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

Devika, S.; Shraddha, K.N.; Begum, N.S.

doi:10.1107/S2414314619016729

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 4| Part 12| December 2019| x191672

https://doi.org/10.1107/S2414314619016729

Open

access

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

S. Devika,^a K. N. Shraddha ^a and Noor Shahina Begum ^a ^*

^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.

CCDC reference: 1950454

Structure description

Imidazole and its derivatives play an important role in natural product chemistry (e.g. Brown et al., 1998 ; Forte et al., 2009 ). 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). 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) 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 π–π stacking interactions (Fig. 2). 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	D⋯A	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
The molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level.

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.

Table 2
Experimental details

Crystal data
Chemical formula	C₃₁H₂₄Br₂Cl₂N₂O
M_r	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)
V (Å³)	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 )
T_min, T_max	0.646, 0.676
No. of measured, independent and observed [I > 2σ(I)] reflections	38305, 3839, 3305
R_int	0.038
(sin θ/λ)_max (Å⁻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
Δρ_max, Δρ_min (e Å⁻³)	2.03, −0.53
Computer programs: SMART and SAINT-Plus (Bruker, 1998), SHELXLT (Sheldrick, 2015a ), SHELXL2018/3 (Sheldrick, 2015b ), ORTEP-3 for Windows (Farrugia, 2012 ) and CAMERON (Watkin et al., 1996 ).

Structural data

CCDC reference: 1950454

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314619016729/hb4331sup1.cif

Supporting information file. DOI: https://doi.org/10.1107/S2414314619016729/hb4331sup3.jpg

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314619016729/hb4331Isup4.hkl

checkCIF report

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

C₃₁H₂₄Br₂Cl₂N₂O	F(000) = 2688
M_r = 671.24	D_x = 1.430 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 17.7619 (5) Å	Cell parameters from 3839 reflections
b = 12.7435 (4) Å	θ = 2.0–22.0°
c = 28.2194 (8) Å	µ = 2.80 mm⁻¹
β = 102.478 (2)°	T = 373 K
V = 6236.5 (3) Å³	Block, colorless
Z = 8	0.16 × 0.15 × 0.14 mm

Data collection top

Bruker SMART APEX CCD diffractometer	3305 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.038
ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −18→18
T_min = 0.646, T_max = 0.676	k = −13→13
38305 measured reflections	l = −29→29
3839 independent reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.064	H-atom parameters constrained
wR(F²) = 0.239	w = 1/[σ²(F_o²) + (0.1772P)² + 7.3582P] where P = (F_o² + 2F_c²)/3
S = 1.15	(Δ/σ)_max < 0.001
3839 reflections	Δρ_max = 2.03 e Å⁻³
353 parameters	Δρ_min = −0.53 e Å⁻³

