3-Bromo-9-(4-chloro­benz­yl)-9H-carbazole

Xiao, Z.-D.; Pan, T.; Yang, D.-W.

doi:10.1107/S1600536809019448

organic compounds

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Volume 65| Part 7| July 2009| Page o1476

doi:10.1107/S1600536809019448

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3-Bromo-9-(4-chlorobenzyl)-9H-carbazole

Zi-Dan Xiao,^a Tong Pan ^a and Dao-Wu Yang ^a ^*

^aCollege of Chemistry and Bioengineering, Changsha University of Science and Technology, Changsha 410076, People's Republic of China
^*Correspondence e-mail: xiaozidan2009@126.com

(Received 13 May 2009; accepted 22 May 2009; online 6 June 2009)

The title compound, C₁₉H₁₃BrClN, was synthesized by N-alkylation of 4-chloro-1-(chloromethyl)benzene with 3-bromo-9H-carbazole. The carbazole ring system is essentially planar, with a mean deviation of 0.028 Å, and it makes a dihedral angle of 91.2 (3) Å with the plane of the benzene ring.

Related literature

For the pharmaceutical properties of the title compound, see: Buu-Hoï & Royer (1950 ); Caulfield et al. (2002 ); Harfenist & Joyner (1983 ); Harper et al. (2002 ). For bond-length data, see Allen et al. (1987 ). For synthetic procedures, see: Duan et al. (2005a ,b ).

Experimental

Crystal data

C₁₉H₁₃BrClN
M_r = 370.66
Orthorhombic, P n a 2₁
a = 17.272 (4) Å
b = 15.789 (3) Å
c = 5.5948 (11) Å
V = 1525.7 (5) Å³
Z = 4
Mo Kα radiation
μ = 2.86 mm⁻¹
T = 113 K
0.18 × 0.16 × 0.08 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.627, T_max = 0.803
10796 measured reflections
2664 independent reflections
2401 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.023
wR(F²) = 0.056
S = 1.04
2664 reflections
199 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.47 e Å⁻³
Absolute structure: Flack (1983 ), 1163 Friedel pairs
Flack parameter: 0.014 (9)

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809019448/dn2457sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809019448/dn2457Isup2.hkl

checkCIF report

Comment top

Carbazole derivatives substituted by N-alkylation possess valuable pharmaceutical properties (Buu-Hoï & Royer, 1950; Harfenist & Joyner, 1983; Caulfield et al., 2002; Harper et al., 2002). In this paper, the structure of 3-bromo-9-(4-chlorobenzyl)-9H-carbazole (I), synthesized by N-alkylation of 1-(chloromethyl)-4-chloroobenzene with 3-bromo-9H-carbazole, is reported

The carbazole ring is essentially planar, with mean deviations of 0.0275 Å. The dihedral angle between the carbazole ring and the benzyl ring is 91.2° A. The C—Br distance is 1.909 (3) Å, consistent with the literature (Allen et al., 1987).

Related literature top

For the pharmaceutical properties of the title compound, see: Buu-Hoï & Royer (1950); Caulfield et al. (2002); Harfenist & Joyner (1983); Harper et al. (2002). For related structures, see Allen et al. (1987). For related synthesis, see: Duan et al. (2005a,b).

Experimental top

The title compound was prepared according to the procedure of Duan et al. (2005a,b). A solution of potassium hydroxide (0.67 g) in dimethylformamide (8 ml) was stirred at room temperature for 20 min. 3-Bromo-9H-carbazole (1.0 g, 4 mmol) was added and the mixture stirred for a further 40 min. A solution of 1-(chloromethyl)-4-chlorobenzene (0.97 g, 6 mmol) in dimethylformamide (5 ml) was added dropwise with stirring. The resulting mixture was then stirred at room temperature for 12 h and poured into water (100 ml), yielding a white precipitate. The solid product was filtered off, washed with cold water and recrystallized from EtOH, giving crystals of (I). Yield: 1.26 g (85.2%); m.p. 431 - 433 K. Compound (I) (40 mg) was dissolved in mixture of chloroform (5 ml) and ethanol (5 ml) and the solution was kept at room temperature for 14 d. Natural evaporation of the solution gave colourless crystals suitable for X-Ray analysis.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. A view of the molecular structure of (I). Displacement ellipsoids are drawn at the 30% probability level (arbitrary spheres for H atoms).

