6-Bromo-2-(3-phenyl-allyl-idene)-2,3,4,9-tetra-hydro-1H-carbazol-1-one.

Mol-ecules of the title compound, C(21)H(16)BrNO, are linked through pairs of N-H⋯O inter-molecular hydrogen bonds into centrosymmetric R(2) (2)(10) dimers. One of the C atoms of the cyclohex-2-enone ring is disordered with refined occupancies of 0.61 (2) and 0.39 (2).

Related literature

For the biological activity of carbazole derivatives, see: Shufen et al. (1995 ▶); Magnus et al. (1992 ▶); Abraham (1975 ▶); Saxton (1983 ▶); Phillipson & Zenk (1980 ▶); Bergman & Pelcman (1990 ▶); Bonesi et al. (2004 ▶); Chakraborty et al. (1965 ▶); Kirtikar & Basu (1933 ▶); Chakraborty et al. (1973 ▶); Knolker & Reddy, 2002 ▶. For puckering parameters, see: Cremer & Pople (1975 ▶). For asymmetry parameters, see: Nardelli (1983 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C21H16BrNO

M = 378.26

Monoclinic,

a = 17.3682 (7) Å

b = 14.9974 (8) Å

c = 6.6861 (3) Å

β = 92.226 (2)°

V = 1740.27 (14) Å3

Z = 4

Mo Kα radiation

μ = 2.37 mm−1

T = 293 K

0.20 × 0.17 × 0.16 mm

Data collection

Bruker SMART APEX CCD detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T min = 0.629, T max = 0.685

16684 measured reflections

4319 independent reflections

2158 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.137

S = 0.97

4319 reflections

231 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.46 e Å−3

Δρmin = −0.55 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT-Plus (Bruker, 1998 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811046563/bt5677sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811046563/bt5677Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811046563/bt5677Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C21H16BrNO	F(000) = 768
Mr = 378.26	Dx = 1.444 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2134 reflections
a = 17.3682 (7) Å	θ = 1.2–28.3°
b = 14.9974 (8) Å	µ = 2.37 mm−1
c = 6.6861 (3) Å	T = 293 K
β = 92.226 (2)°	Block, yellow
V = 1740.27 (14) Å3	0.20 × 0.17 × 0.16 mm
Z = 4

Bruker SMART APEX CCD detector diffractometer	4319 independent reflections
Radiation source: fine-focus sealed tube	2158 reflections with I > 2σ(I)
graphite	Rint = 0.044
ω scans	θmax = 28.3°, θmin = 1.2°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −23→23
Tmin = 0.629, Tmax = 0.685	k = −18→20
16684 measured reflections	l = −8→8

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137	H atoms treated by a mixture of independent and constrained refinement
S = 0.97	w = 1/[σ2(Fo2) + (0.0592P)2 + 0.6068P] where P = (Fo2 + 2Fc2)/3
4319 reflections	(Δ/σ)max < 0.001
231 parameters	Δρmax = 0.46 e Å−3
0 restraints	Δρmin = −0.55 e Å−3

