2-(5-Bromo­thio­phen-2-yl)-1-phenyl-1H-phenanthro[9,10-d]imidazole

Kavitha, T.; Mayakrishnan, S.; Perumal, T.P.; Suvasini, C.; Lakshmi, S.

doi:10.1107/S241431461700089X

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 1| January 2017| x170089

https://doi.org/10.1107/S241431461700089X

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2-(5-Bromothiophen-2-yl)-1-phenyl-1H-phenanthro[9,10-d]imidazole

T. Kavitha,^a Sivakalai Mayakrishnan,^b T. Paramasivam Perumal,^b Chandramouleeswaran Suvasini ^a and Srinivasakannan Lakshmi ^a ^*

^aResearch Department of Physics, S.D.N.B. Vaishnav College for Women, Chrompet, Chennai 600 044, India, and ^bOrganic & Bioorganic Chemistry, CSIR–Central Leather Research Institute, Adyar, Chennai 600 020, India
^*Correspondence e-mail: lakssdnbvc@gmail.com

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 8 January 2017; accepted 18 January 2017; online 20 January 2017)

In the title molecule, C₂₅H₁₅BrN₂S, the phenanthrene system is slightly skewed, with a dihedral angle of 8.94 (16)° between the outer benzene rings. The imidazole ring makes dihedral angles of 15.18 (16), 2.94 (15) and 88.46 (16)°, respectively, with the thiophene ring, the central benzene ring of the phenanthrene unit and the phenyl ring attached to the latter unit. In the molecule, there are two C—H⋯π interactions present involving the phenyl ring. In the crystal, molecules are linked by C—H⋯N and C—H⋯Br hydrogen bonds, forming zigzag chains along the a axis. The chains are linked by C—H⋯π interactions, forming a three-dimensional supramolecular structure.

Keywords: crystal structure; phenanthrene; imidazole; thiophene; C—H⋯N and C—H⋯Br hydrogen bonding; C—H⋯π interactions.

CCDC reference: 1528232

Structure description

1H-Phenathro[9,10-d]imidazole derivatives act as multi-functional agents for the treatment of Alzheimer's disease (Liu et al., 2014 ). This unit has been identified as an excellent building block for tuning carrier injection properties as well as blue emission (Wang et al., 2011 ). Imidazole derivatives are found to have diverse activities, such as anti-inflammatory, antimicrobial (Divya et al., 2013 ), antibacterial, anticancer, antifungal, analgesic, anti-HIV and antituberculosis (Verma et al., 2013 ). The presence of a 5-bromothiophen-2-yl unit is found to enhance the antibacterial activity of piperazinyl quinolones (Foroumadi et al., 2005 ) and antimicrobial activity in pyrazoline derivatives (Sasikala et al., 2012 ).

In the title compound, illustrated in Fig. 1, the phenanthrene ring system is slightly skewed with a dihedral angle of 8.94 (16)° between the outer benzene rings. The imidazole ring makes dihedral angles of 15.18 (16), 2.94 (15) and 88.46 (16)°, respectively, with the thiophene ring, the central benzene ring (C6–C8/C13/C14/C19) of the phenanthrene unit, and the phenyl ring (C20–C25). In the molecule, there are two C—H⋯π interactions present involving the phenyl ring (Table 1 and Fig. 1).

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C20–C25 and C8–C13 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C21—H21⋯N1ⁱ	0.93	2.44	3.317 (4)	157
C25—H25⋯Br1ⁱⁱ	0.93	2.93	3.828 (3)	164
C3—H3⋯Cg1	0.93	2.99	3.716 (3)	136
C9—H9⋯Cg1	0.93	2.94	3.789 (3)	153
C15—H15⋯Cg2ⁱⁱⁱ	0.93	2.90	3.580 (4)	131
Symmetry codes: (i) -x-1, -y, -z+2; (ii) -x, -y, -z+2; (iii) $[x-{\script{1\over 2}}, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Figure 1
The molecular structure of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 30% probability level. The C—H⋯π interactions are shown as blue dashed arrows (see Table 1

In the crystal, molecules are linked by C—H⋯N and C—H⋯Br hydrogen bonds forming zigzag chains propagating along the a-axis direction (Table 1 and Fig. 2). The chains are linked by C—H⋯π interactions, forming a three-dimensional supramolecular structure (Table 1 and Fig. 3).