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Br2	0.37961 (5)	0.94032 (8)	0.22600 (3)	0.0880 (4)
Br1	0.23913 (4)	0.66001 (7)	−0.09750 (3)	0.0874 (4)
Cl1	0.83979 (12)	0.86713 (16)	−0.08924 (7)	0.0808 (6)
Cl2	0.93419 (14)	1.0667 (2)	0.07944 (9)	0.1126 (10)
N1	0.6357 (3)	0.9183 (4)	0.07290 (16)	0.0441 (11)
C1	0.6612 (3)	0.8957 (4)	0.03174 (19)	0.0438 (13)
N2	0.6050 (3)	0.8543 (4)	−0.00143 (17)	0.0465 (12)
C2	0.5402 (3)	0.8518 (4)	0.0183 (2)	0.0459 (14)
C3	0.5576 (3)	0.8907 (4)	0.0646 (2)	0.0438 (13)
C4	0.6785 (3)	0.9547 (4)	0.11935 (19)	0.0431 (13)
C14	0.7370 (3)	0.9191 (4)	0.0217 (2)	0.0464 (14)
C21	0.4692 (4)	0.7306 (5)	−0.0446 (2)	0.0558 (15)
H21	0.516363	0.708611	−0.050285	0.067*
C26	0.5132 (3)	0.9005 (4)	0.10235 (19)	0.0426 (13)
C25	0.3960 (4)	0.8382 (5)	−0.0018 (2)	0.0555 (16)
H25	0.394035	0.889568	0.021273	0.067*
C29	0.4321 (3)	0.9217 (5)	0.1747 (2)	0.0520 (15)
C23	0.3317 (4)	0.7187 (5)	−0.0614 (2)	0.0586 (16)
C19	0.7511 (3)	0.8830 (4)	−0.0234 (2)	0.0467 (14)
C20	0.4676 (3)	0.8068 (5)	−0.0095 (2)	0.0472 (14)
C16	0.8641 (4)	0.9950 (5)	0.0397 (3)	0.0634 (18)
C31	0.5155 (4)	0.8252 (5)	0.1367 (2)	0.0586 (16)
H31	0.544710	0.764970	0.135677	0.070*
C18	0.8229 (3)	0.9081 (5)	−0.0342 (2)	0.0525 (15)
C15	0.7941 (4)	0.9753 (5)	0.0527 (2)	0.0556 (16)
H15	0.785674	0.999713	0.082200	0.067*
C7	0.7660 (4)	1.0275 (5)	0.2066 (2)	0.0523 (15)
C5	0.7312 (4)	0.8902 (5)	0.1474 (2)	0.0548 (15)
H5	0.737765	0.821949	0.137379	0.066*
C30	0.4755 (4)	0.8365 (5)	0.1730 (3)	0.0649 (18)
H30	0.478605	0.784616	0.196467	0.078*
C24	0.3288 (4)	0.7958 (5)	−0.0271 (2)	0.0578 (16)
H24	0.281729	0.818176	−0.021413	0.069*
C27	0.4672 (4)	0.9865 (5)	0.1043 (2)	0.0644 (17)
H27	0.463475	1.038139	0.080597	0.077*
C6	0.7747 (4)	0.9267 (5)	0.1906 (2)	0.0579 (16)
H6	0.810783	0.882507	0.209454	0.069*
C9	0.6670 (4)	1.0540 (5)	0.1352 (2)	0.0553 (16)
H9	0.629949	1.097589	0.116773	0.066*
C28	0.4262 (4)	0.9985 (6)	0.1405 (3)	0.0646 (17)
H28	0.395513	1.057269	0.141495	0.077*
C17	0.8784 (4)	0.9612 (5)	−0.0025 (2)	0.0573 (16)
H17	0.926012	0.974023	−0.009986	0.069*
C8	0.7105 (4)	1.0880 (5)	0.1781 (3)	0.0633 (18)
H8	0.702101	1.155354	0.188617	0.076*
C22	0.4018 (4)	0.6868 (5)	−0.0711 (2)	0.0605 (17)
H22	0.403347	0.636937	−0.094918	0.073*
C10	0.8204 (4)	1.0707 (6)	0.2521 (3)	0.074 (2)
C13	0.7885 (7)	1.1621 (8)	0.2744 (3)	0.105 (3)
H13A	0.783692	1.221159	0.252859	0.158*
H13B	0.822629	1.179705	0.304664	0.158*
H13C	0.738721	1.144285	0.280167	0.158*
C12	0.8438 (6)	0.9853 (10)	0.2916 (3)	0.114 (4)
H12A	0.798250	0.954386	0.298811	0.170*
H12B	0.874070	1.016495	0.320452	0.170*
H12C	0.873526	0.932020	0.279996	0.170*
C11	0.888 (2)	1.133 (3)	0.2282 (14)	0.099 (7)	0.46 (3)
H11A	0.863919	1.184217	0.204867	0.148*	0.46 (3)
H11B	0.915147	1.082875	0.212585	0.148*	0.46 (3)
H11C	0.924449	1.167696	0.253678	0.148*	0.46 (3)