3-Bromo-9-(4-chlorobenzyl)-9H-carbazole top

Crystal data top

C₁₉H₁₃BrClN	D_x = 1.614 Mg m⁻³
M_r = 370.66	Melting point: 432 K
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 5012 reflections
a = 17.272 (4) Å	θ = 1.8–27.9°
b = 15.789 (3) Å	µ = 2.86 mm⁻¹
c = 5.5948 (11) Å	T = 113 K
V = 1525.7 (5) Å³	Block, colorless
Z = 4	0.18 × 0.16 × 0.08 mm
F(000) = 744

Data collection top

Rigaku Saturn CCD area-detector diffractometer	2664 independent reflections
Radiation source: rotating anode	2401 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.031
Detector resolution: 7.31 pixels mm^-1	θ_max = 25.0°, θ_min = 1.8°
ω and ϕ scans	h = −20→19
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −18→18
T_min = 0.627, T_max = 0.803	l = −6→6
10796 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.023	H-atom parameters constrained
wR(F²) = 0.056	w = 1/[σ²(F_o²) + (0.0295P)²] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
2664 reflections	Δρ_max = 0.38 e Å⁻³
199 parameters	Δρ_min = −0.47 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1163 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.014 (9)

Crystal data top

C₁₉H₁₃BrClN	V = 1525.7 (5) Å³
M_r = 370.66	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 17.272 (4) Å	µ = 2.86 mm⁻¹
b = 15.789 (3) Å	T = 113 K
c = 5.5948 (11) Å	0.18 × 0.16 × 0.08 mm

Data collection top

Rigaku Saturn CCD area-detector diffractometer	2664 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	2401 reflections with I > 2σ(I)
T_min = 0.627, T_max = 0.803	R_int = 0.031
10796 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.023	H-atom parameters constrained
wR(F²) = 0.056	Δρ_max = 0.38 e Å⁻³
S = 1.04	Δρ_min = −0.47 e Å⁻³
2664 reflections	Absolute structure: Flack (1983), 1163 Friedel pairs
199 parameters	Absolute structure parameter: 0.014 (9)
1 restraint

