3,6-Dibromo-9-hexyl-9H-carbazole

The title compound, C₁₈H₁₉Br₂N, was synthesized by N-alkyl­ation of 1-bromo­hexane with 3,6-dibromo-9H-carbazole. The carbazole ring system is essentially planar and the n-hexyl chain is in the fully extended conformation.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.009 Å
• R factor = 0.047
• wR factor = 0.117
• Data-to-parameter ratio = 17.5

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         10

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           26.37
           From the CIF: _reflns_number_total               3345
           Count of symmetry unique reflns         1816
           Completeness (_total/calc)            184.20%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1529
           Fraction of Friedel pairs measured     0.842
           Are heavy atom types Z>Si present        yes

   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
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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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.

3,6-Dibromo-9-hexyl-9H-carbazole

Crystal data

C18H19Br2N	Dx = 1.584 Mg m^−3
Mr = 409.16	Melting point: 374(1) K
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 2405 reflections
a = 20.337 (3) Å	θ = 2.2–21.8°
b = 4.5710 (6) Å	µ = 4.72 mm^−1
c = 18.456 (3) Å	T = 294 K
V = 1715.6 (4) Å^3	Rod, colourless
Z = 4	0.24 × 0.22 × 0.14 mm
F(000) = 816

Data collection

Bruker SMART-CCD area detector diffractometer	3345 independent reflections
Radiation source: fine-focus sealed tube	2056 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.080
φ and ω scans	θmax = 26.4°, θmin = 2.0°
Absorption correction: multi-scan SADABS (Bruker, 1997)	h = −25→19
Tmin = 0.320, Tmax = 0.517	k = −5→5
8839 measured reflections	l = −22→22

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.047	H-atom parameters constrained
wR(F^2) = 0.117	w = 1/[σ^2(Fo^2) + (0.05P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max = 0.005
3345 reflections	Δρmax = 0.57 e Å^−3
191 parameters	Δρmin = −0.44 e Å^−3
7 restraints	Absolute structure: Flack (1983), with 1529 Friedel Pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.006 (17)

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 > 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 (Ų)