Figure 2
A partial view along the c axis, of the crystal packing of the title compound. The hydrogen bonds are shown as blue lines (see Table 1

Figure 3
A view along the c axis, of the crystal packing of the title compound. The hydrogen bonds and C—H⋯π interactions are shown as dashed lines (see Table 1

). For clarity, only the H atoms involved in these interactions have been included.

Synthesis and crystallization

9,10-Phenanthrenequinone (1 equiv.), aniline (1.2 equiv.), 5-bromothiophene-2-carbaldehyde (1.5 equiv.) and ammonium acetate (3.0 equiv.) in glacial acetic acid (10 ml) were refluxed for 24 h under a nitrogen atmosphere. After cooling to room temperature, the dark-yellow mixture was poured into a methanol solution with stirring. The separated solid was filtered off, washed with methanol and dried to give a white solid. A yellow powder was finally obtained after it was stirred in refluxing ethanol, subsequently filtered and dried in vacuum, yielding 2-(5-bromothiophen-2-yl)-1-phenyl-1H-phenanthro[9,10-d]imidazole. Finally, the title compound was crystallized from dimethyl sulfoxide, giving colourless block-like crystals on evaporation of the solvent.

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula	C₂₅H₁₅BrN₂S
M_r	455.36
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	9.2966 (4), 23.0723 (11), 9.8089 (4)
β (°)	109.663 (1)
V (Å³)	1981.26 (15)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	2.19
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2004 )
T_min, T_max	0.566, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	38101, 3481, 2628
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.098, 1.04
No. of reflections	3481
No. of parameters	262
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.53
Computer programs: APEX2 and SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008 ), SHELXL2016 (Sheldrick, 2015 ), ORTEP-3 for Windows (Farrugia, 2012 ), Mercury (Macrae et al., 2008 ), PLATON (Spek, 2009 ) and publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 1528232

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S241431461700089X/su4124sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S241431461700089X/su4124Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S241431461700089X/su4124Isup3.cml

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012), Mercury (Macrae et al., 2008) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2016 (Sheldrick, 2015), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

2-(5-Bromothiophen-2-yl)-1-phenyl-1H-phenanthro[9,10-d]imidazole top

Crystal data top

C₂₅H₁₅BrN₂S	F(000) = 920
M_r = 455.36	D_x = 1.527 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.2966 (4) Å	Cell parameters from 5918 reflections
b = 23.0723 (11) Å	θ = 4.4–47.5°
c = 9.8089 (4) Å	µ = 2.19 mm⁻¹
β = 109.663 (1)°	T = 296 K
V = 1981.26 (15) Å³	Block, colourless
Z = 4	0.30 × 0.25 × 0.20 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	2628 reflections with I > 2σ(I)
Bruker Kappa AXEXII CCD scans	R_int = 0.037
Absorption correction: multi-scan (SADABS; Bruker, 2004)	θ_max = 25.0°, θ_min = 1.8°
T_min = 0.566, T_max = 0.746	h = −10→11
38101 measured reflections	k = −27→27
3481 independent reflections	l = −11→11