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) 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
Br1	0.258680 (12)	0.185476 (15)	1.32912 (10)	0.02288 (9)
Cl1	0.65120 (4)	0.59416 (4)	0.8259 (2)	0.02847 (16)
N1	0.53701 (13)	0.18736 (14)	0.6844 (4)	0.0167 (5)
C1	0.58534 (13)	0.13162 (15)	0.8041 (6)	0.0152 (6)
C2	0.66094 (15)	0.10636 (17)	0.7491 (5)	0.0209 (7)
H2	0.6862	0.1270	0.6143	0.025*
C3	0.69681 (15)	0.04979 (18)	0.9013 (5)	0.0224 (7)
H3	0.7471	0.0322	0.8682	0.027*
C4	0.65932 (16)	0.01831 (19)	1.1042 (6)	0.0233 (7)
H4	0.6848	−0.0198	1.2038	0.028*
C5	0.58446 (15)	0.04349 (18)	1.1579 (5)	0.0186 (7)
H5	0.5597	0.0227	1.2934	0.022*
C6	0.54667 (15)	0.10001 (16)	1.0080 (5)	0.0167 (6)
C7	0.47140 (14)	0.13996 (16)	1.0130 (5)	0.0135 (6)
C8	0.40812 (14)	0.13595 (18)	1.1675 (5)	0.0160 (6)
H8	0.4082	0.1001	1.2993	0.019*
C9	0.34553 (15)	0.18694 (17)	1.1181 (5)	0.0174 (6)
C10	0.34293 (15)	0.24129 (18)	0.9223 (5)	0.0210 (7)
H10	0.2993	0.2746	0.8960	0.025*
C11	0.40475 (15)	0.24581 (18)	0.7676 (5)	0.0202 (7)
H11	0.4040	0.2824	0.6373	0.024*
C12	0.46844 (13)	0.19405 (14)	0.8117 (6)	0.0147 (5)
C13	0.55872 (15)	0.24502 (16)	0.4941 (5)	0.0193 (7)
H13A	0.5160	0.2495	0.3822	0.023*
H13B	0.6026	0.2214	0.4087	0.023*
C14	0.57980 (15)	0.33317 (17)	0.5812 (5)	0.0151 (6)
C15	0.62228 (15)	0.34401 (18)	0.7921 (6)	0.0227 (7)
H15	0.6358	0.2971	0.8835	0.027*
C16	0.64432 (14)	0.42472 (17)	0.8658 (6)	0.0215 (7)
H16	0.6729	0.4319	1.0052	0.026*
C17	0.62343 (16)	0.49356 (17)	0.7311 (5)	0.0187 (6)
C18	0.58085 (15)	0.48457 (18)	0.5212 (6)	0.0223 (7)
H18	0.5671	0.5318	0.4313	0.027*
C19	0.55924 (15)	0.40353 (17)	0.4486 (5)	0.0192 (7)
H19	0.5306	0.3967	0.3091	0.023*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.01586 (13)	0.02907 (15)	0.02370 (15)	0.00028 (9)	0.0041 (2)	−0.0042 (2)
Cl1	0.0313 (3)	0.0172 (3)	0.0370 (4)	−0.0025 (2)	0.0062 (6)	−0.0066 (5)
N1	0.0162 (12)	0.0175 (14)	0.0164 (13)	−0.0024 (9)	0.0028 (10)	0.0012 (10)
C1	0.0157 (11)	0.0141 (13)	0.0159 (16)	−0.0043 (9)	−0.0006 (15)	−0.0046 (15)
C2	0.0167 (14)	0.0249 (17)	0.0210 (17)	−0.0076 (12)	0.0033 (11)	−0.0064 (12)
C3	0.0131 (14)	0.0229 (17)	0.031 (2)	0.0027 (11)	−0.0004 (12)	−0.0099 (13)
C4	0.0196 (16)	0.0219 (17)	0.0283 (18)	0.0007 (13)	−0.0074 (13)	−0.0015 (14)
C5	0.0187 (16)	0.0179 (16)	0.0193 (16)	−0.0019 (12)	−0.0037 (13)	−0.0021 (12)
C6	0.0161 (14)	0.0147 (16)	0.0192 (16)	−0.0050 (11)	−0.0006 (12)	−0.0059 (13)
C7	0.0121 (13)	0.0118 (15)	0.0166 (15)	−0.0036 (10)	−0.0011 (12)	−0.0024 (12)
C8	0.0184 (15)	0.0137 (16)	0.0159 (16)	−0.0045 (11)	−0.0051 (12)	−0.0018 (12)
C9	0.0128 (13)	0.0187 (16)	0.0208 (17)	−0.0032 (12)	0.0023 (12)	−0.0078 (13)
C10	0.0161 (15)	0.0222 (17)	0.0248 (17)	0.0011 (11)	−0.0055 (12)	−0.0029 (13)
C11	0.0232 (14)	0.0199 (15)	0.017 (2)	−0.0010 (11)	−0.0014 (12)	0.0006 (12)
C12	0.0155 (11)	0.0150 (13)	0.0137 (14)	−0.0051 (9)	0.0017 (18)	−0.0022 (16)
C13	0.0193 (15)	0.0235 (17)	0.0151 (15)	−0.0050 (12)	0.0030 (13)	−0.0026 (14)
C14	0.0138 (14)	0.0174 (15)	0.0142 (15)	−0.0024 (11)	0.0050 (12)	0.0002 (12)
C15	0.0235 (13)	0.0193 (14)	0.025 (2)	−0.0009 (10)	−0.0009 (16)	0.0049 (15)
C16	0.0220 (13)	0.0251 (16)	0.017 (2)	−0.0035 (10)	0.0012 (14)	−0.0007 (14)
C17	0.0181 (14)	0.0149 (16)	0.0229 (16)	−0.0008 (11)	0.0056 (12)	−0.0012 (12)
C18	0.0201 (15)	0.0194 (17)	0.0273 (18)	0.0039 (12)	0.0024 (14)	0.0017 (14)
C19	0.0145 (14)	0.0261 (18)	0.0172 (16)	0.0001 (11)	0.0007 (12)	0.0013 (13)