C11'	0.8959 (19)	1.086 (3)	0.2423 (11)	0.099 (7)	0.54 (3)
H11D	0.926404	1.128018	0.267490	0.148*	0.54 (3)
H11E	0.891222	1.120856	0.211635	0.148*	0.54 (3)
H11F	0.920299	1.019054	0.241150	0.148*	0.54 (3)
O1	0.7002 (3)	0.8310 (3)	−0.05618 (15)	0.0588 (11)
H1	0.660977	0.821259	−0.045930	0.088*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br2	0.0757 (6)	0.1339 (8)	0.0630 (6)	0.0197 (5)	0.0340 (5)	0.0061 (4)
Br1	0.0554 (6)	0.1039 (7)	0.0923 (7)	−0.0211 (4)	−0.0076 (4)	−0.0165 (4)
Cl1	0.0874 (14)	0.0892 (12)	0.0797 (13)	−0.0099 (10)	0.0485 (11)	−0.0157 (10)
Cl2	0.0775 (14)	0.166 (2)	0.0940 (16)	−0.0665 (15)	0.0169 (12)	−0.0298 (15)
N1	0.041 (3)	0.054 (3)	0.035 (3)	−0.006 (2)	0.004 (2)	−0.001 (2)
C1	0.043 (3)	0.051 (3)	0.036 (3)	−0.001 (3)	0.004 (3)	0.000 (2)
N2	0.045 (3)	0.054 (3)	0.039 (3)	−0.006 (2)	0.006 (2)	0.005 (2)
C2	0.044 (3)	0.053 (3)	0.038 (3)	−0.001 (2)	0.004 (3)	0.005 (2)
C3	0.041 (3)	0.051 (3)	0.038 (3)	0.000 (3)	0.004 (2)	0.004 (2)
C4	0.042 (3)	0.052 (3)	0.035 (3)	−0.010 (3)	0.007 (3)	0.002 (2)
C14	0.044 (3)	0.050 (3)	0.044 (3)	−0.004 (3)	0.007 (3)	0.007 (3)
C21	0.052 (4)	0.059 (4)	0.056 (4)	0.000 (3)	0.009 (3)	−0.004 (3)
C26	0.037 (3)	0.051 (3)	0.038 (3)	−0.003 (3)	0.004 (2)	0.005 (3)
C25	0.051 (4)	0.067 (4)	0.047 (3)	−0.004 (3)	0.009 (3)	0.001 (3)
C29	0.043 (3)	0.071 (4)	0.041 (3)	0.001 (3)	0.008 (3)	0.003 (3)
C23	0.049 (4)	0.065 (4)	0.057 (4)	−0.012 (3)	0.000 (3)	0.005 (3)
C19	0.048 (3)	0.046 (3)	0.045 (3)	0.003 (3)	0.007 (3)	0.005 (3)
C20	0.041 (3)	0.058 (3)	0.040 (3)	−0.003 (3)	0.003 (3)	0.010 (3)
C16	0.047 (4)	0.072 (4)	0.068 (4)	−0.018 (3)	0.004 (3)	0.001 (4)
C31	0.052 (4)	0.061 (4)	0.065 (4)	0.011 (3)	0.017 (3)	0.005 (3)
C18	0.048 (4)	0.054 (3)	0.061 (4)	0.004 (3)	0.024 (3)	0.007 (3)
C15	0.052 (4)	0.064 (4)	0.050 (4)	−0.011 (3)	0.010 (3)	−0.003 (3)
C7	0.049 (4)	0.068 (4)	0.041 (3)	−0.016 (3)	0.012 (3)	−0.005 (3)
C5	0.060 (4)	0.048 (3)	0.052 (4)	−0.004 (3)	0.002 (3)	−0.003 (3)
C30	0.070 (5)	0.074 (4)	0.058 (4)	0.003 (4)	0.031 (4)	0.020 (3)
C24	0.040 (3)	0.076 (4)	0.057 (4)	−0.003 (3)	0.008 (3)	0.004 (3)
C27	0.076 (5)	0.065 (4)	0.054 (4)	0.007 (4)	0.017 (3)	0.012 (3)
C6	0.062 (4)	0.060 (4)	0.046 (4)	−0.007 (3)	−0.002 (3)	0.004 (3)
C9	0.060 (4)	0.051 (4)	0.053 (4)	0.005 (3)	0.008 (3)	0.000 (3)
C28	0.059 (4)	0.075 (4)	0.063 (4)	0.013 (3)	0.020 (3)	−0.004 (4)
C17	0.047 (4)	0.062 (4)	0.068 (4)	−0.006 (3)	0.023 (3)	0.005 (3)
C8	0.070 (4)	0.054 (4)	0.065 (4)	−0.006 (3)	0.012 (4)	−0.017 (3)
C22	0.053 (4)	0.066 (4)	0.059 (4)	−0.003 (3)	0.004 (3)	−0.009 (3)
C10	0.064 (4)	0.099 (5)	0.058 (4)	−0.028 (4)	0.010 (4)	−0.026 (4)
C13	0.117 (8)	0.107 (7)	0.081 (6)	−0.015 (5)	−0.001 (5)	−0.043 (5)
C12	0.110 (8)	0.145 (9)	0.065 (5)	0.013 (6)	−0.028 (5)	−0.028 (6)
C11	0.091 (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)
O1	0.057 (3)	0.071 (3)	0.048 (2)	−0.012 (2)	0.011 (2)	−0.008 (2)

