9-(4-Meth­oxy­phen­yl)-9H-carbazole

Ganesan, P.; Jasmine, N.J.; Darious, R.S.; Soundararajan, K.; Rajalingam, R.

doi:10.1107/S2414314623006740

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 8| Part 8| August 2023| x230674

https://doi.org/10.1107/S2414314623006740

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9-(4-Methoxyphenyl)-9H-carbazole

Prabhu Ganesan,^a Nithianantham Jeeva Jasmine,^b Robert Swinton Darious,^c Krishnan Soundararajan ^d and Renganathan Rajalingam ^a ^*

^aSchool of Chemistry, Bharathidasan University, Tiruchirappalli-620 024, Tamil Nadu, India, ^bMolecular Biophysics Unit, Indian Institute of Science, Bangalore, India, ^cPG & Research Department of Chemistry, Bishop Heber College (Autonomous), Tiruchirappalli-620 017, Tamil Nadu, India, and ^dDepartment of Chemistry, Periyar Maniammai Institute of Science and Technology, Vallam-613403, Thanjavur, Tamil Nadu, India
^*Correspondence e-mail: rrengas@gmail.com

Edited by W. T. A. Harrison, University of Aberdeen, United Kingdom (Received 28 July 2023; accepted 1 August 2023; online 10 August 2023)

In the title compound, C₁₉H₁₅NO, the dihedral angle between the benzene rings of the carbazole moiety is 1.73 (12)° and the methoxy-substituted phenyl ring deviates from the mean plane of the carbazole grouping (r.m.s. deviation = 0.020 Å) by 56.78 (8)°. In the crystal, weak C—H⋯π interactions link the molecules. The two-dimensional fingerprint plots derived from the Hirshfeld surface indicate that H⋯H (51.2%) and C⋯H/H⋯C (39.9%) contacts dominate the packing.

Keywords: carbazole; dihedral angle; torsion angle; Hirshfeld surface analysis; crystal structure.

CCDC reference: 2280833

Structure description

Carbazole and its derivatives have attracted attention in the development of electrical and electronic materials because of their conjugated π-electron systems (Taranekar et al., 2007 ). The N-heterocyclic carbazole molecule has also been employed as a promising candidate in the treatment of cancer (Patil et al., 2022 ). As part of our studies in this area, we now describe the synthesis and structure of the title compound.

The title compound crystallizes in the orthorhombic space group Pbca with one molecule in the asymmetric unit (Fig. 1). As expected, the C1–C12/N1 carbazole-fused-ring moiety is almost planar (Moreno-Fuquen et al., 2012 ) with a dihedral angle of 1.73 (12)° between the C1–C6 and C7–C12 rings. The dihedral angle between the C1–C12/N1 carbazole mean plane and the pendant C13–C18 ring is 56.78 (8)°. Atom C19 of the para-methoxy group deviates by 0.219 (3) Å from its attached ring. The crystal structure is consolidated by weak C—H⋯π interactions (Fig. 2) [C9—H9⋯Cg(N1/C1/C6–C8) = 2.71 Å; symmetry code: 1 − x, − $[{1\over 2}]$ + y, $[{3\over 2}]$ − z; C17—H17⋯Cg(C7–C12) = 2.92 Å; symmetry code: x, 1 + y, z]. The crystal packing viewed along the a-axis direction is shown in Fig. 3.

Figure 1
The molecular structure of the title compound, showing displacement ellipsoids drawn at the 30% probability level.

Figure 2
A view of the C—H⋯π interactions in the title compound. Cg1 is the centroid of the pyrrole ring of the carbazole molecule (symmetry code: 1 − x, − $[{1\over 2}]$ + y, $[{3\over 2}]$ − z) and Cg3 is the centroid of the phenyl ring of the carbazole molecule (symmetry code: x, 1 + y, z).

Figure 3
Crystal packing viewed along the a-axis direction.

The Hirshfeld surface and its related two-dimensional fingerprint plots (Spackman & Jayatilaka, 2009 ) were generated with Crystal Explorer 17.5 (Turner et al., 2017 ). The Hirshfeld surface mapped over d_norm within the range −0.05 to 1.63 a.u. shows a few red spots in the locales of D⋯A (D = donor, A = acceptor) interactions, consistent with the presence of weak C—H⋯π interactions (Fig. 4). The two-dimensional fingerprint plots (Fig. 5) show that H⋯H (51.2%) and C⋯H/H⋯C (39.9%) contacts dominate the packing with other contacts [C⋯C (0.7%), N⋯H/H⋯N (1.9%), O⋯C/C⋯O (0.3%), O⋯H/H⋯O (6.0%)] making minor contributions.