Refinement top

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.098	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0479P)² + 1.1409P] where P = (F_o² + 2F_c²)/3
3481 reflections	(Δ/σ)_max = 0.007
262 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	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
C24	−0.0791 (4)	−0.08057 (17)	1.4777 (3)	0.0664 (10)
H24	0.015529	−0.096518	1.528863	0.080*
BR1	−0.00847 (5)	0.17241 (2)	0.93171 (4)	0.07188 (17)
S2	−0.16978 (10)	0.05218 (3)	0.89706 (8)	0.0538 (2)
N2	−0.3378 (2)	−0.06860 (10)	1.0994 (2)	0.0410 (5)
C1	−0.0987 (3)	0.11209 (12)	1.0013 (3)	0.0475 (7)
N1	−0.3613 (3)	−0.05272 (10)	0.8668 (2)	0.0442 (6)
C20	−0.2781 (3)	−0.06280 (11)	1.2546 (3)	0.0404 (6)
C6	−0.4345 (3)	−0.10315 (11)	0.8778 (3)	0.0411 (6)
C8	−0.4921 (3)	−0.16417 (12)	1.0589 (3)	0.0418 (7)
C5	−0.3052 (3)	−0.03288 (12)	1.0006 (3)	0.0418 (6)
C13	−0.5749 (3)	−0.20196 (12)	0.9446 (3)	0.0432 (7)
C7	−0.4228 (3)	−0.11464 (11)	1.0187 (3)	0.0396 (6)
C4	−0.2256 (3)	0.02220 (12)	1.0335 (3)	0.0410 (6)
C19	−0.5249 (3)	−0.13826 (12)	0.7599 (3)	0.0426 (7)
C9	−0.4840 (4)	−0.17749 (12)	1.2015 (3)	0.0492 (7)
H9	−0.432874	−0.152529	1.276629	0.059*
C2	−0.1179 (3)	0.10985 (13)	1.1311 (3)	0.0499 (7)
H2	−0.087128	0.138927	1.200569	0.060*
C14	−0.5959 (3)	−0.18781 (12)	0.7933 (3)	0.0429 (7)
C21	−0.3609 (3)	−0.03426 (13)	1.3267 (3)	0.0484 (7)
H21	−0.456502	−0.018883	1.276119	0.058*
C18	−0.5507 (3)	−0.12308 (13)	0.6154 (3)	0.0522 (7)
H18	−0.500921	−0.091129	0.594274	0.063*
C3	−0.1900 (3)	0.05827 (13)	1.1492 (3)	0.0498 (7)
H3	−0.211301	0.049664	1.233028	0.060*
C12	−0.6381 (4)	−0.25200 (13)	0.9816 (4)	0.0558 (8)
H12	−0.689606	−0.277845	0.908785	0.067*
C25	−0.1370 (3)	−0.08590 (14)	1.3285 (3)	0.0540 (8)
H25	−0.081184	−0.104828	1.279000	0.065*
C17	−0.6483 (4)	−0.15479 (14)	0.5052 (3)	0.0583 (8)
H17	−0.667786	−0.143578	0.409577	0.070*
C10	−0.5507 (4)	−0.22676 (14)	1.2310 (4)	0.0578 (8)
H10	−0.544689	−0.235002	1.325530	0.069*
C15	−0.6928 (4)	−0.21939 (14)	0.6760 (3)	0.0548 (8)
H15	−0.741404	−0.252239	0.694186	0.066*
C22	−0.2998 (4)	−0.02878 (14)	1.4756 (3)	0.0536 (8)
H22	−0.354303	−0.009112	1.525202	0.064*
C11	−0.6266 (4)	−0.26412 (14)	1.1203 (4)	0.0630 (9)
H11	−0.670272	−0.297820	1.140891	0.076*
C23	−0.1604 (4)	−0.05193 (15)	1.5505 (3)	0.0600 (9)
H23	−0.120647	−0.048303	1.650726	0.072*
C16	−0.7178 (4)	−0.20332 (15)	0.5359 (3)	0.0608 (9)
H16	−0.782361	−0.225350	0.460634	0.073*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C24	0.059 (2)	0.087 (3)	0.0433 (19)	0.0244 (19)	0.0035 (16)	−0.0002 (17)
BR1	0.1031 (3)	0.0497 (2)	0.0836 (3)	−0.01989 (18)	0.0588 (2)	−0.01601 (17)
S2	0.0765 (6)	0.0446 (4)	0.0456 (4)	−0.0110 (4)	0.0274 (4)	−0.0082 (3)
N2	0.0465 (13)	0.0412 (13)	0.0323 (12)	−0.0010 (10)	0.0091 (10)	0.0014 (10)
C1	0.0513 (17)	0.0407 (16)	0.0529 (18)	−0.0024 (13)	0.0207 (14)	−0.0059 (13)
N1	0.0505 (13)	0.0432 (13)	0.0356 (13)	−0.0054 (11)	0.0103 (11)	−0.0002 (10)
C20	0.0459 (16)	0.0388 (15)	0.0338 (15)	−0.0002 (12)	0.0098 (13)	0.0017 (11)
C6	0.0447 (16)	0.0376 (15)	0.0400 (16)	0.0003 (12)	0.0130 (13)	0.0007 (12)
C8	0.0417 (15)	0.0414 (16)	0.0432 (16)	0.0082 (12)	0.0156 (13)	0.0035 (12)
C5	0.0446 (15)	0.0412 (15)	0.0363 (16)	0.0028 (12)	0.0090 (13)	0.0029 (12)
C13	0.0438 (16)	0.0367 (15)	0.0501 (18)	0.0041 (12)	0.0170 (13)	0.0003 (13)
C7	0.0417 (15)	0.0375 (15)	0.0377 (15)	0.0059 (12)	0.0108 (12)	0.0006 (12)
C4	0.0430 (15)	0.0436 (15)	0.0333 (15)	0.0024 (12)	0.0087 (12)	0.0009 (12)
C19	0.0467 (16)	0.0411 (16)	0.0403 (16)	0.0022 (12)	0.0147 (13)	−0.0024 (12)
C9	0.0618 (19)	0.0431 (17)	0.0454 (18)	0.0076 (14)	0.0214 (15)	0.0056 (13)
C2	0.0569 (18)	0.0435 (16)	0.0478 (18)	−0.0058 (14)	0.0154 (15)	−0.0119 (14)
C14	0.0424 (15)	0.0418 (15)	0.0468 (17)	0.0041 (12)	0.0179 (13)	−0.0043 (13)
C21	0.0454 (16)	0.0545 (18)	0.0445 (17)	0.0099 (14)	0.0140 (14)	0.0053 (14)
C18	0.0617 (19)	0.0497 (18)	0.0464 (18)	−0.0052 (15)	0.0200 (15)	−0.0035 (14)
C3	0.0543 (18)	0.0558 (18)	0.0386 (17)	−0.0044 (14)	0.0150 (14)	−0.0025 (14)
C12	0.062 (2)	0.0440 (17)	0.061 (2)	−0.0049 (15)	0.0193 (16)	0.0027 (15)
C25	0.0552 (18)	0.062 (2)	0.0440 (18)	0.0158 (15)	0.0154 (15)	−0.0030 (15)
C17	0.072 (2)	0.062 (2)	0.0424 (18)	−0.0024 (17)	0.0209 (16)	−0.0116 (15)
C10	0.071 (2)	0.0533 (19)	0.056 (2)	0.0093 (16)	0.0302 (17)	0.0149 (16)
C15	0.0569 (19)	0.0488 (18)	0.064 (2)	−0.0123 (15)	0.0265 (16)	−0.0134 (15)
C22	0.064 (2)	0.0571 (19)	0.0458 (18)	0.0046 (16)	0.0258 (16)	−0.0014 (15)
C11	0.072 (2)	0.0482 (19)	0.076 (2)	−0.0021 (17)	0.0337 (19)	0.0145 (18)
C23	0.066 (2)	0.072 (2)	0.0368 (17)	0.0058 (18)	0.0105 (16)	−0.0017 (15)
C16	0.070 (2)	0.066 (2)	0.0446 (19)	−0.0132 (18)	0.0172 (16)	−0.0212 (16)

