3,6-Di­chloro-9-(prop-2-yn-1-yl)-9H-carbazole

Mague, J.T.; Akkurt, M.; Mohamed, S.K.; Mohamed, A.H.; Albayati, M.R.

doi:10.1107/S1600536813032777

organic compounds

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ISSN: 2056-9890

Volume 70| Part 1| January 2014| Page o27

https://doi.org/10.1107/S1600536813032777

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3,6-Dichloro-9-(prop-2-yn-1-yl)-9H-carbazole

Joel T. Mague,^a Mehmet Akkurt,^b Shaaban K. Mohamed,^c,^d Asmaa H. Mohamed ^d and Mustafa R. Albayati ^e ^*

^aDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, ^bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^cChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, ^dChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, and ^eKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
^*Correspondence e-mail: shaabankamel@yahoo.com

(Received 22 November 2013; accepted 3 December 2013; online 7 December 2013)

The tricyclic aromatic ring system of the title compound, C₁₅H₉Cl₂N, is essentially planar (r.m.s. deviation = 0.002 Å). The two Cl atoms lie slightly out of the plane of the carbazole ring system, with the C—Cl bonds forming angles of 1.23 (8) and 1.14 (8)° with the plane. The acetylene group has a syn orientation with respect to the ring system. In the crystal, no weak hydrogen bonds nor any π–π stacking interactions are observed.

CCDC reference: 974842

Related literature

For industrial applications of carbazole-containing compounds, see: Zhang et al. (1998 ). For pharmaceutical properties of carbazoles, see: Liu & Larock (2007 ); Hussain et al. (2011 ); Zhang et al. (2010 ); Conchon et al. (2006 ). For a related structure, see: Xie et al. (2012 ).

Experimental

Crystal data

C₁₅H₉Cl₂N
M_r = 274.13
Orthorhombic, P 2₁ 2₁ 2₁
a = 3.9825 (1) Å
b = 11.1705 (4) Å
c = 27.4417 (9) Å
V = 1220.79 (7) Å³
Z = 4
Cu Kα radiation
μ = 4.59 mm⁻¹
T = 100 K
0.18 × 0.05 × 0.02 mm

Data collection

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2013 ) T_min = 0.74, T_max = 0.91
10712 measured reflections
2224 independent reflections
2160 reflections with I > 2σ(I)
R_int = 0.088

Refinement

R[F² > 2σ(F²)] = 0.026
wR(F²) = 0.068
S = 1.05
2224 reflections
163 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.18 e Å⁻³
Absolute structure: Flack parameter determined using 817 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013 )
Absolute structure parameter: −0.002 (12)

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT; program(s) used to solve structure: SHELXT (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 974842

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536813032777/lh5674sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813032777/lh5674Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536813032777/lh5674Isup3.cml

checkCIF report

Comment top

In recent years, carbazoles have been used as photoconductors, semiconductors and for their light-emitting properties, making them interesting organic tools for physics experiments (Zhang et al., 1998). Moreover, several alkaloids based on a carbazole structure are known to possess interesting biological activities such as antitumor, antibacterial, anti-inflammatory, psychotropic and anti-histamine properties (Liu & Larock, 2007). Many synthetic carbazole derivatives are of significant pharmacological relevance because of their antifungal, antibiotic, and antitumor activities (Hussain et al., 2011; Zhang et al., 2010; Conchon et al., 2006). The introduction of functional groups onto the carbazole scaffold is essential to generate compounds suitable for biological and physical investigations. Based on such facts we herein report the crystal structure of the title compound.

In the title compound (Fig. 1), the carbazole ring system is essentially planar (r.m.s. deviation = 0.002 Å). The Cl1 and Cl2 atoms lie slightly out of the plane of the carbazole ring system which makes angles of 1.23 (8) and 1.14 (8)° with the Cl1—C4 and Cl2—C9 bonds, respectively. The values of the geometric parameters of the title compound are within normal ranges (Xie et al., 2012).

