9-(4-Methyl­benz­yl)-9H-carbazole

The title compound, C₂₀H₁₇N, was synthesized by N-alkyl­ation of 1-chloro­methyl-4-methyl­benzene with carbazole. The carbazole ring system is essentially planar, with a mean deviation of 0.029 Å, and makes a dihedral angle of 109 (5)° with the plane of the benzene ring.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.037
• wR factor = 0.091
• Data-to-parameter ratio = 9.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C17

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           26.45
           From the CIF: _reflns_number_total               1783
           Count of symmetry unique reflns         1785
           Completeness (_total/calc)             99.89%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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S1. Comment

Carbazole derivatives substituted by N-alkylation show useful pharmaceutical properties (Buu-Hoï & Royer, 1950; Harfenist & Joyner, 1983; Caulfield et al., 2002; Harper et al., 2002). In this paper, the structure of 9-(4-methyl-benzyl)-9H-carbazole (I) is reported, which was synthesized by N-alkylation of 1-chloromethyl-4-methyl-benzene with carbazole.

The carbazole ring is essentially planar, with mean deviations of 0.029 Å. The dihedral angle formed between the carbazole ring and methyl benzyl ring is 109 (su?)°.

S2. Experimental

The title compound was prepared according to the procedure of Duan et al. (2005). A solution of potassium hydroxide (7.0 g) in dimethylformamide (50 ml) was stirred at room temperature for 20 min. Carbazole (3.34 g, 20 mmol) was added and the mixture stirred for a further 40 min. A solution of with 1-chloromethyl-4-methyl-benzene(4.23 g, 30 mmol) in dimethylformamide (50 ml) was added dropwise with stirring. The resulting mixture was then stirred at room temperature for 12 h and poured into water (500 ml), yielding a white precipitate. The solid product was filtered off, washed with cold water and recrystallized from EtOH, giving crystals of (I). Yield: 4.89 g (90.2%); m.p. 390 K. Compound (I) (40 mg) was dissolved in a mixture of chloroform (5 ml) and ethanol (5 ml) and the solution was kept at room temperature for 18 d. Natural evaporation of the solution gave colourless crystals suitable for X-Ray analysis.

S3. Refinement

All H atoms were included in the riding model approximation with C—H distances = 0.93 (aromatic), 0.96 (methyl) and 0.97 (methene) Å, and with U_iso(H) = 1.2U_eq(C).

Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Figures

Fig. 1. A view of the molecular structure of (I). Displacement ellopsoids are drawn at the 30% probability level.

9-(4-Methylbenzyl)-9H-carbazole

Crystal data

C20H17N	Dx = 1.212 Mg m^−3
Mr = 271.35	Melting point: 390 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2354 reflections
a = 5.6128 (10) Å	θ = 2.6–24.7°
b = 13.627 (3) Å	µ = 0.07 mm^−1
c = 19.442 (4) Å	T = 294 K
V = 1487.0 (5) Å^3	Rod, colourless
Z = 4	0.24 × 0.20 × 0.10 mm
F(000) = 576

Data collection

Bruker SMART CCD area-detector diffractometer	1783 independent reflections
Radiation source: fine-focus sealed tube	1305 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
ϕ and ω scans	θmax = 26.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −7→6
Tmin = 0.978, Tmax = 0.993	k = −17→13
8438 measured reflections	l = −24→23

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.091	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0475P)^2 + 0.0342P] where P = (Fo^2 + 2Fc^2)/3
1783 reflections	(Δ/σ)max = 0.002
191 parameters	Δρmax = 0.11 e Å^−3
0 restraints	Δρmin = −0.16 e Å^−3