Geometric parameters (Å, º) top

Br1—C9	1.909 (3)	C8—H8	0.9300
Cl1—C17	1.742 (3)	C9—C10	1.392 (4)
N1—C1	1.385 (3)	C10—C11	1.376 (4)
N1—C12	1.386 (3)	C10—H10	0.9300
N1—C13	1.450 (3)	C11—C12	1.393 (4)
C1—C2	1.399 (3)	C11—H11	0.9300
C1—C6	1.413 (4)	C13—C14	1.519 (4)
C2—C3	1.381 (4)	C13—H13A	0.9700
C2—H2	0.9300	C13—H13B	0.9700
C3—C4	1.398 (4)	C14—C19	1.382 (4)
C3—H3	0.9300	C14—C15	1.400 (4)
C4—C5	1.386 (4)	C15—C16	1.392 (4)
C4—H4	0.9300	C15—H15	0.9300
C5—C6	1.388 (4)	C16—C17	1.371 (4)
C5—H5	0.9300	C16—H16	0.9300
C6—C7	1.445 (3)	C17—C18	1.393 (4)
C7—C8	1.395 (4)	C18—C19	1.393 (4)
C7—C12	1.415 (4)	C18—H18	0.9300
C8—C9	1.376 (4)	C19—H19	0.9300

C1—N1—C12	108.4 (2)	C9—C10—H10	119.9
C1—N1—C13	126.7 (2)	C10—C11—C12	118.1 (3)
C12—N1—C13	123.4 (2)	C10—C11—H11	121.0
N1—C1—C2	129.6 (3)	C12—C11—H11	121.0
N1—C1—C6	109.2 (2)	N1—C12—C11	129.0 (3)
C2—C1—C6	121.2 (3)	N1—C12—C7	109.4 (2)
C3—C2—C1	117.9 (3)	C11—C12—C7	121.6 (3)
C3—C2—H2	121.1	N1—C13—C14	113.7 (2)
C1—C2—H2	121.1	N1—C13—H13A	108.8
C2—C3—C4	121.5 (3)	C14—C13—H13A	108.8
C2—C3—H3	119.2	N1—C13—H13B	108.8
C4—C3—H3	119.2	C14—C13—H13B	108.8
C5—C4—C3	120.4 (3)	H13A—C13—H13B	107.7
C5—C4—H4	119.8	C19—C14—C15	119.3 (3)
C3—C4—H4	119.8	C19—C14—C13	120.2 (3)
C4—C5—C6	119.5 (3)	C15—C14—C13	120.5 (3)
C4—C5—H5	120.3	C16—C15—C14	120.3 (3)
C6—C5—H5	120.3	C16—C15—H15	119.8
C5—C6—C1	119.5 (2)	C14—C15—H15	119.8
C5—C6—C7	133.8 (3)	C17—C16—C15	119.4 (3)
C1—C6—C7	106.7 (2)	C17—C16—H16	120.3
C8—C7—C12	119.5 (2)	C15—C16—H16	120.3
C8—C7—C6	134.2 (3)	C16—C17—C18	121.4 (3)
C12—C7—C6	106.3 (2)	C16—C17—Cl1	118.9 (2)
C9—C8—C7	117.7 (3)	C18—C17—Cl1	119.7 (2)
C9—C8—H8	121.2	C17—C18—C19	118.8 (3)
C7—C8—H8	121.2	C17—C18—H18	120.6
C8—C9—C10	123.0 (3)	C19—C18—H18	120.6
C8—C9—Br1	119.1 (2)	C14—C19—C18	120.8 (3)
C10—C9—Br1	117.9 (2)	C14—C19—H19	119.6
C11—C10—C9	120.1 (3)	C18—C19—H19	119.6
C11—C10—H10	119.9