In the crystal, no classical hydrogen bonds are observed. The crystal packing is stabilized by weak van der Waals interactions. The packing of the title compound viewed along the a axis are shown in Fig. 2.

Related literature top

For industrial applications of carbazole-containing compounds, see: Zhang et al. (1998). For pharmaceutical properties of carbazoles, see: Liu & Larock (2007); Hussain et al. (2011); Zhang et al. (2010); Conchon et al. (2006). For a related structure, see: Xie et al. (2012).

Experimental top

Propargyl bromide (1.1 g, 9 mmol) was added to a suspension solution of 3,6-dichloro-9H-carbazole (0.7 g, 3 mmol) and K₂CO₃ (0.82 g, 6 mmol) in DMF (15 ml) and stirred at room temperature for 6 h. The excess solvent was evaporated to dryness in vacuo. The residue was diluted with water and then extracted with CH₂Cl₂ (3 x 30 ml). The combined organic extracts were dried over anhydrous Na₂SO₄, filtered and evaporated under reduced pressure to give the corresponding product as colourless crystals (0.61 g, 75%) yield, mp 469–471 K.

Structure description top

For industrial applications of carbazole-containing compounds, see: Zhang et al. (1998). For pharmaceutical properties of carbazoles, see: Liu & Larock (2007); Hussain et al. (2011); Zhang et al. (2010); Conchon et al. (2006). For a related structure, see: Xie et al. (2012).

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXT (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Figures top

	Fig. 1. Perspective view of the title compound with 50% probability ellipsoids.
	Fig. 2. Packing of the title compound viewed along the a axis.

3,6-Dichloro-9-(prop-2-yn-1-yl)-9H-carbazole top

Crystal data top

C₁₅H₉Cl₂N	F(000) = 560
M_r = 274.13	D_x = 1.492 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2ac 2ab	Cell parameters from 9151 reflections
a = 3.9825 (1) Å	θ = 4.3–68.0°
b = 11.1705 (4) Å	µ = 4.59 mm⁻¹
c = 27.4417 (9) Å	T = 100 K
V = 1220.79 (7) Å³	Column, colourless
Z = 4	0.18 × 0.05 × 0.02 mm

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	2224 independent reflections
Radiation source: INCOATEC IµS micro–focus source	2160 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.088
Detector resolution: 10.4167 pixels mm^-1	θ_max = 68.1°, θ_min = 3.2°
ω scans	h = −4→4
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −13→13
T_min = 0.74, T_max = 0.91	l = −32→33
10712 measured 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)] = 0.026	W = 1/[Σ²(FO²) + (0.0351P)² + 0.195P] where P = (FO² + 2FC²)/3
wR(F²) = 0.068	(Δ/σ)_max < 0.001
S = 1.05	Δρ_max = 0.22 e Å⁻³
2224 reflections	Δρ_min = −0.18 e Å⁻³
163 parameters	Absolute structure: Flack parameter determined using 817 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
0 restraints	Absolute structure parameter: −0.002 (12)

Crystal data top

C₁₅H₉Cl₂N	V = 1220.79 (7) Å³
M_r = 274.13	Z = 4
Orthorhombic, P2₁2₁2₁	Cu Kα radiation
a = 3.9825 (1) Å	µ = 4.59 mm⁻¹
b = 11.1705 (4) Å	T = 100 K
c = 27.4417 (9) Å	0.18 × 0.05 × 0.02 mm

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	2224 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2013)	2160 reflections with I > 2σ(I)
T_min = 0.74, T_max = 0.91	R_int = 0.088
10712 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.026	H-atom parameters constrained
wR(F²) = 0.068	Δρ_max = 0.22 e Å⁻³
S = 1.05	Δρ_min = −0.18 e Å⁻³
2224 reflections	Absolute structure: Flack parameter determined using 817 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
163 parameters	Absolute structure parameter: −0.002 (12)
0 restraints

