(3,6-Dibromo-9H-carbazol-9-yl)(phen­yl)methanone

The title compound, C₁₉H₁₁Br₂NO, was synthesized by N-alkyl­ation of benzoyl chloride with 3,6-dibromo-9H-carbazole. The carbazole ring system is essentially planar and makes a dihedral angle of 62.2 (1)° with the plane of the benzene ring. Weak C—H...Br hydrogen bonding occurs in the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C)= 0.006 Å
• R factor = 0.042
• wR factor = 0.116
• Data-to-parameter ratio = 13.3

checkCIF/PLATON results

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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: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

(3,6-Dibromo-9H-carbazol-9-yl)(phenyl)methanone

Crystal data

C19H11Br2NO	Z = 2
Mr = 429.11	F(000) = 420
Triclinic, P1	Dx = 1.793 Mg m^−3
Hall symbol: -P 1	Melting point = 483–484 K
a = 7.398 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.223 (3) Å	Cell parameters from 1944 reflections
c = 11.431 (4) Å	θ = 2.9–25.0°
α = 61.384 (4)°	µ = 5.10 mm^−1
β = 80.036 (5)°	T = 294 K
γ = 72.641 (5)°	Rod, colourless
V = 794.7 (4) Å^3	0.30 × 0.26 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer	2780 independent reflections
Radiation source: fine-focus sealed tube	2170 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
φ and ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −8→8
Tmin = 0.242, Tmax = 0.362	k = −10→13
4061 measured reflections	l = −13→13

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)] = 0.042	H-atom parameters constrained
wR(F^2) = 0.116	w = 1/[σ^2(Fo^2) + (0.0624P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.002
2780 reflections	Δρmax = 0.64 e Å^−3
209 parameters	Δρmin = −0.63 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.081 (4)

