
C24—C23—C22120.9 (6)C13—C10—C1199.7 (17)
C24—C23—Br1119.8 (5)C7—C10—C11102.0 (13)
C22—C23—Br1119.2 (5)C12—C10—C11120.7 (17)
O1—C19—C18118.4 (5)C10—C13—H13A109.5
O1—C19—C14124.1 (5)C10—C13—H13B109.5
C18—C19—C14117.5 (5)H13A—C13—H13B109.5
C21—C20—C25118.0 (5)C10—C13—H13C109.5
C21—C20—C2120.1 (5)H13A—C13—H13C109.5
C25—C20—C2121.9 (5)H13B—C13—H13C109.5
C17—C16—C15121.8 (6)C10—C12—H12A109.5
C17—C16—Cl2119.6 (5)C10—C12—H12B109.5
C15—C16—Cl2118.5 (5)H12A—C12—H12B109.5
C26—C31—C30121.1 (6)C10—C12—H12C109.5
C26—C31—H31119.5H12A—C12—H12C109.5
C30—C31—H31119.5H12B—C12—H12C109.5
C17—C18—C19122.1 (6)C10—C11—H11A109.5
C17—C18—Cl1120.1 (5)C10—C11—H11B109.5
C19—C18—Cl1117.9 (5)H11A—C11—H11B109.5
C14—C15—C16119.9 (6)C10—C11—H11C109.5
C14—C15—H15120.1H11A—C11—H11C109.5
C16—C15—H15120.1H11B—C11—H11C109.5
C8—C7—C6116.7 (6)C10—C11'—H11D109.5
C8—C7—C10122.2 (6)C10—C11'—H11E109.5
C6—C7—C10121.0 (6)H11D—C11'—H11E109.5
C4—C5—C6119.6 (6)C10—C11'—H11F109.5
C4—C5—H5120.2H11D—C11'—H11F109.5
C6—C5—H5120.2H11E—C11'—H11F109.5
C29—C30—C31120.5 (6)C19—O1—H1109.5
C29—C30—H30119.7
C3—N1—C1—N21.0 (6)C14—C19—C18—C172.4 (9)
C4—N1—C1—N2173.7 (5)O1—C19—C18—Cl10.9 (7)
C3—N1—C1—C14174.4 (5)C14—C19—C18—Cl1178.7 (4)
C4—N1—C1—C1410.9 (9)C19—C14—C15—C160.4 (9)
N1—C1—N2—C21.3 (6)C1—C14—C15—C16179.1 (6)
C14—C1—N2—C2174.4 (5)C17—C16—C15—C140.1 (10)
C1—N2—C2—C31.0 (6)Cl2—C16—C15—C14179.5 (5)
C1—N2—C2—C20178.2 (5)C9—C4—C5—C62.5 (9)
N2—C2—C3—N10.4 (6)N1—C4—C5—C6176.8 (5)
C20—C2—C3—N1177.3 (5)C28—C29—C30—C310.4 (11)
N2—C2—C3—C26176.0 (6)Br2—C29—C30—C31177.7 (5)
C20—C2—C3—C260.8 (10)C26—C31—C30—C291.1 (11)
C1—N1—C3—C20.4 (6)C20—C25—C24—C230.3 (9)
C4—N1—C3—C2174.8 (5)C22—C23—C24—C251.8 (10)
C1—N1—C3—C26177.3 (5)Br1—C23—C24—C25179.2 (5)
C4—N1—C3—C262.1 (8)C31—C26—C27—C281.8 (10)
C1—N1—C4—C567.3 (8)C3—C26—C27—C28178.3 (6)
C3—N1—C4—C5106.7 (6)C4—C5—C6—C70.4 (10)
C1—N1—C4—C9112.0 (7)C8—C7—C6—C52.0 (10)
C3—N1—C4—C974.0 (7)C10—C7—C6—C5173.7 (6)
N2—C1—C14—C15170.8 (6)C5—C4—C9—C82.2 (9)
N1—C1—C14—C154.1 (9)N1—C4—C9—C8177.2 (6)
N2—C1—C14—C197.9 (8)C30—C29—C28—C270.8 (10)
N1—C1—C14—C19177.2 (5)Br2—C29—C28—C27177.4 (5)
C2—C3—C26—C3193.4 (8)C26—C27—C28—C290.4 (11)
N1—C3—C26—C3182.5 (7)C15—C16—C17—C181.5 (10)
C2—C3—C26—C2786.5 (8)Cl2—C16—C17—C18178.0 (5)
N1—C3—C26—C2797.6 (7)C19—C18—C17—C162.8 (10)
C15—C14—C19—O1178.4 (5)Cl1—C18—C17—C16178.3 (5)
C1—C14—C19—O10.4 (8)C4—C9—C8—C70.3 (10)
C15—C14—C19—C180.8 (8)C6—C7—C8—C92.3 (10)
C1—C14—C19—C18178.0 (5)C10—C7—C8—C9173.3 (7)
C22—C21—C20—C250.1 (9)C20—C21—C22—C231.4 (10)
C22—C21—C20—C2179.8 (6)C24—C23—C22—C212.3 (10)
C24—C25—C20—C210.6 (9)Br1—C23—C22—C21179.7 (5)
C24—C25—C20—C2179.2 (5)C8—C7—C10—C11'105.9 (17)
C3—C2—C20—C21150.0 (6)C6—C7—C10—C11'69.6 (17)
N2—C2—C20—C2126.6 (8)C8—C7—C10—C1325.1 (10)
C3—C2—C20—C2529.9 (9)C6—C7—C10—C13159.5 (7)
N2—C2—C20—C25153.5 (5)C8—C7—C10—C12148.2 (7)
C27—C26—C31—C302.2 (10)C6—C7—C10—C1236.3 (9)
C3—C26—C31—C30177.9 (6)C8—C7—C10—C1181.4 (18)
O1—C19—C18—C17179.9 (6)C6—C7—C10—C1194.0 (18)
Hydrogen-bond geometry (Å, º) top
Cg2 and Cg4 are the centroids of the C4–C9 and C20–C25 rings, respectively.
D—H···AD—HH···AD···AD—H···A
O1—H1···N20.821.812.542 (7)148
C27—H27···N2i0.932.683.547 (6)156
C15—H15···Cg20.932.763.621 (7)154
C9—H9···Cg4ii0.932.853.641 (6)144
Symmetry codes: (i) x+1, y+2, z; (ii) x+3/2, y+5/2, z.
 

References

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