Geometric parameters (Å, º) top

C24—C23	1.372 (5)	C9—C10	1.371 (4)
C24—C25	1.384 (4)	C9—H9	0.9300
C24—H24	0.9300	C2—C3	1.406 (4)
BR1—C1	1.869 (3)	C2—H2	0.9300
S2—C1	1.714 (3)	C14—C15	1.403 (4)
S2—C4	1.733 (3)	C21—C22	1.383 (4)
N2—C5	1.381 (3)	C21—H21	0.9300
N2—C7	1.399 (3)	C18—C17	1.367 (4)
N2—C20	1.441 (3)	C18—H18	0.9300
C1—C2	1.345 (4)	C3—H3	0.9300
N1—C5	1.320 (3)	C12—C11	1.358 (5)
N1—C6	1.370 (3)	C12—H12	0.9300
C20—C25	1.376 (4)	C25—H25	0.9300
C20—C21	1.376 (4)	C17—C16	1.376 (5)
C6—C7	1.375 (4)	C17—H17	0.9300
C6—C19	1.430 (4)	C10—C11	1.380 (5)
C8—C9	1.409 (4)	C10—H10	0.9300
C8—C13	1.425 (4)	C15—C16	1.366 (4)
C8—C7	1.431 (4)	C15—H15	0.9300
C5—C4	1.451 (4)	C22—C23	1.366 (4)
C13—C12	1.397 (4)	C22—H22	0.9300
C13—C14	1.468 (4)	C11—H11	0.9300
C4—C3	1.356 (4)	C23—H23	0.9300
C19—C18	1.400 (4)	C16—H16	0.9300
C19—C14	1.413 (4)