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
Br1	0.39020 (2)	0.32240 (3)	0.51370 (6)	0.1026 (2)
O1	−0.08065 (12)	0.45133 (15)	0.1631 (3)	0.0688 (6)
N1	0.08292 (14)	0.42507 (17)	0.1535 (3)	0.0552 (6)
H1	0.0713 (17)	0.458 (2)	0.059 (4)	0.067 (9)*
C2	0.15712 (17)	0.40282 (18)	0.2075 (4)	0.0528 (7)
C3	0.22410 (18)	0.4135 (2)	0.1039 (4)	0.0641 (8)
H3	0.2229	0.4378	−0.0242	0.077*
C4	0.29216 (19)	0.3873 (2)	0.1963 (5)	0.0675 (8)
H4	0.3381	0.3937	0.1306	0.081*
C5	0.2929 (2)	0.3509 (2)	0.3901 (5)	0.0692 (9)
C6	0.22789 (19)	0.3375 (2)	0.4921 (4)	0.0622 (8)
H6	0.2299	0.3118	0.6187	0.075*
C7	0.15750 (17)	0.36386 (18)	0.4003 (4)	0.0505 (7)
C8	0.08023 (17)	0.36309 (18)	0.4592 (3)	0.0485 (6)
C9	0.04470 (19)	0.3290 (2)	0.6440 (4)	0.0658 (8)
H9A	0.0487	0.2645	0.6453	0.079*	0.61 (2)
H9B	0.0743	0.3513	0.7595	0.079*	0.61 (2)
H9C	0.0547	0.3712	0.7519	0.079*	0.39 (2)
H9D	0.0691	0.2730	0.6823	0.079*	0.39 (2)
C11	−0.08446 (18)	0.38062 (19)	0.4825 (4)	0.0538 (7)
C12	−0.04532 (17)	0.41447 (18)	0.3044 (3)	0.0506 (7)
C13	0.03659 (16)	0.40161 (17)	0.3067 (3)	0.0477 (6)
C14	−0.15949 (18)	0.3978 (2)	0.4961 (4)	0.0586 (7)
H14	−0.1826	0.4283	0.3886	0.070*
C15	−0.20892 (18)	0.3753 (2)	0.6550 (4)	0.0631 (8)
H15	−0.1887	0.3416	0.7613	0.076*
C16	−0.28207 (19)	0.4001 (2)	0.6583 (4)	0.0676 (8)
H16	−0.3011	0.4311	0.5464	0.081*
C17	−0.33642 (18)	0.3850 (2)	0.8155 (5)	0.0658 (8)
C18	−0.3143 (2)	0.3524 (2)	1.0019 (5)	0.0780 (10)
H18	−0.2625	0.3403	1.0313	0.094*
C19	−0.3677 (3)	0.3376 (3)	1.1451 (6)	0.0984 (13)
H19	−0.3521	0.3145	1.2692	0.118*
C20	−0.4435 (3)	0.3568 (3)	1.1050 (8)	0.1123 (16)
H20	−0.4795	0.3470	1.2019	0.135*
C21	−0.4661 (2)	0.3902 (4)	0.9231 (8)	0.1155 (16)
H21	−0.5178	0.4033	0.8962	0.139*
C22	−0.4137 (2)	0.4048 (3)	0.7794 (6)	0.0882 (11)
H22	−0.4300	0.4282	0.6561	0.106*
C10A	−0.0342 (11)	0.3529 (15)	0.665 (2)	0.058 (4)	0.39 (2)
H10A	−0.0353	0.4016	0.7602	0.069*	0.39 (2)
H10B	−0.0594	0.3026	0.7258	0.069*	0.39 (2)
C10B	−0.0401 (7)	0.3148 (9)	0.6188 (17)	0.059 (2)	0.61 (2)
H10C	−0.0619	0.3169	0.7501	0.071*	0.61 (2)
H10D	−0.0487	0.2551	0.5663	0.071*	0.61 (2)