Special details top

Experimental. ¹H-NMR (300 MHz, CDCl₃): d 3.31 (s, 1H, C—CH), 5.34 (d, 2H, J=2.4 Hz, CH₂—C), 7.54 (m, 2H, Ar—H), 7.74 (m, 2H, Ar—H), 8.34 (s, 2H, Ar—H). 13 C-NMR (75 MHz, CDCl₃): d 32.2 (CH₂), 74.8 (C—CH), 78.5 (C—CH), 111.4, 120.5, (4CH-Ar), 122.9, 124.2 (4 C-Ar), 126.4 (2CH-Ar), 138.6 (2 C-Ar). MS: (EI) m/z (%): 275 (M+2, 70), 274 (M+1, 74), 273 (M+, 100), 247 (10), 233 (44), 201 (4), 174 (2), 164 (14), 150 (2), 122 (2), 98 (2), 75 (4). Anal. for C₁₅H₉Cl₂N: calcd. C, 65.72; H, 3.31; Cl, 25.86; N, 5.11. Found: C, 65.38; H, 3.11; N, 4.95%.

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.52328 (16)	0.39290 (5)	−0.06840 (2)	0.0240 (2)
Cl2	0.52780 (15)	0.15240 (5)	0.22392 (2)	0.0252 (2)
N1	0.0291 (5)	0.57255 (17)	0.11884 (6)	0.0190 (5)
C1	0.1356 (6)	0.5462 (2)	0.07181 (8)	0.0180 (6)
C2	0.0865 (6)	0.6107 (2)	0.02874 (8)	0.0218 (7)
C3	0.2076 (6)	0.5615 (2)	−0.01405 (8)	0.0214 (7)
C4	0.3762 (6)	0.4513 (2)	−0.01335 (8)	0.0197 (6)
C5	0.4309 (6)	0.3879 (2)	0.02890 (8)	0.0190 (6)
C6	0.3072 (6)	0.4360 (2)	0.07226 (8)	0.0175 (6)
C7	0.3067 (6)	0.3947 (2)	0.12215 (8)	0.0177 (6)
C8	0.4327 (6)	0.2920 (2)	0.14472 (8)	0.0188 (6)
C9	0.3751 (6)	0.2800 (2)	0.19418 (8)	0.0208 (7)
C10	0.2040 (6)	0.3660 (2)	0.22166 (8)	0.0217 (7)
C11	0.0803 (6)	0.4677 (2)	0.19960 (8)	0.0213 (7)
C12	0.1317 (6)	0.4812 (2)	0.14950 (8)	0.0183 (6)
C13	−0.1714 (6)	0.6755 (2)	0.13263 (9)	0.0219 (7)
C14	0.0264 (6)	0.7838 (2)	0.14305 (8)	0.0216 (6)
C15	0.1835 (7)	0.8710 (2)	0.15139 (10)	0.0284 (7)
H2	−0.02610	0.68560	0.02880	0.0260*
H3	0.17640	0.60250	−0.04400	0.0260*
H5	0.54890	0.31400	0.02860	0.0230*
H8	0.55280	0.23300	0.12690	0.0230*
H10	0.17270	0.35420	0.25560	0.0260*
H11	−0.03610	0.52690	0.21790	0.0260*
H13A	−0.30450	0.65470	0.16190	0.0260*
H13B	−0.33110	0.69340	0.10600	0.0260*
H15	0.31000	0.94120	0.15810	0.0340*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0287 (3)	0.0266 (3)	0.0167 (2)	−0.0027 (3)	0.0020 (2)	−0.0015 (2)
Cl2	0.0256 (3)	0.0274 (3)	0.0226 (3)	−0.0015 (3)	−0.0015 (2)	0.0073 (2)
N1	0.0184 (9)	0.0176 (9)	0.0209 (9)	−0.0002 (9)	0.0008 (8)	−0.0031 (7)
C1	0.0165 (11)	0.0170 (11)	0.0206 (11)	−0.0036 (9)	−0.0012 (9)	−0.0023 (9)
C2	0.0201 (11)	0.0185 (11)	0.0269 (12)	−0.0009 (10)	−0.0024 (9)	0.0002 (9)
C3	0.0221 (11)	0.0228 (12)	0.0192 (11)	−0.0057 (10)	−0.0024 (9)	0.0016 (10)
C4	0.0191 (11)	0.0212 (11)	0.0189 (11)	−0.0052 (9)	0.0009 (9)	−0.0023 (9)
C5	0.0186 (11)	0.0180 (11)	0.0204 (10)	−0.0036 (10)	0.0004 (9)	−0.0017 (9)
C6	0.0157 (10)	0.0174 (11)	0.0195 (11)	−0.0028 (9)	−0.0017 (9)	−0.0014 (9)
C7	0.0155 (10)	0.0188 (11)	0.0188 (11)	−0.0045 (9)	0.0006 (8)	−0.0018 (9)
C8	0.0168 (11)	0.0201 (10)	0.0194 (10)	−0.0028 (9)	−0.0008 (9)	−0.0028 (9)
C9	0.0178 (12)	0.0235 (12)	0.0211 (11)	−0.0056 (10)	−0.0038 (9)	0.0031 (10)
C10	0.0194 (11)	0.0291 (13)	0.0167 (10)	−0.0066 (10)	0.0015 (9)	−0.0024 (10)
C11	0.0193 (12)	0.0238 (12)	0.0207 (11)	−0.0041 (10)	0.0017 (9)	−0.0064 (9)
C12	0.0143 (11)	0.0188 (11)	0.0219 (11)	−0.0034 (9)	−0.0008 (9)	−0.0031 (9)
C13	0.0173 (11)	0.0208 (12)	0.0276 (12)	0.0012 (10)	0.0005 (9)	−0.0043 (10)
C14	0.0212 (12)	0.0219 (11)	0.0217 (10)	0.0062 (11)	0.0028 (10)	−0.0018 (9)
C15	0.0276 (12)	0.0206 (12)	0.0369 (14)	0.0005 (11)	0.0004 (11)	−0.0031 (11)