Geometric parameters (Å, º) top

Br2—C29	1.899 (6)	C18—C17	1.361 (9)
Br1—C23	1.891 (6)	C15—H15	0.9300
Cl1—C18	1.725 (6)	C7—C8	1.368 (10)
Cl2—C16	1.743 (6)	C7—C6	1.380 (9)
N1—C1	1.365 (7)	C7—C10	1.532 (9)
N1—C3	1.400 (7)	C5—C6	1.375 (9)
N1—C4	1.443 (7)	C5—H5	0.9300
C1—N2	1.321 (7)	C30—H30	0.9300
C1—C14	1.466 (8)	C24—H24	0.9300
N2—C2	1.383 (7)	C27—C28	1.386 (10)
C2—C3	1.369 (8)	C27—H27	0.9300
C2—C20	1.473 (8)	C6—H6	0.9300
C3—C26	1.462 (8)	C9—C8	1.359 (10)
C4—C5	1.364 (9)	C9—H9	0.9300
C4—C9	1.371 (8)	C28—H28	0.9300
C14—C15	1.388 (9)	C17—H17	0.9300
C14—C19	1.424 (8)	C8—H8	0.9300
C21—C22	1.385 (9)	C22—H22	0.9300
C21—C20	1.391 (9)	C10—C11'	1.44 (3)
C21—H21	0.9300	C10—C13	1.493 (12)
C26—C31	1.359 (9)	C10—C12	1.550 (14)
C26—C27	1.375 (9)	C10—C11	1.70 (3)
C25—C24	1.362 (9)	C13—H13A	0.9600
C25—C20	1.395 (9)	C13—H13B	0.9600
C25—H25	0.9300	C13—H13C	0.9600
C29—C30	1.338 (9)	C12—H12A	0.9600
C29—C28	1.362 (9)	C12—H12B	0.9600
C23—C24	1.387 (10)	C12—H12C	0.9600
C23—C22	1.393 (9)	C11—H11A	0.9600
C19—O1	1.323 (7)	C11—H11B	0.9600
C19—C18	1.410 (8)	C11—H11C	0.9600
C16—C17	1.339 (10)	C11'—H11D	0.9600
C16—C15	1.395 (9)	C11'—H11E	0.9600
C31—C30	1.373 (9)	C11'—H11F	0.9600
C31—H31	0.9300	O1—H1	0.8200