Figure 4
A view of the three-dimensional Hirshfeld surface of the title compound mapped over d_norm in the range −0.05 to 1.63 a.u.

Figure 5
The two-dimensional fingerprint plots (a–g) showing all intermolecular interactions and delineated into C⋯H/H⋯C, C⋯C, N⋯H/H⋯N, O⋯C/C⋯O, O—H⋯H⋯O and H⋯H contacts.

Synthesis and crystallization

A 100 ml round-bottom flask was charged with 4-iodoanisole 1.78 g (7.6 mmol, 1 equiv), 9H-carbazole 1.143 g (6.8 mmol, 1.1 equiv), which were uniformly dispersed in 35 ml of dimethylformamide (DMF) and the mixture was dissolved homogeneously under an N₂ atm. To the mixture, K₂CO₃ (5.25 g, 38 mmol, 5 equiv), CuI (0.144 g, 0.76 mmol, 0.1 equiv) and 1,10-phenanthroline (0.137 g, 0.76 mmol, 0.1 equiv) was added and the mixture was refluxed for 12 h under N₂. The progress of the reaction was monitored by TLC. After the completion of the reaction, the reaction was quenched in ice–water and the solid product was dissolved in ethyl acetate and washed with brine solution. The obtained solvent was removed under reduced pressure and the obtained residue was further purified using column chromatography (100–200 mesh silica gel) to afford the title compound as shown in Fig. 6. Single crystals in the form of colourless needles were grown from dichloromethane solution at room temperature.

Figure 6
Reaction scheme.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1.

Table 1
Experimental details

Crystal data
Chemical formula	C₁₉H₁₅NO
M_r	273.32
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	300
a, b, c (Å)	16.2645 (16), 7.8297 (7), 22.819 (2)
V (Å³)	2905.9 (5)
Z	8
Radiation type	Mo Kα
μ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.09 × 0.07

Data collection
Diffractometer	Bruker D8 CCD
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.665, 0.745
No. of measured, independent and observed [I > 2σ(I)] reflections	23109, 2762, 1564
R_int	0.062
(sin θ/λ)_max (Å⁻¹)	0.610

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.136, 1.08
No. of reflections	2762
No. of parameters	192
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.16
Computer programs: APEX4 and SAINT (Bruker, 2016 ), SHELXT (Sheldrick, 2015a ), SHELXL2019/1 (Sheldrick, 2015b ) and SHELXTL (Sheldrick, 2008 ).

Structural data

CCDC reference: 2280833

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314623006740/hb4441sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314623006740/hb4441Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314623006740/hb4441Isup3.cml

checkCIF report

Computing details top

Data collection: APEX4 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2019/1 (Sheldrick, 2015b); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

9-(4-Methoxyphenyl)-9H-carbazole top

Crystal data top

C₁₉H₁₅NO	D_x = 1.249 Mg m⁻³
M_r = 273.32	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 4004 reflections
a = 16.2645 (16) Å	θ = 2.5–21.3°
b = 7.8297 (7) Å	µ = 0.08 mm⁻¹
c = 22.819 (2) Å	T = 300 K
V = 2905.9 (5) Å³	Needle, colourless
Z = 8	0.30 × 0.09 × 0.07 mm
F(000) = 1152

Data collection top

Bruker D8 CCD diffractometer	1564 reflections with I > 2σ(I)
Radiation source: i-mu-s microfocus source	R_int = 0.062
φ and ω scans	θ_max = 25.7°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −17→19
T_min = 0.665, T_max = 0.745	k = −9→8
23109 measured reflections	l = −27→27
2762 independent reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.046	w = 1/[σ²(F_o²) + (0.0466P)² + 0.7157P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.136	(Δ/σ)_max < 0.001
S = 1.08	Δρ_max = 0.16 e Å⁻³
2762 reflections	Δρ_min = −0.16 e Å⁻³
192 parameters	Extinction correction: SHELXL2019/1 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0059 (8)
Primary atom site location: dual