	x	y	z	Uiso*/Ueq
Br1	1.07449 (3)	−0.08463 (19)	0.27357 (4)	0.0730 (3)
Br2	0.72081 (3)	−0.0554 (2)	0.00779 (5)	0.0862 (3)
N1	0.9882 (2)	0.5042 (11)	−0.0012 (3)	0.0475 (12)
C1	1.0487 (3)	0.0995 (16)	0.1842 (3)	0.0535 (17)
C2	1.0941 (3)	0.2842 (17)	0.1520 (4)	0.0580 (18)
H2	1.1354	0.3114	0.1726	0.070*
C3	1.0774 (3)	0.4264 (17)	0.0892 (4)	0.0566 (18)
H3	1.1073	0.5503	0.0665	0.068*
C4	1.0159 (3)	0.3827 (14)	0.0604 (3)	0.0445 (16)
C5	0.9253 (3)	0.3881 (13)	−0.0095 (3)	0.0427 (15)
C6	0.8782 (4)	0.4429 (16)	−0.0620 (3)	0.0558 (17)
H6	0.8867	0.5700	−0.1002	0.067*
C7	0.8187 (3)	0.3047 (18)	−0.0560 (4)	0.0608 (19)
H7	0.7866	0.3361	−0.0911	0.073*
C8	0.8056 (3)	0.1220 (14)	0.0006 (4)	0.0563 (17)
C9	0.8514 (3)	0.0550 (15)	0.0525 (3)	0.0499 (16)
H9	0.8424	−0.0803	0.0888	0.060*
C10	0.9129 (2)	0.2004 (14)	0.0486 (3)	0.0403 (14)
C11	0.9707 (3)	0.1933 (14)	0.0926 (3)	0.0399 (14)
C12	0.9878 (3)	0.0433 (15)	0.1569 (3)	0.0476 (16)
H12	0.9590	−0.0864	0.1793	0.057*
C13	1.0213 (3)	0.6970 (15)	−0.0518 (4)	0.0540 (17)
H13A	1.0476	0.8374	−0.0251	0.065*
H13B	0.9887	0.8048	−0.0794	0.065*
C14	1.0657 (4)	0.5281 (15)	−0.1041 (4)	0.0516 (17)
H14A	1.0967	0.4126	−0.0762	0.062*
H14B	1.0389	0.3941	−0.1322	0.062*
C15	1.1030 (3)	0.7224 (16)	−0.1549 (3)	0.0542 (17)
H15A	1.1271	0.8660	−0.1268	0.065*
H15B	1.0719	0.8272	−0.1852	0.065*
C16	1.1506 (4)	0.5608 (16)	−0.2029 (4)	0.064 (2)
H16A	1.1785	0.4410	−0.1724	0.077*
H16B	1.1256	0.4296	−0.2337	0.077*
C17	1.1936 (4)	0.743 (2)	−0.2501 (4)	0.080 (2)
H17A	1.1655	0.8579	−0.2817	0.096*
H17B	1.2172	0.8797	−0.2194	0.096*
C18	1.2415 (5)	0.591 (2)	−0.2950 (5)	0.095 (3)
H18A	1.2674	0.4631	−0.2653	0.143*
H18B	1.2697	0.7315	−0.3181	0.143*
H18C	1.2189	0.4787	−0.3312	0.143*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0792 (5)	0.0922 (6)	0.0477 (4)	0.0189 (4)	−0.0084 (4)	−0.0021 (6)
Br2	0.0500 (4)	0.0999 (7)	0.1088 (7)	−0.0088 (4)	−0.0130 (4)	−0.0147 (7)
N1	0.056 (3)	0.043 (3)	0.044 (3)	0.001 (2)	0.014 (3)	0.006 (3)
C1	0.057 (4)	0.065 (5)	0.039 (3)	0.007 (4)	−0.002 (3)	−0.011 (3)
C2	0.050 (4)	0.067 (5)	0.056 (4)	0.007 (4)	−0.009 (3)	−0.013 (4)
C3	0.054 (4)	0.050 (5)	0.066 (5)	−0.008 (3)	0.009 (4)	−0.014 (4)
C4	0.049 (4)	0.043 (4)	0.043 (4)	−0.003 (3)	0.005 (3)	−0.011 (3)
C5	0.045 (3)	0.041 (4)	0.043 (3)	0.006 (3)	0.010 (3)	−0.008 (3)
C6	0.069 (5)	0.054 (4)	0.045 (4)	0.020 (4)	0.003 (3)	−0.008 (3)
C7	0.058 (4)	0.076 (5)	0.048 (4)	0.021 (4)	−0.009 (3)	−0.013 (4)
C8	0.050 (3)	0.061 (5)	0.058 (4)	0.004 (3)	−0.010 (3)	−0.016 (4)
C9	0.047 (3)	0.051 (4)	0.051 (4)	0.000 (3)	0.009 (3)	−0.010 (3)
C10	0.039 (3)	0.044 (4)	0.038 (3)	0.003 (3)	0.007 (2)	−0.007 (3)
C11	0.043 (3)	0.043 (4)	0.034 (3)	0.000 (3)	0.009 (3)	−0.003 (3)
C12	0.048 (3)	0.048 (4)	0.046 (4)	−0.004 (3)	0.012 (3)	−0.007 (3)
C13	0.076 (4)	0.036 (4)	0.051 (4)	0.003 (3)	0.014 (3)	0.000 (3)
C14	0.067 (4)	0.035 (4)	0.053 (4)	−0.006 (3)	0.017 (3)	−0.002 (3)
C15	0.057 (4)	0.056 (5)	0.050 (4)	0.003 (3)	0.009 (3)	0.004 (4)
C16	0.067 (4)	0.056 (5)	0.071 (5)	0.001 (4)	0.019 (4)	0.000 (4)
C17	0.092 (5)	0.075 (6)	0.073 (5)	0.013 (5)	0.035 (4)	0.017 (4)
C18	0.094 (5)	0.090 (6)	0.101 (6)	0.013 (5)	0.043 (5)	0.006 (5)

Geometric parameters (Å, º)