C1—N1—C3	107.6 (4)	C31—C30—H30	119.7
C1—N1—C4	129.4 (5)	C25—C24—C23	119.1 (6)
C3—N1—C4	122.8 (5)	C25—C24—H24	120.5
N2—C1—N1	110.4 (5)	C23—C24—H24	120.5
N2—C1—C14	121.9 (5)	C26—C27—C28	121.9 (6)
N1—C1—C14	127.5 (5)	C26—C27—H27	119.1
C1—N2—C2	106.9 (5)	C28—C27—H27	119.1
C3—C2—N2	109.9 (5)	C5—C6—C7	121.6 (6)
C3—C2—C20	129.8 (5)	C5—C6—H6	119.2
N2—C2—C20	120.2 (5)	C7—C6—H6	119.2
C2—C3—N1	105.2 (5)	C8—C9—C4	119.3 (6)
C2—C3—C26	132.9 (5)	C8—C9—H9	120.3
N1—C3—C26	121.9 (5)	C4—C9—H9	120.3
C5—C4—C9	119.9 (6)	C29—C28—C27	118.1 (6)
C5—C4—N1	119.6 (5)	C29—C28—H28	121.0
C9—C4—N1	120.5 (5)	C27—C28—H28	121.0
C15—C14—C19	119.0 (5)	C16—C17—C18	119.7 (6)
C15—C14—C1	124.0 (5)	C16—C17—H17	120.2
C19—C14—C1	117.0 (5)	C18—C17—H17	120.2
C22—C21—C20	121.2 (6)	C9—C8—C7	122.8 (6)
C22—C21—H21	119.4	C9—C8—H8	118.6
C20—C21—H21	119.4	C7—C8—H8	118.6
C31—C26—C27	117.5 (6)	C21—C22—C23	118.8 (6)
C31—C26—C3	121.4 (5)	C21—C22—H22	120.6
C27—C26—C3	121.1 (5)	C23—C22—H22	120.6
C24—C25—C20	122.0 (6)	C11'—C10—C13	115.5 (14)
C24—C25—H25	119.0	C11'—C10—C7	109.4 (13)
C20—C25—H25	119.0	C13—C10—C7	114.0 (7)
C30—C29—C28	120.9 (6)	C11'—C10—C12	96.7 (16)
C30—C29—Br2	120.8 (5)	C13—C10—C12	108.1 (7)
C28—C29—Br2	118.3 (5)	C7—C10—C12	111.9 (6)
C24—C23—C22	120.9 (6)	C13—C10—C11	99.7 (17)
C24—C23—Br1	119.8 (5)	C7—C10—C11	102.0 (13)
C22—C23—Br1	119.2 (5)	C12—C10—C11	120.7 (17)
O1—C19—C18	118.4 (5)	C10—C13—H13A	109.5
O1—C19—C14	124.1 (5)	C10—C13—H13B	109.5
C18—C19—C14	117.5 (5)	H13A—C13—H13B	109.5
C21—C20—C25	118.0 (5)	C10—C13—H13C	109.5
C21—C20—C2	120.1 (5)	H13A—C13—H13C	109.5
C25—C20—C2	121.9 (5)	H13B—C13—H13C	109.5
C17—C16—C15	121.8 (6)	C10—C12—H12A	109.5
C17—C16—Cl2	119.6 (5)	C10—C12—H12B	109.5
C15—C16—Cl2	118.5 (5)	H12A—C12—H12B	109.5
C26—C31—C30	121.1 (6)	C10—C12—H12C	109.5
C26—C31—H31	119.5	H12A—C12—H12C	109.5
C30—C31—H31	119.5	H12B—C12—H12C	109.5
C17—C18—C19	122.1 (6)	C10—C11—H11A	109.5
C17—C18—Cl1	120.1 (5)	C10—C11—H11B	109.5
C19—C18—Cl1	117.9 (5)	H11A—C11—H11B	109.5
C14—C15—C16	119.9 (6)	C10—C11—H11C	109.5
C14—C15—H15	120.1	H11A—C11—H11C	109.5
C16—C15—H15	120.1	H11B—C11—H11C	109.5
C8—C7—C6	116.7 (6)	C10—C11'—H11D	109.5
C8—C7—C10	122.2 (6)	C10—C11'—H11E	109.5
C6—C7—C10	121.0 (6)	H11D—C11'—H11E	109.5
C4—C5—C6	119.6 (6)	C10—C11'—H11F	109.5
C4—C5—H5	120.2	H11D—C11'—H11F	109.5
C6—C5—H5	120.2	H11E—C11'—H11F	109.5
C29—C30—C31	120.5 (6)	C19—O1—H1	109.5
C29—C30—H30	119.7