C23—C24—C25	120.5 (3)	C3—C2—H2	124.1
C23—C24—H24	119.7	C15—C14—C19	116.8 (3)
C25—C24—H24	119.7	C15—C14—C13	123.0 (3)
C1—S2—C4	90.96 (14)	C19—C14—C13	120.1 (2)
C5—N2—C7	105.8 (2)	C20—C21—C22	119.0 (3)
C5—N2—C20	126.0 (2)	C20—C21—H21	120.5
C7—N2—C20	127.7 (2)	C22—C21—H21	120.5
C2—C1—S2	112.7 (2)	C17—C18—C19	120.6 (3)
C2—C1—BR1	126.4 (2)	C17—C18—H18	119.7
S2—C1—BR1	120.87 (17)	C19—C18—H18	119.7
C5—N1—C6	104.9 (2)	C4—C3—C2	114.0 (3)
C25—C20—C21	121.0 (3)	C4—C3—H3	123.0
C25—C20—N2	118.7 (3)	C2—C3—H3	123.0
C21—C20—N2	120.3 (2)	C11—C12—C13	122.1 (3)
N1—C6—C7	111.7 (2)	C11—C12—H12	118.9
N1—C6—C19	126.1 (2)	C13—C12—H12	118.9
C7—C6—C19	122.0 (3)	C20—C25—C24	119.0 (3)
C9—C8—C13	118.8 (3)	C20—C25—H25	120.5
C9—C8—C7	124.7 (3)	C24—C25—H25	120.5
C13—C8—C7	116.5 (2)	C18—C17—C16	119.9 (3)
N1—C5—N2	112.6 (2)	C18—C17—H17	120.1
N1—C5—C4	121.7 (2)	C16—C17—H17	120.1
N2—C5—C4	125.7 (2)	C9—C10—C11	120.0 (3)
C12—C13—C8	117.7 (3)	C9—C10—H10	120.0
C12—C13—C14	121.4 (3)	C11—C10—H10	120.0
C8—C13—C14	120.8 (3)	C16—C15—C14	122.0 (3)
C6—C7—N2	105.1 (2)	C16—C15—H15	119.0
C6—C7—C8	122.7 (2)	C14—C15—H15	119.0
N2—C7—C8	132.1 (2)	C23—C22—C21	120.7 (3)
C3—C4—C5	133.3 (3)	C23—C22—H22	119.6
C3—C4—S2	110.4 (2)	C21—C22—H22	119.6
C5—C4—S2	116.2 (2)	C12—C11—C10	120.4 (3)
C18—C19—C14	120.2 (3)	C12—C11—H11	119.8
C18—C19—C6	122.1 (3)	C10—C11—H11	119.8
C14—C19—C6	117.7 (3)	C22—C23—C24	119.8 (3)
C10—C9—C8	120.9 (3)	C22—C23—H23	120.1
C10—C9—H9	119.6	C24—C23—H23	120.1
C8—C9—H9	119.6	C15—C16—C17	120.5 (3)
C1—C2—C3	111.9 (3)	C15—C16—H16	119.7
C1—C2—H2	124.1	C17—C16—H16	119.7