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
O1	0.65084 (10)	0.6420 (2)	0.51323 (7)	0.0716 (5)
N1	0.53757 (11)	0.0699 (2)	0.63305 (7)	0.0556 (5)
C1	0.46058 (13)	−0.0072 (3)	0.62775 (9)	0.0549 (6)
C2	0.39388 (14)	0.0412 (3)	0.59364 (10)	0.0635 (6)
H2	0.395977	0.137531	0.569851	0.076*
C3	0.32440 (16)	−0.0593 (4)	0.59644 (11)	0.0751 (7)
H3	0.278853	−0.030830	0.573819	0.090*
C4	0.32109 (18)	−0.2021 (4)	0.63231 (12)	0.0824 (8)
H4	0.273344	−0.267428	0.633199	0.099*
C5	0.38662 (17)	−0.2493 (3)	0.66653 (11)	0.0738 (7)
H5	0.383598	−0.345344	0.690406	0.089*
C6	0.45791 (14)	−0.1502 (3)	0.66481 (9)	0.0576 (6)
C7	0.53597 (14)	−0.1588 (3)	0.69436 (9)	0.0570 (6)
C8	0.58357 (14)	−0.0225 (3)	0.67375 (9)	0.0546 (6)
C9	0.56892 (18)	−0.2696 (3)	0.73589 (10)	0.0705 (7)
H9	0.537681	−0.359282	0.750651	0.085*
C10	0.64787 (19)	−0.2448 (4)	0.75469 (11)	0.0795 (8)
H10	0.670210	−0.317769	0.782615	0.095*
C11	0.69510 (16)	−0.1116 (3)	0.73253 (11)	0.0746 (7)
H11	0.748920	−0.098279	0.745508	0.089*
C12	0.66401 (14)	0.0014 (3)	0.69172 (10)	0.0638 (6)
H12	0.695869	0.090072	0.676892	0.077*
C13	0.56442 (12)	0.2203 (3)	0.60315 (9)	0.0516 (6)
C14	0.56432 (13)	0.2272 (3)	0.54252 (9)	0.0586 (6)
H14	0.545321	0.134254	0.521051	0.070*
C15	0.59196 (14)	0.3697 (3)	0.51393 (9)	0.0611 (6)
H15	0.591165	0.373799	0.473205	0.073*
C16	0.62103 (12)	0.5076 (3)	0.54551 (9)	0.0537 (6)
C17	0.62057 (13)	0.5029 (3)	0.60578 (10)	0.0592 (6)
H17	0.639820	0.595723	0.627203	0.071*
C18	0.59139 (14)	0.3598 (3)	0.63427 (9)	0.0601 (6)
H18	0.589963	0.357611	0.675011	0.072*
C19	0.68915 (18)	0.7775 (3)	0.54377 (13)	0.0909 (9)
H19A	0.711215	0.857935	0.516175	0.136*
H19B	0.732795	0.733090	0.567635	0.136*
H19C	0.649438	0.833600	0.568244	0.136*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0844 (11)	0.0660 (11)	0.0644 (10)	−0.0169 (9)	0.0010 (8)	0.0117 (9)
N1	0.0580 (12)	0.0545 (11)	0.0542 (11)	−0.0044 (10)	0.0001 (9)	0.0066 (9)
C1	0.0562 (14)	0.0549 (14)	0.0536 (13)	−0.0036 (12)	0.0058 (11)	−0.0073 (11)
C2	0.0610 (15)	0.0695 (16)	0.0602 (14)	−0.0034 (13)	0.0033 (12)	−0.0064 (12)
C3	0.0639 (17)	0.093 (2)	0.0688 (16)	−0.0055 (15)	0.0041 (13)	−0.0164 (16)
C4	0.0749 (19)	0.096 (2)	0.0758 (18)	−0.0262 (16)	0.0184 (16)	−0.0219 (17)
C5	0.0855 (19)	0.0682 (16)	0.0678 (17)	−0.0190 (15)	0.0196 (15)	−0.0063 (14)
C6	0.0686 (16)	0.0521 (14)	0.0521 (13)	−0.0033 (12)	0.0149 (12)	−0.0058 (11)
C7	0.0701 (16)	0.0509 (13)	0.0500 (12)	0.0042 (12)	0.0148 (12)	0.0004 (11)
C8	0.0606 (14)	0.0560 (14)	0.0473 (12)	0.0053 (12)	0.0051 (11)	0.0015 (11)
C9	0.095 (2)	0.0605 (16)	0.0564 (15)	0.0038 (14)	0.0129 (14)	0.0084 (12)
C10	0.100 (2)	0.0733 (18)	0.0646 (16)	0.0181 (17)	−0.0011 (15)	0.0085 (14)
C11	0.0751 (17)	0.0827 (19)	0.0658 (16)	0.0164 (15)	−0.0052 (13)	−0.0009 (15)
C12	0.0655 (16)	0.0662 (15)	0.0596 (14)	0.0036 (13)	0.0039 (12)	0.0032 (13)
C13	0.0537 (13)	0.0495 (13)	0.0517 (13)	−0.0010 (10)	0.0008 (10)	0.0035 (11)
C14	0.0675 (15)	0.0564 (14)	0.0519 (13)	−0.0082 (12)	0.0000 (11)	−0.0044 (11)
C15	0.0713 (16)	0.0668 (16)	0.0452 (13)	−0.0062 (13)	0.0025 (11)	−0.0006 (12)
C16	0.0533 (13)	0.0542 (14)	0.0538 (14)	−0.0003 (11)	0.0036 (10)	0.0070 (12)
C17	0.0712 (15)	0.0509 (14)	0.0557 (14)	−0.0066 (12)	0.0018 (11)	−0.0055 (12)
C18	0.0753 (16)	0.0578 (14)	0.0471 (12)	−0.0026 (13)	0.0034 (11)	−0.0008 (12)
C19	0.113 (2)	0.0664 (18)	0.093 (2)	−0.0338 (16)	−0.0148 (17)	0.0135 (16)