Special details

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 > 2σ(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 (Ų)

	x	y	z	Uiso*/Ueq
N1	0.0935 (3)	0.63116 (13)	0.76221 (8)	0.0475 (4)
C1	0.2777 (4)	0.56328 (15)	0.76494 (11)	0.0455 (5)
C2	0.3367 (4)	0.49680 (17)	0.81636 (12)	0.0580 (6)
H2	0.2489	0.4935	0.8569	0.070*
C3	0.5296 (5)	0.43580 (17)	0.80550 (13)	0.0648 (7)
H3	0.5713	0.3906	0.8392	0.078*
C4	0.6626 (5)	0.44044 (18)	0.74546 (13)	0.0652 (7)
H4	0.7916	0.3984	0.7395	0.078*
C5	0.6059 (4)	0.50639 (16)	0.69475 (12)	0.0561 (6)
H5	0.6961	0.5095	0.6547	0.067*
C6	0.4117 (4)	0.56873 (15)	0.70394 (10)	0.0442 (5)
C7	0.2999 (4)	0.64231 (15)	0.66166 (10)	0.0432 (5)
C8	0.3423 (5)	0.67858 (16)	0.59604 (10)	0.0555 (6)
H8	0.4713	0.6559	0.5706	0.067*
C9	0.1921 (5)	0.74821 (18)	0.56908 (11)	0.0643 (7)
H9	0.2199	0.7728	0.5252	0.077*
C10	0.0001 (5)	0.78210 (18)	0.60663 (12)	0.0644 (7)
H10	−0.1002	0.8287	0.5871	0.077*
C11	−0.0474 (4)	0.74901 (16)	0.67204 (11)	0.0546 (6)
H11	−0.1760	0.7730	0.6971	0.065*
C12	0.1038 (4)	0.67853 (15)	0.69914 (10)	0.0437 (5)
C13	−0.0820 (4)	0.64988 (18)	0.81569 (11)	0.0552 (6)
H13A	−0.1001	0.5910	0.8433	0.066*
H13B	−0.2344	0.6633	0.7941	0.066*
C14	−0.0200 (4)	0.73422 (16)	0.86244 (10)	0.0453 (5)
C15	0.1841 (4)	0.73371 (18)	0.90251 (11)	0.0567 (6)
H15	0.2884	0.6808	0.8997	0.068*
C16	0.2353 (5)	0.81027 (19)	0.94640 (12)	0.0618 (7)
H16	0.3730	0.8076	0.9729	0.074*
C17	0.0886 (5)	0.89026 (17)	0.95206 (11)	0.0580 (6)
C18	−0.1143 (5)	0.89149 (19)	0.91196 (12)	0.0671 (7)
H18	−0.2173	0.9448	0.9147	0.081*
C19	−0.1675 (4)	0.81479 (19)	0.86770 (11)	0.0606 (6)
H19	−0.3050	0.8177	0.8411	0.073*
C20	0.1479 (7)	0.9737 (2)	1.00032 (13)	0.0940 (10)
H20A	0.0644	1.0318	0.9861	0.141*
H20B	0.3163	0.9858	0.9993	0.141*
H20C	0.1005	0.9566	1.0462	0.141*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0424 (10)	0.0556 (11)	0.0444 (9)	−0.0032 (9)	0.0041 (9)	−0.0005 (8)
C1	0.0480 (12)	0.0420 (11)	0.0464 (11)	−0.0078 (10)	−0.0047 (11)	−0.0022 (10)
C2	0.0668 (16)	0.0522 (13)	0.0551 (13)	−0.0121 (13)	−0.0043 (13)	0.0054 (11)
C3	0.0764 (18)	0.0452 (13)	0.0727 (17)	−0.0016 (13)	−0.0216 (15)	0.0081 (13)
C4	0.0682 (17)	0.0504 (13)	0.0770 (17)	0.0106 (13)	−0.0178 (15)	−0.0106 (13)
C5	0.0558 (14)	0.0553 (13)	0.0573 (13)	0.0046 (12)	−0.0044 (13)	−0.0116 (12)
C6	0.0465 (12)	0.0428 (11)	0.0431 (11)	−0.0025 (10)	−0.0045 (10)	−0.0085 (9)
C7	0.0471 (12)	0.0429 (11)	0.0396 (11)	−0.0036 (10)	−0.0023 (10)	−0.0074 (9)
C8	0.0630 (15)	0.0614 (14)	0.0422 (12)	0.0014 (13)	0.0039 (11)	−0.0051 (11)
C9	0.0849 (18)	0.0639 (14)	0.0440 (12)	0.0068 (16)	−0.0061 (13)	0.0040 (12)
C10	0.0750 (18)	0.0607 (16)	0.0574 (14)	0.0112 (14)	−0.0205 (14)	−0.0018 (12)
C11	0.0510 (13)	0.0576 (13)	0.0550 (13)	0.0063 (12)	−0.0074 (11)	−0.0120 (12)
C12	0.0435 (11)	0.0451 (11)	0.0426 (11)	−0.0025 (10)	−0.0051 (10)	−0.0067 (10)
C13	0.0449 (12)	0.0698 (15)	0.0509 (12)	−0.0123 (12)	0.0096 (11)	−0.0050 (11)
C14	0.0388 (12)	0.0586 (14)	0.0385 (11)	−0.0063 (11)	0.0084 (10)	0.0020 (10)
C15	0.0494 (13)	0.0623 (15)	0.0583 (13)	0.0062 (12)	−0.0044 (12)	−0.0037 (12)
C16	0.0570 (15)	0.0775 (17)	0.0510 (13)	−0.0062 (14)	−0.0091 (12)	−0.0010 (13)
C17	0.0714 (17)	0.0572 (14)	0.0454 (13)	−0.0066 (14)	0.0088 (13)	0.0023 (11)
C18	0.0773 (18)	0.0608 (15)	0.0631 (15)	0.0150 (14)	0.0030 (15)	−0.0013 (13)
C19	0.0494 (14)	0.0770 (17)	0.0554 (13)	0.0119 (13)	−0.0026 (12)	0.0029 (13)
C20	0.129 (3)	0.0798 (19)	0.0731 (17)	−0.019 (2)	0.009 (2)	−0.0189 (16)

