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

The title compound, C₁₅H₁₃Br₂N, was synthesized by N-alkyl­ation of 2-bromo­propane with 3,6-dibromo-9H-carb­azole. The carbazole ring system is essentially planar, with a mean deviation of 0.01 Å. The isopropyl group is disordered over two positions across a pseudo-mirror plane perpendicular to the carbazole ring system.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.008 Å
• Disorder in main residue
• R factor = 0.050
• wR factor = 0.144
• Data-to-parameter ratio = 16.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT301_ALERT_3_C Main Residue  Disorder .........................      14.00 Perc.
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          8
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      15.70 Deg.
              C14B -N1   -C14A    1.555   1.555   1.555

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 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
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Bruker, 1997).

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

Crystal data

C15H13Br2N	Dx = 1.695 Mg m^−3
Mr = 367.08	Melting point: 400 K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3198 reflections
a = 16.896 (2) Å	θ = 2.3–26.0°
b = 8.3711 (10) Å	µ = 5.62 mm^−1
c = 20.345 (3) Å	T = 294 K
V = 2877.5 (6) Å^3	Rod, colourless
Z = 8	0.20 × 0.14 × 0.10 mm
F(000) = 1440

Data collection

Bruker SMART CCD area-detector diffractometer	3046 independent reflections
Radiation source: fine-focus sealed tube	1605 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.053
φ and ω scans	θmax = 26.8°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −21→21
Tmin = 0.398, Tmax = 0.570	k = −10→6
15500 measured reflections	l = −25→24