Geometric parameters (Å, º) top

O1—C16	1.373 (2)	C9—H9	0.9300
O1—C19	1.414 (3)	C10—C11	1.390 (3)
N1—C8	1.395 (3)	C10—H10	0.9300
N1—C1	1.396 (3)	C11—C12	1.380 (3)
N1—C13	1.429 (3)	C11—H11	0.9300
C1—C2	1.388 (3)	C12—H12	0.9300
C1—C6	1.404 (3)	C13—C18	1.374 (3)
C2—C3	1.379 (3)	C13—C14	1.385 (3)
C2—H2	0.9300	C14—C15	1.369 (3)
C3—C4	1.387 (4)	C14—H14	0.9300
C3—H3	0.9300	C15—C16	1.381 (3)
C4—C5	1.372 (4)	C15—H15	0.9300
C4—H4	0.9300	C16—C17	1.376 (3)
C5—C6	1.395 (3)	C17—C18	1.380 (3)
C5—H5	0.9300	C17—H17	0.9300
C6—C7	1.439 (3)	C18—H18	0.9300
C7—C9	1.392 (3)	C19—H19A	0.9600
C7—C8	1.400 (3)	C19—H19B	0.9600
C8—C12	1.384 (3)	C19—H19C	0.9600
C9—C10	1.368 (3)

C16—O1—C19	117.80 (18)	C9—C10—H10	119.6
C8—N1—C1	108.32 (17)	C11—C10—H10	119.6
C8—N1—C13	125.53 (18)	C12—C11—C10	121.6 (2)
C1—N1—C13	126.13 (18)	C12—C11—H11	119.2
C2—C1—N1	129.2 (2)	C10—C11—H11	119.2
C2—C1—C6	122.1 (2)	C11—C12—C8	117.4 (2)
N1—C1—C6	108.73 (19)	C11—C12—H12	121.3
C3—C2—C1	117.3 (2)	C8—C12—H12	121.3
C3—C2—H2	121.3	C18—C13—C14	119.1 (2)
C1—C2—H2	121.3	C18—C13—N1	120.36 (18)
C2—C3—C4	121.3 (3)	C14—C13—N1	120.57 (19)
C2—C3—H3	119.4	C15—C14—C13	120.5 (2)
C4—C3—H3	119.4	C15—C14—H14	119.8
C5—C4—C3	121.5 (2)	C13—C14—H14	119.8
C5—C4—H4	119.2	C14—C15—C16	120.1 (2)
C3—C4—H4	119.2	C14—C15—H15	120.0
C4—C5—C6	118.7 (2)	C16—C15—H15	120.0
C4—C5—H5	120.7	O1—C16—C17	123.9 (2)
C6—C5—H5	120.7	O1—C16—C15	116.10 (19)
C5—C6—C1	119.1 (2)	C17—C16—C15	119.9 (2)
C5—C6—C7	133.9 (2)	C16—C17—C18	119.6 (2)
C1—C6—C7	106.99 (19)	C16—C17—H17	120.2
C9—C7—C8	119.4 (2)	C18—C17—H17	120.2
C9—C7—C6	133.5 (2)	C13—C18—C17	120.8 (2)
C8—C7—C6	107.15 (19)	C13—C18—H18	119.6
C12—C8—N1	129.4 (2)	C17—C18—H18	119.6
C12—C8—C7	121.8 (2)	O1—C19—H19A	109.5
N1—C8—C7	108.81 (19)	O1—C19—H19B	109.5
C10—C9—C7	119.1 (2)	H19A—C19—H19B	109.5
C10—C9—H9	120.4	O1—C19—H19C	109.5
C7—C9—H9	120.4	H19A—C19—H19C	109.5
C9—C10—C11	120.7 (2)	H19B—C19—H19C	109.5