Geometric parameters (Å, º)

N1—C12	1.387 (3)	C10—H10	0.9300
N1—C1	1.388 (3)	C11—C12	1.386 (3)
N1—C13	1.455 (3)	C11—H11	0.9300
C1—C2	1.389 (3)	C13—C14	1.506 (3)
C1—C6	1.406 (3)	C13—H13A	0.9700
C2—C3	1.382 (3)	C13—H13B	0.9700
C2—H2	0.9300	C14—C19	1.379 (3)
C3—C4	1.387 (3)	C14—C15	1.386 (3)
C3—H3	0.9300	C15—C16	1.378 (3)
C4—C5	1.371 (3)	C15—H15	0.9300
C4—H4	0.9300	C16—C17	1.371 (3)
C5—C6	1.393 (3)	C16—H16	0.9300
C5—H5	0.9300	C17—C18	1.380 (4)
C6—C7	1.440 (3)	C17—C20	1.512 (3)
C7—C8	1.389 (3)	C18—C19	1.386 (3)
C7—C12	1.409 (3)	C18—H18	0.9300
C8—C9	1.373 (3)	C19—H19	0.9300
C8—H8	0.9300	C20—H20A	0.9600
C9—C10	1.381 (3)	C20—H20B	0.9600
C9—H9	0.9300	C20—H20C	0.9600
C10—C11	1.375 (3)
C12—N1—C1	108.24 (17)	C12—C11—H11	121.3
C12—N1—C13	125.33 (18)	C11—C12—N1	129.3 (2)
C1—N1—C13	126.43 (18)	C11—C12—C7	121.63 (19)
N1—C1—C2	129.8 (2)	N1—C12—C7	109.06 (18)
N1—C1—C6	109.32 (18)	N1—C13—C14	114.12 (18)
C2—C1—C6	120.9 (2)	N1—C13—H13A	108.7
C3—C2—C1	118.0 (2)	C14—C13—H13A	108.7
C3—C2—H2	121.0	N1—C13—H13B	108.7
C1—C2—H2	121.0	C14—C13—H13B	108.7
C2—C3—C4	121.5 (2)	H13A—C13—H13B	107.6
C2—C3—H3	119.2	C19—C14—C15	117.3 (2)
C4—C3—H3	119.2	C19—C14—C13	120.9 (2)
C5—C4—C3	120.7 (2)	C15—C14—C13	121.8 (2)
C5—C4—H4	119.7	C16—C15—C14	121.1 (2)
C3—C4—H4	119.7	C16—C15—H15	119.4
C4—C5—C6	119.3 (2)	C14—C15—H15	119.4
C4—C5—H5	120.4	C17—C16—C15	121.8 (2)
C6—C5—H5	120.4	C17—C16—H16	119.1
C5—C6—C1	119.6 (2)	C15—C16—H16	119.1
C5—C6—C7	133.8 (2)	C16—C17—C18	117.4 (2)
C1—C6—C7	106.56 (18)	C16—C17—C20	121.1 (3)
C8—C7—C12	119.0 (2)	C18—C17—C20	121.5 (3)
C8—C7—C6	134.2 (2)	C17—C18—C19	121.3 (2)