C3—N1—C1—N2	−1.0 (6)	C14—C19—C18—C17	2.4 (9)
C4—N1—C1—N2	173.7 (5)	O1—C19—C18—Cl1	−0.9 (7)
C3—N1—C1—C14	174.4 (5)	C14—C19—C18—Cl1	−178.7 (4)
C4—N1—C1—C14	−10.9 (9)	C19—C14—C15—C16	−0.4 (9)
N1—C1—N2—C2	1.3 (6)	C1—C14—C15—C16	−179.1 (6)
C14—C1—N2—C2	−174.4 (5)	C17—C16—C15—C14	0.1 (10)
C1—N2—C2—C3	−1.0 (6)	Cl2—C16—C15—C14	179.5 (5)
C1—N2—C2—C20	−178.2 (5)	C9—C4—C5—C6	−2.5 (9)
N2—C2—C3—N1	0.4 (6)	N1—C4—C5—C6	176.8 (5)
C20—C2—C3—N1	177.3 (5)	C28—C29—C30—C31	0.4 (11)
N2—C2—C3—C26	−176.0 (6)	Br2—C29—C30—C31	−177.7 (5)
C20—C2—C3—C26	0.8 (10)	C26—C31—C30—C29	1.1 (11)
C1—N1—C3—C2	0.4 (6)	C20—C25—C24—C23	0.3 (9)
C4—N1—C3—C2	−174.8 (5)	C22—C23—C24—C25	−1.8 (10)
C1—N1—C3—C26	177.3 (5)	Br1—C23—C24—C25	−179.2 (5)
C4—N1—C3—C26	2.1 (8)	C31—C26—C27—C28	1.8 (10)
C1—N1—C4—C5	−67.3 (8)	C3—C26—C27—C28	−178.3 (6)
C3—N1—C4—C5	106.7 (6)	C4—C5—C6—C7	0.4 (10)
C1—N1—C4—C9	112.0 (7)	C8—C7—C6—C5	2.0 (10)
C3—N1—C4—C9	−74.0 (7)	C10—C7—C6—C5	−173.7 (6)
N2—C1—C14—C15	170.8 (6)	C5—C4—C9—C8	2.2 (9)
N1—C1—C14—C15	−4.1 (9)	N1—C4—C9—C8	−177.2 (6)
N2—C1—C14—C19	−7.9 (8)	C30—C29—C28—C27	−0.8 (10)
N1—C1—C14—C19	177.2 (5)	Br2—C29—C28—C27	177.4 (5)
C2—C3—C26—C31	93.4 (8)	C26—C27—C28—C29	−0.4 (11)
N1—C3—C26—C31	−82.5 (7)	C15—C16—C17—C18	1.5 (10)
C2—C3—C26—C27	−86.5 (8)	Cl2—C16—C17—C18	−178.0 (5)
N1—C3—C26—C27	97.6 (7)	C19—C18—C17—C16	−2.8 (10)
C15—C14—C19—O1	−178.4 (5)	Cl1—C18—C17—C16	178.3 (5)
C1—C14—C19—O1	0.4 (8)	C4—C9—C8—C7	0.3 (10)
C15—C14—C19—C18	−0.8 (8)	C6—C7—C8—C9	−2.3 (10)
C1—C14—C19—C18	178.0 (5)	C10—C7—C8—C9	173.3 (7)
C22—C21—C20—C25	−0.1 (9)	C20—C21—C22—C23	−1.4 (10)
C22—C21—C20—C2	179.8 (6)	C24—C23—C22—C21	2.3 (10)
C24—C25—C20—C21	0.6 (9)	Br1—C23—C22—C21	179.7 (5)
C24—C25—C20—C2	−179.2 (5)	C8—C7—C10—C11'	−105.9 (17)
C3—C2—C20—C21	−150.0 (6)	C6—C7—C10—C11'	69.6 (17)
N2—C2—C20—C21	26.6 (8)	C8—C7—C10—C13	25.1 (10)
C3—C2—C20—C25	29.9 (9)	C6—C7—C10—C13	−159.5 (7)
N2—C2—C20—C25	−153.5 (5)	C8—C7—C10—C12	148.2 (7)
C27—C26—C31—C30	−2.2 (10)	C6—C7—C10—C12	−36.3 (9)
C3—C26—C31—C30	177.9 (6)	C8—C7—C10—C11	−81.4 (18)
O1—C19—C18—C17	−179.9 (6)	C6—C7—C10—C11	94.0 (18)

Hydrogen-bond geometry (Å, º) top

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

D—H···A	D—H	H···A	D···A	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+3/2, y+5/2, z.

References

Brown, E. G. (1998). Ring Nitrogen and Key Biomolecules, ch. 2. Boston: Kluwer Academic Publishers. Google Scholar
Bruker. (1998). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Forte, B., Malgesini, B., Piutti, C., Quartieri, F., Scolaro, A. & Papeo, G. A. (2009). Marine Drugs, 7, 705–753. CrossRef CAS PubMed Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Watkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON. Chemical Crystallography Laboratory, University of Oxford, England. Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

IUCrDATA

ISSN: 2414-3146

Volume 4| Part 12| December 2019| x191672

https://doi.org/10.1107/S2414314619016729

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text
		Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text
		Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

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

Structure description

Synthesis and crystallization

Refinement

Structural data

References

organic compounds

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