C8—N1—C1—C2	178.5 (2)	C9—C7—C8—N1	−179.75 (18)
C13—N1—C1—C2	−0.1 (3)	C6—C7—C8—N1	0.4 (2)
C8—N1—C1—C6	−0.6 (2)	C8—C7—C9—C10	−1.4 (3)
C13—N1—C1—C6	−179.14 (18)	C6—C7—C9—C10	178.4 (2)
N1—C1—C2—C3	179.7 (2)	C7—C9—C10—C11	−0.4 (4)
C6—C1—C2—C3	−1.3 (3)	C9—C10—C11—C12	1.0 (4)
C1—C2—C3—C4	0.6 (3)	C10—C11—C12—C8	0.2 (3)
C2—C3—C4—C5	0.1 (4)	N1—C8—C12—C11	−179.1 (2)
C3—C4—C5—C6	0.0 (4)	C7—C8—C12—C11	−2.1 (3)
C4—C5—C6—C1	−0.7 (3)	C8—N1—C13—C18	−55.6 (3)
C4—C5—C6—C7	178.9 (2)	C1—N1—C13—C18	122.8 (2)
C2—C1—C6—C5	1.4 (3)	C8—N1—C13—C14	123.9 (2)
N1—C1—C6—C5	−179.44 (19)	C1—N1—C13—C14	−57.8 (3)
C2—C1—C6—C7	−178.32 (19)	C18—C13—C14—C15	1.1 (3)
N1—C1—C6—C7	0.8 (2)	N1—C13—C14—C15	−178.38 (19)
C5—C6—C7—C9	−0.3 (4)	C13—C14—C15—C16	0.7 (3)
C1—C6—C7—C9	179.5 (2)	C19—O1—C16—C17	5.2 (3)
C5—C6—C7—C8	179.6 (2)	C19—O1—C16—C15	−173.4 (2)
C1—C6—C7—C8	−0.7 (2)	C14—C15—C16—O1	177.25 (19)
C1—N1—C8—C12	177.4 (2)	C14—C15—C16—C17	−1.4 (3)
C13—N1—C8—C12	−4.1 (3)	O1—C16—C17—C18	−178.16 (19)
C1—N1—C8—C7	0.1 (2)	C15—C16—C17—C18	0.4 (3)
C13—N1—C8—C7	178.68 (18)	C14—C13—C18—C17	−2.1 (3)
C9—C7—C8—C12	2.7 (3)	N1—C13—C18—C17	177.35 (19)
C6—C7—C8—C12	−177.11 (19)	C16—C17—C18—C13	1.4 (3)

Acknowledgements

The authors thank DST–FIST for instrument facilities at the School of Chemistry, Bharathidasan University, Tiruchirappalli, Tamil Nadu, India. The authors also thank the SC-XRD Lab, SAS, VIT Vellore, Tamil Nadu, India.

Funding information

Funding for this research was provided by: UGC-BSR-RFSMS (scholarship to PG); UGC-EMERITUS (award to RR); UGC-DSK-PDF [award No. F.4-2/2006 (BSR)/CH/18-19/0165(80th List)/18th March 2019 to NJJ]; Bishop Heber College {grant No. [MRP/1911/2019 (BHC)] to RSD}.

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