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	0.25133 (7)	1.00740 (5)	0.91158 (5)	0.0593 (2)
Br2	0.30606 (7)	0.13097 (5)	1.38699 (5)	0.0662 (2)
O1	0.1005 (5)	0.4341 (3)	0.7158 (3)	0.0614 (9)
N1	0.2153 (4)	0.5385 (3)	0.8036 (3)	0.0358 (7)
C1	0.2197 (5)	0.6618 (4)	0.8077 (4)	0.0340 (8)
C2	0.1881 (6)	0.8001 (4)	0.7088 (4)	0.0399 (9)
H2	0.1633	0.8238	0.6222	0.048*
C3	0.1947 (6)	0.9003 (4)	0.7432 (4)	0.0417 (9)
H3	0.1738	0.9935	0.6788	0.050*
C4	0.2323 (5)	0.8648 (4)	0.8730 (4)	0.0392 (9)
C5	0.2548 (5)	0.7300 (4)	0.9738 (4)	0.0387 (9)
H5	0.2754	0.7077	1.0607	0.046*
C6	0.2453 (5)	0.6287 (4)	0.9399 (3)	0.0325 (8)
C7	0.2548 (5)	0.4811 (4)	1.0196 (4)	0.0344 (8)
C8	0.2774 (5)	0.3929 (4)	1.1564 (4)	0.0385 (9)
H8	0.2907	0.4264	1.2139	0.046*
C9	0.2791 (6)	0.2555 (4)	1.2018 (4)	0.0434 (10)
C10	0.2593 (6)	0.2020 (4)	1.1177 (4)	0.0496 (11)
H10	0.2629	0.1076	1.1523	0.059*
C11	0.2345 (6)	0.2894 (4)	0.9841 (4)	0.0452 (10)
H11	0.2190	0.2556	0.9275	0.054*
C12	0.2330 (5)	0.4290 (4)	0.9351 (4)	0.0343 (8)
C13	0.1767 (6)	0.5241 (4)	0.6958 (4)	0.0410 (9)
C14	0.2415 (6)	0.6166 (4)	0.5600 (4)	0.0423 (9)
C15	0.4143 (6)	0.6492 (4)	0.5361 (4)	0.0471 (10)
H15	0.4888	0.6202	0.6072	0.056*
C16	0.4772 (7)	0.7249 (5)	0.4066 (4)	0.0567 (12)
H16	0.5945	0.7455	0.3910	0.068*
C17	0.3673 (8)	0.7695 (5)	0.3015 (5)	0.0630 (13)
H17	0.4092	0.8213	0.2149	0.076*
C18	0.1927 (8)	0.7373 (5)	0.3243 (5)	0.0656 (14)
H18	0.1173	0.7689	0.2530	0.079*
C19	0.1314 (7)	0.6585 (5)	0.4528 (4)	0.0525 (11)
H19	0.0174	0.6334	0.4678	0.063*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0803 (4)	0.0475 (3)	0.0699 (4)	−0.0202 (2)	−0.0008 (3)	−0.0402 (3)
Br2	0.0697 (4)	0.0614 (4)	0.0446 (3)	−0.0181 (2)	−0.0083 (2)	−0.0032 (2)
O1	0.081 (2)	0.074 (2)	0.0551 (18)	−0.0401 (18)	−0.0012 (17)	−0.0385 (17)
N1	0.0433 (19)	0.0364 (17)	0.0369 (17)	−0.0091 (13)	−0.0035 (14)	−0.0236 (14)
C1	0.035 (2)	0.035 (2)	0.039 (2)	−0.0083 (15)	−0.0005 (16)	−0.0229 (17)
C2	0.044 (2)	0.044 (2)	0.036 (2)	−0.0090 (17)	−0.0044 (18)	−0.0221 (18)
C3	0.048 (2)	0.033 (2)	0.042 (2)	−0.0094 (16)	0.0003 (19)	−0.0159 (17)
C4	0.042 (2)	0.040 (2)	0.046 (2)	−0.0100 (16)	0.0012 (18)	−0.0282 (18)
C5	0.044 (2)	0.045 (2)	0.036 (2)	−0.0081 (17)	−0.0025 (18)	−0.0271 (18)
C6	0.033 (2)	0.038 (2)	0.0326 (19)	−0.0056 (15)	−0.0028 (16)	−0.0223 (16)
C7	0.033 (2)	0.036 (2)	0.0376 (19)	−0.0039 (15)	−0.0026 (16)	−0.0210 (16)
C8	0.036 (2)	0.044 (2)	0.0334 (19)	−0.0054 (16)	−0.0046 (17)	−0.0177 (17)
C9	0.039 (2)	0.043 (2)	0.039 (2)	−0.0057 (17)	−0.0031 (18)	−0.0136 (18)
C10	0.053 (3)	0.034 (2)	0.054 (3)	−0.0097 (18)	0.000 (2)	−0.016 (2)
C11	0.053 (3)	0.039 (2)	0.052 (2)	−0.0124 (18)	0.001 (2)	−0.028 (2)
C12	0.037 (2)	0.034 (2)	0.0361 (19)	−0.0075 (15)	−0.0028 (16)	−0.0192 (16)
C13	0.045 (2)	0.047 (2)	0.044 (2)	−0.0087 (18)	−0.0046 (19)	−0.0314 (19)
C14	0.049 (3)	0.047 (2)	0.042 (2)	−0.0054 (18)	−0.0057 (19)	−0.0320 (19)
C15	0.051 (3)	0.053 (3)	0.045 (2)	−0.0086 (19)	−0.007 (2)	−0.030 (2)
C16	0.066 (3)	0.061 (3)	0.051 (3)	−0.023 (2)	0.007 (2)	−0.030 (2)
C17	0.078 (4)	0.060 (3)	0.044 (3)	−0.015 (2)	0.001 (2)	−0.020 (2)
C18	0.081 (4)	0.072 (3)	0.044 (3)	0.000 (3)	−0.018 (3)	−0.032 (2)
C19	0.051 (3)	0.067 (3)	0.052 (3)	−0.008 (2)	−0.009 (2)	−0.038 (2)

Geometric parameters (Å, º)