C12—C7—C6	106.79 (17)	C17—C18—H18	119.4
C9—C8—C7	119.4 (2)	C19—C18—H18	119.4
C9—C8—H8	120.3	C14—C19—C18	121.1 (2)
C7—C8—H8	120.3	C14—C19—H19	119.4
C8—C9—C10	120.5 (2)	C18—C19—H19	119.4
C8—C9—H9	119.7	C17—C20—H20A	109.5
C10—C9—H9	119.7	C17—C20—H20B	109.5
C11—C10—C9	122.0 (2)	H20A—C20—H20B	109.5
C11—C10—H10	119.0	C17—C20—H20C	109.5
C9—C10—H10	119.0	H20A—C20—H20C	109.5
C10—C11—C12	117.4 (2)	H20B—C20—H20C	109.5
C10—C11—H11	121.3
C12—N1—C1—C2	−178.0 (2)	C10—C11—C12—N1	−178.1 (2)
C13—N1—C1—C2	1.7 (3)	C10—C11—C12—C7	0.4 (3)
C12—N1—C1—C6	1.6 (2)	C1—N1—C12—C11	177.3 (2)
C13—N1—C1—C6	−178.70 (18)	C13—N1—C12—C11	−2.4 (3)
N1—C1—C2—C3	179.1 (2)	C1—N1—C12—C7	−1.4 (2)
C6—C1—C2—C3	−0.5 (3)	C13—N1—C12—C7	178.90 (17)
C1—C2—C3—C4	0.3 (3)	C8—C7—C12—C11	0.2 (3)
C2—C3—C4—C5	0.1 (4)	C6—C7—C12—C11	−178.14 (19)
C3—C4—C5—C6	−0.3 (4)	C8—C7—C12—N1	178.97 (18)
C4—C5—C6—C1	0.2 (3)	C6—C7—C12—N1	0.6 (2)
C4—C5—C6—C7	−177.5 (2)	C12—N1—C13—C14	−84.8 (2)
N1—C1—C6—C5	−179.44 (18)	C1—N1—C13—C14	95.5 (2)
C2—C1—C6—C5	0.2 (3)	N1—C13—C14—C19	119.8 (2)
N1—C1—C6—C7	−1.2 (2)	N1—C13—C14—C15	−61.2 (3)
C2—C1—C6—C7	178.51 (19)	C19—C14—C15—C16	0.8 (3)
C5—C6—C7—C8	0.3 (4)	C13—C14—C15—C16	−178.3 (2)
C1—C6—C7—C8	−177.6 (2)	C14—C15—C16—C17	−0.5 (3)
C5—C6—C7—C12	178.2 (2)	C15—C16—C17—C18	0.1 (3)
C1—C6—C7—C12	0.3 (2)	C15—C16—C17—C20	−179.8 (2)
C12—C7—C8—C9	−0.4 (3)	C16—C17—C18—C19	0.0 (4)
C6—C7—C8—C9	177.4 (2)	C20—C17—C18—C19	179.9 (2)
C7—C8—C9—C10	−0.1 (3)	C15—C14—C19—C18	−0.7 (3)
C8—C9—C10—C11	0.7 (4)	C13—C14—C19—C18	178.3 (2)
C9—C10—C11—C12	−0.9 (3)	C17—C18—C19—C14	0.3 (4)