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.144	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0572P)^2 + 3.6671P] where P = (Fo^2 + 2Fc^2)/3
3046 reflections	(Δ/σ)max = 0.001
188 parameters	Δρmax = 0.98 e Å^−3
7 restraints	Δρmin = −0.62 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 > 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	Occ. (<1)
Br1	1.07930 (4)	0.07719 (9)	0.65085 (4)	0.1015 (3)
Br2	0.84497 (5)	0.36128 (10)	0.29306 (3)	0.1101 (4)
C1	0.8887 (3)	0.3639 (6)	0.4274 (2)	0.0586 (12)
H1	0.9189	0.2747	0.4167	0.070*
C2	0.9281 (3)	0.3792 (5)	0.5499 (2)	0.0517 (12)
C3	0.8880 (3)	0.4246 (6)	0.4908 (2)	0.0517 (11)
C4	0.8438 (3)	0.4392 (8)	0.3813 (3)	0.0711 (15)
N1	0.8540 (3)	0.6013 (5)	0.5713 (3)	0.0763 (14)
C14A	0.8212 (9)	0.7564 (14)	0.5956 (6)	0.102 (3)	0.59
H14A	0.7863	0.8054	0.5628	0.122*	0.59
C15A	0.7787 (8)	0.729 (2)	0.6583 (7)	0.082 (5)	0.59
H15A	0.7352	0.6575	0.6509	0.124*	0.59
H15B	0.7590	0.8291	0.6747	0.124*	0.59
H15C	0.8143	0.6832	0.6898	0.124*	0.59
C16A	0.8940 (10)	0.8668 (18)	0.6109 (10)	0.108 (7)	0.59
H16A	0.9230	0.8239	0.6474	0.162*	0.59
H16B	0.8757	0.9722	0.6215	0.162*	0.59
H16C	0.9279	0.8716	0.5730	0.162*	0.59
C14B	0.8334 (13)	0.7420 (19)	0.6118 (8)	0.102 (3)	0.41
H14B	0.8644	0.7322	0.6523	0.122*	0.41
C15B	0.7510 (12)	0.750 (4)	0.6323 (12)	0.100 (9)	0.41
H15D	0.7174	0.7466	0.5943	0.149*	0.41
H15E	0.7421	0.8478	0.6558	0.149*	0.41
H15F	0.7392	0.6609	0.6604	0.149*	0.41
C16B	0.8647 (15)	0.893 (2)	0.5765 (15)	0.100 (9)	0.41
H16D	0.9100	0.9333	0.5996	0.150*	0.41
H16E	0.8240	0.9731	0.5758	0.150*	0.41
H16F	0.8794	0.8663	0.5323	0.150*	0.41
C6	0.9058 (3)	0.4917 (6)	0.5982 (3)	0.0606 (13)
C7	0.8432 (3)	0.5619 (6)	0.5055 (3)	0.0658 (14)
C8	0.9796 (3)	0.2551 (6)	0.5655 (2)	0.0557 (12)
H8	0.9941	0.1803	0.5339	0.067*
C9	0.9868 (4)	0.3549 (8)	0.6760 (3)	0.0812 (17)
H9	1.0070	0.3449	0.7183	0.097*
C10	0.9361 (4)	0.4767 (8)	0.6618 (3)	0.0817 (18)
H10	0.9217	0.5494	0.6942	0.098*
C11	1.0086 (3)	0.2453 (7)	0.6279 (3)	0.0689 (15)
C12	0.7982 (3)	0.5724 (9)	0.3962 (4)	0.0875 (19)
H12	0.7676	0.6192	0.3635	0.105*
C13	0.7973 (3)	0.6360 (8)	0.4580 (4)	0.0883 (19)
H13	0.7671	0.7257	0.4678	0.106*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.1070 (5)	0.1007 (6)	0.0969 (5)	0.0081 (4)	−0.0247 (4)	0.0308 (4)
Br2	0.1246 (6)	0.1432 (7)	0.0624 (4)	−0.0353 (5)	−0.0218 (4)	0.0176 (4)
C1	0.055 (3)	0.066 (3)	0.055 (3)	−0.006 (2)	0.004 (2)	0.006 (3)
C2	0.054 (3)	0.045 (3)	0.056 (3)	−0.005 (2)	0.012 (2)	−0.004 (2)
C3	0.048 (2)	0.053 (3)	0.055 (3)	−0.004 (2)	0.006 (2)	0.004 (2)
C4	0.068 (3)	0.082 (4)	0.063 (3)	−0.015 (3)	−0.005 (3)	0.016 (3)
N1	0.076 (3)	0.055 (3)	0.097 (4)	0.009 (2)	0.025 (3)	−0.015 (3)
C14A	0.097 (6)	0.068 (5)	0.140 (8)	0.005 (4)	0.056 (6)	−0.029 (5)
C15A	0.070 (10)	0.079 (9)	0.098 (11)	0.019 (8)	0.031 (8)	−0.010 (8)
C16A	0.092 (12)	0.070 (10)	0.16 (2)	−0.018 (9)	0.038 (11)	−0.039 (11)
C14B	0.097 (6)	0.068 (5)	0.140 (8)	0.005 (4)	0.056 (6)	−0.029 (5)
C15B	0.064 (14)	0.097 (15)	0.14 (2)	0.029 (12)	0.033 (13)	0.008 (16)
C16B	0.088 (18)	0.058 (11)	0.15 (3)	−0.003 (10)	0.036 (15)	−0.010 (13)
C6	0.062 (3)	0.060 (3)	0.060 (3)	−0.013 (3)	0.015 (3)	−0.013 (3)
C7	0.053 (3)	0.058 (3)	0.087 (4)	0.002 (3)	0.016 (3)	0.000 (3)
C8	0.059 (3)	0.051 (3)	0.057 (3)	−0.002 (2)	0.006 (2)	0.001 (2)
C9	0.087 (4)	0.102 (5)	0.055 (3)	−0.016 (4)	−0.005 (3)	−0.004 (3)
C10	0.085 (4)	0.093 (5)	0.067 (4)	−0.020 (4)	0.018 (3)	−0.025 (3)
C11	0.068 (3)	0.077 (4)	0.061 (3)	−0.013 (3)	0.001 (3)	0.014 (3)
C12	0.068 (4)	0.093 (5)	0.101 (5)	−0.001 (4)	−0.018 (4)	0.036 (4)
C13	0.065 (4)	0.073 (4)	0.126 (6)	0.018 (3)	0.007 (4)	0.014 (4)

Geometric parameters (Å, º)