Br1—C4	1.900 (4)	C8—H8	0.9300
Br2—C9	1.903 (4)	C9—C10	1.400 (6)
O1—C13	1.210 (4)	C10—C11	1.372 (6)
N1—C13	1.402 (5)	C10—H10	0.9300
N1—C12	1.411 (5)	C11—C12	1.385 (5)
N1—C1	1.417 (4)	C11—H11	0.9300
C1—C2	1.391 (5)	C13—C14	1.488 (6)
C1—C6	1.406 (5)	C14—C15	1.380 (6)
C2—C3	1.373 (5)	C14—C19	1.396 (6)
C2—H2	0.9300	C15—C16	1.387 (6)
C3—C4	1.396 (6)	C15—H15	0.9300
C3—H3	0.9300	C16—C17	1.369 (6)
C4—C5	1.375 (5)	C16—H16	0.9300
C5—C6	1.387 (5)	C17—C18	1.392 (7)
C5—H5	0.9300	C17—H17	0.9300
C6—C7	1.444 (5)	C18—C19	1.383 (7)
C7—C12	1.397 (5)	C18—H18	0.9300
C7—C8	1.400 (5)	C19—H19	0.9300
C8—C9	1.368 (5)
C13—N1—C12	123.3 (3)	C11—C10—C9	119.7 (4)
C13—N1—C1	128.6 (3)	C11—C10—H10	120.2
C12—N1—C1	107.6 (3)	C9—C10—H10	120.2
C2—C1—C6	120.4 (3)	C10—C11—C12	118.9 (4)
C2—C1—N1	130.6 (3)	C10—C11—H11	120.6
C6—C1—N1	108.7 (3)	C12—C11—H11	120.6
C3—C2—C1	117.8 (3)	C11—C12—C7	121.0 (3)
C3—C2—H2	121.1	C11—C12—N1	130.2 (3)
C1—C2—H2	121.1	C7—C12—N1	108.8 (3)
C2—C3—C4	121.2 (4)	O1—C13—N1	119.8 (4)
C2—C3—H3	119.4	O1—C13—C14	122.1 (4)
C4—C3—H3	119.4	N1—C13—C14	118.0 (3)
C5—C4—C3	122.0 (4)	C15—C14—C19	119.6 (4)
C5—C4—Br1	119.1 (3)	C15—C14—C13	122.1 (3)
C3—C4—Br1	118.9 (3)	C19—C14—C13	117.9 (4)
C4—C5—C6	117.0 (3)	C14—C15—C16	120.3 (4)
C4—C5—H5	121.5	C14—C15—H15	119.9
C6—C5—H5	121.5	C16—C15—H15	119.9
C5—C6—C1	121.4 (3)	C17—C16—C15	120.2 (4)
C5—C6—C7	131.6 (3)	C17—C16—H16	119.9
C1—C6—C7	107.0 (3)	C15—C16—H16	119.9
C12—C7—C8	120.4 (3)	C16—C17—C18	120.0 (5)
C12—C7—C6	107.8 (3)	C16—C17—H17	120.0
C8—C7—C6	131.7 (3)	C18—C17—H17	120.0
C9—C8—C7	117.3 (3)	C19—C18—C17	120.1 (4)
C9—C8—H8	121.4	C19—C18—H18	120.0
C7—C8—H8	121.4	C17—C18—H18	120.0
C8—C9—C10	122.8 (4)	C18—C19—C14	119.7 (4)
C8—C9—Br2	119.2 (3)	C18—C19—H19	120.2
C10—C9—Br2	118.0 (3)	C14—C19—H19	120.2
C13—N1—C1—C2	0.0 (7)	C9—C10—C11—C12	1.1 (6)
C12—N1—C1—C2	−172.4 (4)	C10—C11—C12—C7	−0.5 (6)
C13—N1—C1—C6	174.0 (4)	C10—C11—C12—N1	178.2 (4)
C12—N1—C1—C6	1.6 (4)	C8—C7—C12—C11	−0.4 (6)
C6—C1—C2—C3	4.0 (5)	C6—C7—C12—C11	−179.5 (3)
N1—C1—C2—C3	177.4 (4)	C8—C7—C12—N1	−179.4 (3)
C1—C2—C3—C4	0.1 (6)	C6—C7—C12—N1	1.6 (4)
C2—C3—C4—C5	−3.4 (6)	C13—N1—C12—C11	6.3 (6)
C2—C3—C4—Br1	177.0 (3)	C1—N1—C12—C11	179.2 (4)
C3—C4—C5—C6	2.3 (6)	C13—N1—C12—C7	−174.9 (4)
Br1—C4—C5—C6	−178.1 (3)	C1—N1—C12—C7	−2.0 (4)
C4—C5—C6—C1	1.9 (5)	C12—N1—C13—O1	22.9 (6)
C4—C5—C6—C7	−177.1 (4)	C1—N1—C13—O1	−148.5 (4)
C2—C1—C6—C5	−5.1 (6)	C12—N1—C13—C14	−153.9 (4)
N1—C1—C6—C5	−179.9 (3)	C1—N1—C13—C14	34.8 (6)
C2—C1—C6—C7	174.1 (3)	O1—C13—C14—C15	−137.1 (5)
N1—C1—C6—C7	−0.6 (4)	N1—C13—C14—C15	39.5 (6)
C5—C6—C7—C12	178.6 (4)	O1—C13—C14—C19	36.0 (6)
C1—C6—C7—C12	−0.6 (4)	N1—C13—C14—C19	−147.4 (4)
C5—C6—C7—C8	−0.4 (7)	C19—C14—C15—C16	1.0 (6)
C1—C6—C7—C8	−179.5 (4)	C13—C14—C15—C16	174.0 (4)
C12—C7—C8—C9	0.7 (5)	C14—C15—C16—C17	0.8 (7)
C6—C7—C8—C9	179.5 (4)	C15—C16—C17—C18	−0.8 (8)
C7—C8—C9—C10	−0.1 (6)	C16—C17—C18—C19	−1.0 (8)
C7—C8—C9—Br2	−179.2 (3)	C17—C18—C19—C14	2.8 (8)
C8—C9—C10—C11	−0.8 (6)	C15—C14—C19—C18	−2.8 (7)
Br2—C9—C10—C11	178.3 (3)	C13—C14—C19—C18	−176.1 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···Br1^i	0.93	2.82	3.600 (6)	143

Symmetry code: (i) x, y−1, z.