C12—N1—C1—C2	−178.2 (3)	C9—C10—C11—C12	0.8 (4)
C13—N1—C1—C2	−12.0 (4)	C1—N1—C12—C11	176.2 (3)
C12—N1—C1—C6	1.6 (3)	C13—N1—C12—C11	9.5 (4)
C13—N1—C1—C6	167.8 (2)	C1—N1—C12—C7	−1.7 (3)
N1—C1—C2—C3	179.4 (3)	C13—N1—C12—C7	−168.4 (2)
C6—C1—C2—C3	−0.4 (4)	C10—C11—C12—N1	−179.6 (3)
C1—C2—C3—C4	0.1 (4)	C10—C11—C12—C7	−1.9 (4)
C2—C3—C4—C5	−0.1 (4)	C8—C7—C12—N1	−179.7 (2)
C3—C4—C5—C6	0.3 (4)	C6—C7—C12—N1	1.2 (3)
C4—C5—C6—C1	−0.6 (4)	C8—C7—C12—C11	2.2 (4)
C4—C5—C6—C7	−178.3 (3)	C6—C7—C12—C11	−177.0 (2)
N1—C1—C6—C5	−179.2 (2)	C1—N1—C13—C14	−93.3 (3)
C2—C1—C6—C5	0.6 (4)	C12—N1—C13—C14	70.8 (3)
N1—C1—C6—C7	−0.9 (3)	N1—C13—C14—C19	−142.8 (3)
C2—C1—C6—C7	178.9 (2)	N1—C13—C14—C15	39.3 (4)
C5—C6—C7—C8	−1.2 (5)	C19—C14—C15—C16	−0.7 (4)
C1—C6—C7—C8	−179.1 (3)	C13—C14—C15—C16	177.2 (2)
C5—C6—C7—C12	177.8 (3)	C14—C15—C16—C17	0.6 (4)
C1—C6—C7—C12	−0.1 (3)	C15—C16—C17—C18	−0.3 (4)
C12—C7—C8—C9	−1.3 (4)	C15—C16—C17—Cl1	179.8 (2)
C6—C7—C8—C9	177.6 (3)	C16—C17—C18—C19	0.1 (4)
C7—C8—C9—C10	0.2 (4)	Cl1—C17—C18—C19	180.0 (2)
C7—C8—C9—Br1	−178.51 (19)	C15—C14—C19—C18	0.6 (4)
C8—C9—C10—C11	0.0 (4)	C13—C14—C19—C18	−177.4 (2)
Br1—C9—C10—C11	178.8 (2)	C17—C18—C19—C14	−0.2 (4)

Experimental details

Crystal data
Chemical formula	C₁₉H₁₃BrClN
M_r	370.66
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	113
a, b, c (Å)	17.272 (4), 15.789 (3), 5.5948 (11)
V (Å³)	1525.7 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.86
Crystal size (mm)	0.18 × 0.16 × 0.08

Data collection
Diffractometer	Rigaku Saturn CCD area-detector diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.627, 0.803
No. of measured, independent and observed [I > 2σ(I)] reflections	10796, 2664, 2401
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.023, 0.056, 1.04
No. of reflections	2664
No. of parameters	199
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.47
Absolute structure	Flack (1983), 1163 Friedel pairs
Absolute structure parameter	0.014 (9)

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

This work was supported by the Hunan Natural Science Foundation (05 J J30198) and the Scientific Research Foundation of Hunan Province (2008 GK-037).

References

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