Br1—C1	1.923 (7)	C10—C11	1.430 (8)
Br2—C8	1.911 (6)	C11—C12	1.414 (9)
N1—C4	1.385 (9)	C12—H12	0.9300
N1—C5	1.395 (7)	C13—C14	1.530 (9)
N1—C13	1.450 (8)	C13—H13A	0.9700
C1—C12	1.363 (9)	C13—H13B	0.9700
C1—C2	1.386 (10)	C14—C15	1.499 (9)
C2—C3	1.370 (10)	C14—H14A	0.9700
C2—H2	0.9300	C14—H14B	0.9700
C3—C4	1.375 (9)	C15—C16	1.505 (9)
C3—H3	0.9300	C15—H15A	0.9700
C4—C11	1.394 (9)	C15—H15B	0.9700
C5—C6	1.384 (9)	C16—C17	1.490 (10)
C5—C10	1.397 (8)	C16—H16A	0.9700
C6—C7	1.370 (10)	C16—H16B	0.9700
C6—H6	0.9300	C17—C18	1.456 (11)
C7—C8	1.363 (10)	C17—H17A	0.9700
C7—H7	0.9300	C17—H17B	0.9700
C8—C9	1.369 (9)	C18—H18A	0.9600
C9—C10	1.418 (8)	C18—H18B	0.9600
C9—H9	0.9300	C18—H18C	0.9600
C4—N1—C5	108.1 (5)	C11—C12—H12	121.9
C4—N1—C13	125.8 (5)	N1—C13—C14	111.9 (5)
C5—N1—C13	125.9 (6)	N1—C13—H13A	109.2
C12—C1—C2	124.2 (6)	C14—C13—H13A	109.2
C12—C1—Br1	118.8 (5)	N1—C13—H13B	109.2
C2—C1—Br1	117.0 (5)	C14—C13—H13B	109.2
C3—C2—C1	119.2 (6)	H13A—C13—H13B	107.9
C3—C2—H2	120.4	C15—C14—C13	113.2 (6)
C1—C2—H2	120.4	C15—C14—H14A	108.9
C2—C3—C4	118.9 (7)	C13—C14—H14A	108.9
C2—C3—H3	120.5	C15—C14—H14B	108.9
C4—C3—H3	120.6	C13—C14—H14B	108.9
C3—C4—N1	129.0 (6)	H14A—C14—H14B	107.7
C3—C4—C11	121.7 (6)	C14—C15—C16	113.8 (6)
N1—C4—C11	109.3 (5)	C14—C15—H15A	108.8
C6—C5—C10	121.6 (6)	C16—C15—H15A	108.8
C6—C5—N1	130.0 (6)	C14—C15—H15B	108.8
C10—C5—N1	108.3 (5)	C16—C15—H15B	108.8
C7—C6—C5	118.1 (7)	H15A—C15—H15B	107.7
C7—C6—H6	121.0	C17—C16—C15	116.5 (7)
C5—C6—H6	121.0	C17—C16—H16A	108.2
C8—C7—C6	121.1 (6)	C15—C16—H16A	108.2
C8—C7—H7	119.5	C17—C16—H16B	108.2
C6—C7—H7	119.5	C15—C16—H16B	108.2
C7—C8—C9	122.7 (6)	H16A—C16—H16B	107.3
C7—C8—Br2	119.3 (5)	C18—C17—C16	117.3 (8)
C9—C8—Br2	118.0 (6)	C18—C17—H17A	108.0
C8—C9—C10	117.3 (6)	C16—C17—H17A	108.0
C8—C9—H9	121.3	C18—C17—H17B	108.0
C10—C9—H9	121.3	C16—C17—H17B	108.0
C5—C10—C9	119.0 (5)	H17A—C17—H17B	107.2
C5—C10—C11	107.5 (5)	C17—C18—H18A	109.5
C9—C10—C11	133.4 (6)	C17—C18—H18B	109.5
C4—C11—C12	119.8 (5)	H18A—C18—H18B	109.5
C4—C11—C10	106.7 (5)	C17—C18—H18C	109.5
C12—C11—C10	133.5 (5)	H18A—C18—H18C	109.5
C1—C12—C11	116.2 (6)	H18B—C18—H18C	109.5
C1—C12—H12	121.9
C12—C1—C2—C3	1.2 (10)	C6—C5—C10—C11	−179.6 (5)
Br1—C1—C2—C3	−178.3 (5)	N1—C5—C10—C11	−2.0 (6)
C1—C2—C3—C4	0.4 (10)	C8—C9—C10—C5	−3.9 (8)
C2—C3—C4—N1	179.2 (6)	C8—C9—C10—C11	178.5 (6)
C2—C3—C4—C11	−1.4 (10)	C3—C4—C11—C12	0.7 (10)
C5—N1—C4—C3	178.4 (6)	N1—C4—C11—C12	−179.7 (5)
C13—N1—C4—C3	3.7 (10)	C3—C4—C11—C10	−179.7 (6)
C5—N1—C4—C11	−1.1 (6)	N1—C4—C11—C10	−0.2 (7)
C13—N1—C4—C11	−175.8 (6)	C5—C10—C11—C4	1.3 (7)
C4—N1—C5—C6	179.2 (6)	C9—C10—C11—C4	179.1 (6)
C13—N1—C5—C6	−6.0 (10)	C5—C10—C11—C12	−179.2 (6)
C4—N1—C5—C10	1.9 (6)	C9—C10—C11—C12	−1.4 (12)
C13—N1—C5—C10	176.6 (6)	C2—C1—C12—C11	−1.9 (9)
C10—C5—C6—C7	−0.7 (9)	Br1—C1—C12—C11	177.7 (4)
N1—C5—C6—C7	−177.7 (6)	C4—C11—C12—C1	0.9 (9)
C5—C6—C7—C8	1.0 (10)	C10—C11—C12—C1	−178.5 (6)
C6—C7—C8—C9	−3.0 (10)	C4—N1—C13—C14	79.1 (8)
C6—C7—C8—Br2	178.1 (5)	C5—N1—C13—C14	−94.7 (7)
C7—C8—C9—C10	4.4 (9)	N1—C13—C14—C15	−177.3 (6)
Br2—C8—C9—C10	−176.7 (4)	C13—C14—C15—C16	175.8 (6)
C6—C5—C10—C9	2.3 (8)	C14—C15—C16—C17	−174.7 (7)
N1—C5—C10—C9	179.8 (5)	C15—C16—C17—C18	177.9 (8)