Br1—C11	1.903 (6)	C16A—H16C	0.9600
Br2—C4	1.910 (6)	C14B—C15B	1.454 (15)
C1—C4	1.360 (7)	C14B—C16B	1.546 (16)
C1—C3	1.387 (7)	C14B—H14B	0.9800
C1—H1	0.9300	C15B—H15D	0.9600
C2—C8	1.392 (6)	C15B—H15E	0.9600
C2—C6	1.411 (7)	C15B—H15F	0.9600
C2—C3	1.431 (7)	C16B—H16D	0.9600
C3—C7	1.408 (7)	C16B—H16E	0.9600
C4—C12	1.389 (9)	C16B—H16F	0.9600
N1—C6	1.382 (7)	C6—C10	1.397 (8)
N1—C7	1.391 (7)	C7—C13	1.385 (8)
N1—C14B	1.479 (14)	C8—C11	1.364 (7)
N1—C14A	1.496 (11)	C8—H8	0.9300
C14A—C15A	1.481 (13)	C9—C10	1.363 (9)
C14A—C16A	1.569 (13)	C9—C11	1.391 (8)
C14A—H14A	0.9800	C9—H9	0.9300
C15A—H15A	0.9600	C10—H10	0.9300
C15A—H15B	0.9600	C12—C13	1.365 (9)
C15A—H15C	0.9600	C12—H12	0.9300
C16A—H16A	0.9600	C13—H13	0.9300
C16A—H16B	0.9600
C4—C1—C3	117.8 (5)	C14B—C15B—H15F	109.5
C4—C1—H1	121.1	H15D—C15B—H15F	109.5
C3—C1—H1	121.1	H15E—C15B—H15F	109.5
C8—C2—C6	120.4 (5)	C14B—C16B—H16D	109.5
C8—C2—C3	133.3 (4)	C14B—C16B—H16E	109.5
C6—C2—C3	106.3 (4)	H16D—C16B—H16E	109.5
C1—C3—C7	120.1 (5)	C14B—C16B—H16F	109.5
C1—C3—C2	132.9 (5)	H16D—C16B—H16F	109.5
C7—C3—C2	107.0 (4)	H16E—C16B—H16F	109.5
C1—C4—C12	122.1 (6)	N1—C6—C10	131.2 (5)
C1—C4—Br2	118.9 (5)	N1—C6—C2	109.7 (5)
C12—C4—Br2	119.0 (5)	C10—C6—C2	119.1 (5)
C6—N1—C7	107.9 (4)	C13—C7—N1	129.7 (5)
C6—N1—C14B	117.2 (8)	C13—C7—C3	121.2 (6)
C7—N1—C14B	134.0 (8)	N1—C7—C3	109.1 (5)
C6—N1—C14A	132.9 (7)	C11—C8—C2	118.8 (5)
C7—N1—C14A	118.4 (6)	C11—C8—H8	120.6
C14B—N1—C14A	15.7 (8)	C2—C8—H8	120.6
C15A—C14A—N1	109.3 (10)	C10—C9—C11	120.7 (6)
C15A—C14A—C16A	107.5 (11)	C10—C9—H9	119.6
N1—C14A—C16A	106.6 (10)	C11—C9—H9	119.6
C15A—C14A—H14A	111.1	C9—C10—C6	119.6 (6)
N1—C14A—H14A	111.1	C9—C10—H10	120.2
C16A—C14A—H14A	111.1	C6—C10—H10	120.2
C15B—C14B—N1	115.0 (17)	C8—C11—C9	121.3 (5)
C15B—C14B—C16B	115.0 (15)	C8—C11—Br1	119.9 (4)
N1—C14B—C16B	108.2 (14)	C9—C11—Br1	118.8 (4)
C15B—C14B—H14B	106.0	C13—C12—C4	121.4 (6)
N1—C14B—H14B	106.0	C13—C12—H12	119.3
C16B—C14B—H14B	106.0	C4—C12—H12	119.3
C14B—C15B—H15D	109.5	C12—C13—C7	117.5 (6)
C14B—C15B—H15E	109.5	C12—C13—H13	121.3
H15D—C15B—H15E	109.5	C7—C13—H13	121.3