Geometric parameters (Å, º) top

Cl1—C4	1.747 (2)	C9—C10	1.399 (3)
Cl2—C9	1.751 (2)	C10—C11	1.378 (3)
N1—C1	1.390 (3)	C11—C12	1.398 (3)
N1—C12	1.384 (3)	C13—C14	1.472 (3)
N1—C13	1.450 (3)	C14—C15	1.180 (3)
C1—C2	1.398 (3)	C2—H2	0.9500
C1—C6	1.408 (3)	C3—H3	0.9500
C2—C3	1.383 (3)	C5—H5	0.9500
C3—C4	1.402 (3)	C8—H8	0.9500
C4—C5	1.376 (3)	C10—H10	0.9500
C5—C6	1.395 (3)	C11—H11	0.9500
C6—C7	1.445 (3)	C13—H13A	0.9900
C7—C8	1.397 (3)	C13—H13B	0.9900
C7—C12	1.408 (3)	C15—H15	0.9500
C8—C9	1.383 (3)

C1—N1—C12	108.55 (18)	N1—C12—C7	109.15 (19)
C1—N1—C13	125.32 (19)	N1—C12—C11	129.3 (2)
C12—N1—C13	126.05 (18)	C7—C12—C11	121.5 (2)
N1—C1—C2	129.3 (2)	N1—C13—C14	114.1 (2)
N1—C1—C6	108.97 (19)	C13—C14—C15	179.7 (3)
C2—C1—C6	121.7 (2)	C1—C2—H2	121.00
C1—C2—C3	117.7 (2)	C3—C2—H2	121.00
C2—C3—C4	120.3 (2)	C2—C3—H3	120.00
Cl1—C4—C3	118.46 (17)	C4—C3—H3	120.00
Cl1—C4—C5	118.91 (17)	C4—C5—H5	121.00
C3—C4—C5	122.6 (2)	C6—C5—H5	121.00
C4—C5—C6	117.7 (2)	C7—C8—H8	121.00
C1—C6—C5	120.0 (2)	C9—C8—H8	121.00
C1—C6—C7	106.67 (19)	C9—C10—H10	120.00
C5—C6—C7	133.3 (2)	C11—C10—H10	120.00
C6—C7—C8	133.0 (2)	C10—C11—H11	121.00
C6—C7—C12	106.66 (19)	C12—C11—H11	121.00
C8—C7—C12	120.3 (2)	N1—C13—H13A	109.00
C7—C8—C9	117.1 (2)	N1—C13—H13B	109.00
Cl2—C9—C8	118.59 (17)	C14—C13—H13A	109.00
Cl2—C9—C10	118.49 (17)	C14—C13—H13B	109.00
C8—C9—C10	122.9 (2)	H13A—C13—H13B	108.00
C9—C10—C11	120.2 (2)	C14—C15—H15	180.00
C10—C11—C12	117.9 (2)