C4—S2—C1—C2	−0.7 (2)	N1—C6—C19—C14	−177.7 (3)
C4—S2—C1—BR1	179.99 (18)	C7—C6—C19—C14	−3.6 (4)
C5—N2—C20—C25	−83.7 (4)	C13—C8—C9—C10	1.9 (4)
C7—N2—C20—C25	87.2 (3)	C7—C8—C9—C10	−178.3 (3)
C5—N2—C20—C21	95.8 (3)	S2—C1—C2—C3	0.8 (3)
C7—N2—C20—C21	−93.2 (3)	BR1—C1—C2—C3	180.0 (2)
C5—N1—C6—C7	−0.4 (3)	C18—C19—C14—C15	−0.9 (4)
C5—N1—C6—C19	174.3 (3)	C6—C19—C14—C15	175.6 (3)
C6—N1—C5—N2	0.4 (3)	C18—C19—C14—C13	−176.9 (3)
C6—N1—C5—C4	−176.6 (2)	C6—C19—C14—C13	−0.4 (4)
C7—N2—C5—N1	−0.3 (3)	C12—C13—C14—C15	7.1 (4)
C20—N2—C5—N1	172.2 (2)	C8—C13—C14—C15	−171.4 (3)
C7—N2—C5—C4	176.6 (3)	C12—C13—C14—C19	−177.1 (3)
C20—N2—C5—C4	−10.9 (4)	C8—C13—C14—C19	4.4 (4)
C9—C8—C13—C12	−2.9 (4)	C25—C20—C21—C22	0.3 (4)
C7—C8—C13—C12	177.2 (2)	N2—C20—C21—C22	−179.2 (3)
C9—C8—C13—C14	175.6 (3)	C14—C19—C18—C17	2.1 (4)
C7—C8—C13—C14	−4.3 (4)	C6—C19—C18—C17	−174.2 (3)
N1—C6—C7—N2	0.2 (3)	C5—C4—C3—C2	−176.5 (3)
C19—C6—C7—N2	−174.7 (2)	S2—C4—C3—C2	−0.2 (3)
N1—C6—C7—C8	178.7 (2)	C1—C2—C3—C4	−0.4 (4)
C19—C6—C7—C8	3.8 (4)	C8—C13—C12—C11	2.1 (4)
C5—N2—C7—C6	0.1 (3)	C14—C13—C12—C11	−176.4 (3)
C20—N2—C7—C6	−172.3 (2)	C21—C20—C25—C24	0.6 (5)
C5—N2—C7—C8	−178.2 (3)	N2—C20—C25—C24	−179.9 (3)
C20—N2—C7—C8	9.4 (4)	C23—C24—C25—C20	−0.9 (5)
C9—C8—C7—C6	−179.5 (3)	C19—C18—C17—C16	−2.4 (5)
C13—C8—C7—C6	0.3 (4)	C8—C9—C10—C11	0.1 (5)
C9—C8—C7—N2	−1.5 (5)	C19—C14—C15—C16	0.0 (4)
C13—C8—C7—N2	178.3 (3)	C13—C14—C15—C16	175.9 (3)
N1—C5—C4—C3	161.8 (3)	C20—C21—C22—C23	−0.9 (5)
N2—C5—C4—C3	−14.9 (5)	C13—C12—C11—C10	−0.1 (5)
N1—C5—C4—S2	−14.3 (4)	C9—C10—C11—C12	−1.0 (5)
N2—C5—C4—S2	169.0 (2)	C21—C22—C23—C24	0.5 (5)
C1—S2—C4—C3	0.5 (2)	C25—C24—C23—C22	0.4 (6)
C1—S2—C4—C5	177.5 (2)	C14—C15—C16—C17	−0.3 (5)
N1—C6—C19—C18	−1.4 (4)	C18—C17—C16—C15	1.5 (5)
C7—C6—C19—C18	172.8 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C20–C25 and C8–C13 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21···N1ⁱ	0.93	2.44	3.317 (4)	157
C25—H25···Br1ⁱⁱ	0.93	2.93	3.828 (3)	164
C3—H3···Cg1	0.93	2.99	3.716 (3)	136
C9—H9···Cg1	0.93	2.94	3.789 (3)	153
C15—H15···Cg2ⁱⁱⁱ	0.93	2.90	3.580 (4)	131

Symmetry codes: (i) −x−1, −y, −z+2; (ii) −x, −y, −z+2; (iii) x−1/2, −y−1/2, z−1/2.

Acknowledgements

The authors thank the single-crystal XRD facility, SAIF IIT Madras, Chennai, for the data collection.

References

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Volume 2| Part 1| January 2017| x170089

https://doi.org/10.1107/S241431461700089X

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

2-(5-Bromo­thio­phen-2-yl)-1-phenyl-1H-phenanthro[9,10-d]imidazole

Structure description

Synthesis and crystallization

Refinement

Structural data

Acknowledgements

References

organic compounds

2-(5-Bromothiophen-2-yl)-1-phenyl-1H-phenanthro[9,10-d]imidazole