C12—N1—C1—C2	178.9 (2)	C3—C4—C5—C6	1.0 (4)
C12—N1—C1—C6	0.4 (3)	C4—C5—C6—C1	−0.5 (3)
C13—N1—C1—C2	1.9 (4)	C4—C5—C6—C7	177.8 (2)
C13—N1—C1—C6	−176.6 (2)	C1—C6—C7—C8	179.0 (3)
C1—N1—C12—C7	0.0 (3)	C1—C6—C7—C12	0.6 (3)
C1—N1—C12—C11	−179.3 (2)	C5—C6—C7—C8	0.6 (5)
C13—N1—C12—C7	177.0 (2)	C5—C6—C7—C12	−177.8 (3)
C13—N1—C12—C11	−2.4 (4)	C6—C7—C8—C9	−177.8 (2)
C1—N1—C13—C14	−86.6 (3)	C12—C7—C8—C9	0.4 (3)
C12—N1—C13—C14	97.0 (3)	C6—C7—C12—N1	−0.4 (3)
N1—C1—C2—C3	−177.2 (2)	C6—C7—C12—C11	179.0 (2)
C6—C1—C2—C3	1.1 (4)	C8—C7—C12—N1	−179.1 (2)
N1—C1—C6—C5	178.1 (2)	C8—C7—C12—C11	0.3 (4)
N1—C1—C6—C7	−0.6 (3)	C7—C8—C9—Cl2	179.84 (17)
C2—C1—C6—C5	−0.6 (4)	C7—C8—C9—C10	−1.0 (4)
C2—C1—C6—C7	−179.3 (2)	Cl2—C9—C10—C11	179.94 (18)
C1—C2—C3—C4	−0.7 (3)	C8—C9—C10—C11	0.8 (4)
C2—C3—C4—Cl1	179.85 (18)	C9—C10—C11—C12	0.0 (3)
C2—C3—C4—C5	−0.4 (4)	C10—C11—C12—N1	178.7 (2)
Cl1—C4—C5—C6	−179.26 (18)	C10—C11—C12—C7	−0.6 (4)

Experimental details

Crystal data
Chemical formula	C₁₅H₉Cl₂N
M_r	274.13
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	100
a, b, c (Å)	3.9825 (1), 11.1705 (4), 27.4417 (9)
V (Å³)	1220.79 (7)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	4.59
Crystal size (mm)	0.18 × 0.05 × 0.02

Data collection
Diffractometer	Bruker D8 VENTURE PHOTON 100 CMOS
Absorption correction	Multi-scan (SADABS; Bruker, 2013)
T_min, T_max	0.74, 0.91
No. of measured, independent and observed [I > 2σ(I)] reflections	10712, 2224, 2160
R_int	0.088
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.026, 0.068, 1.05
No. of reflections	2224
No. of parameters	163
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.18
Absolute structure	Flack parameter determined using 817 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
Absolute structure parameter	−0.002 (12)

Computer programs: APEX2 (Bruker, 2013), SAINT (Bruker, 2013), SHELXT (Sheldrick, 2008), SHELXL2013 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Acknowledgements

The authors thank Minia University, Erciyes University, Tulane University and Manchester Metropolitan University for supporting the study.

References

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