	U11	U22	U33	U12	U13	U23
Br1	0.0700 (3)	0.1349 (5)	0.1014 (3)	−0.0016 (2)	−0.0135 (2)	0.0210 (2)
O1	0.0752 (13)	0.0818 (16)	0.0491 (10)	0.0044 (11)	−0.0026 (9)	0.0253 (10)
N1	0.0740 (16)	0.0542 (16)	0.0373 (11)	0.0027 (13)	0.0008 (11)	0.0120 (11)
C2	0.0742 (19)	0.0405 (16)	0.0434 (13)	0.0007 (14)	−0.0004 (13)	0.0012 (12)
C3	0.082 (2)	0.060 (2)	0.0505 (15)	−0.0032 (17)	0.0076 (15)	0.0044 (14)
C4	0.071 (2)	0.064 (2)	0.0688 (19)	−0.0054 (17)	0.0094 (15)	0.0014 (16)
C5	0.073 (2)	0.064 (2)	0.070 (2)	−0.0028 (16)	−0.0075 (17)	0.0020 (16)
C6	0.074 (2)	0.062 (2)	0.0499 (15)	−0.0001 (16)	−0.0078 (14)	0.0063 (14)
C7	0.0710 (18)	0.0384 (16)	0.0417 (13)	−0.0026 (13)	−0.0026 (12)	0.0030 (11)
C8	0.0729 (18)	0.0351 (15)	0.0372 (12)	−0.0008 (13)	−0.0034 (12)	−0.0007 (11)
C9	0.082 (2)	0.071 (2)	0.0438 (15)	−0.0037 (18)	−0.0009 (14)	0.0188 (14)
C11	0.0754 (19)	0.0448 (17)	0.0409 (13)	0.0034 (15)	0.0012 (12)	0.0033 (12)
C12	0.0739 (18)	0.0415 (16)	0.0363 (12)	0.0008 (14)	0.0002 (12)	0.0021 (11)
C13	0.0715 (18)	0.0374 (15)	0.0343 (12)	−0.0006 (13)	0.0028 (12)	0.0011 (11)
C14	0.075 (2)	0.0493 (18)	0.0510 (15)	0.0002 (15)	−0.0005 (14)	0.0049 (13)
C15	0.074 (2)	0.061 (2)	0.0544 (16)	−0.0034 (16)	0.0019 (14)	0.0079 (14)
C16	0.076 (2)	0.064 (2)	0.0621 (18)	−0.0054 (17)	−0.0012 (15)	0.0070 (15)
C17	0.069 (2)	0.056 (2)	0.0716 (19)	−0.0089 (16)	0.0036 (16)	−0.0021 (16)
C18	0.086 (2)	0.075 (2)	0.074 (2)	−0.0008 (19)	0.0086 (18)	0.0047 (18)
C19	0.132 (4)	0.091 (3)	0.074 (2)	−0.016 (3)	0.019 (3)	0.006 (2)
C20	0.105 (4)	0.130 (4)	0.105 (3)	−0.033 (3)	0.037 (3)	−0.021 (3)
C21	0.070 (2)	0.158 (5)	0.119 (4)	−0.018 (3)	0.014 (3)	−0.026 (3)
C22	0.073 (2)	0.100 (3)	0.091 (2)	−0.006 (2)	−0.001 (2)	−0.005 (2)
C10A	0.084 (7)	0.049 (10)	0.041 (6)	0.023 (8)	0.017 (5)	0.013 (5)
C10B	0.088 (4)	0.048 (6)	0.042 (4)	0.006 (5)	0.009 (3)	0.010 (3)

Br1—C5	1.900 (3)	C11—C10B	1.532 (11)
O1—C12	1.237 (3)	C11—C10A	1.529 (16)
N1—C2	1.366 (4)	C12—C13	1.435 (4)
N1—C13	1.373 (3)	C14—C15	1.432 (4)
N1—H1	0.82 (3)	C14—H14	0.9300
C2—C3	1.386 (4)	C15—C16	1.325 (4)
C2—C7	1.415 (4)	C15—H15	0.9300
C3—C4	1.370 (4)	C16—C17	1.458 (4)
C3—H3	0.9300	C16—H16	0.9300
C4—C5	1.406 (4)	C17—C18	1.379 (4)
C4—H4	0.9300	C17—C22	1.387 (4)
C5—C6	1.357 (5)	C18—C19	1.377 (5)
C6—C7	1.403 (4)	C18—H18	0.9300
C6—H6	0.9300	C19—C20	1.363 (6)
C7—C8	1.413 (4)	C19—H19	0.9300
C8—C13	1.374 (4)	C20—C21	1.359 (6)
C8—C9	1.492 (4)	C20—H20	0.9300
C9—C10A	1.429 (17)	C21—C22	1.366 (5)
C9—C10B	1.491 (12)	C21—H21	0.9300
C9—H9A	0.9700	C22—H22	0.9300
C9—H9B	0.9700	C10A—H10A	0.9700
C9—H9C	0.9700	C10A—H10B	0.9700
C9—H9D	0.9700	C10B—H10C	0.9700
C11—C14	1.335 (4)	C10B—H10D	0.9700
C11—C12	1.483 (4)
C2—N1—C13	108.3 (2)	C14—C11—C10A	121.7 (6)
C2—N1—H1	123 (2)	C12—C11—C10A	117.9 (7)
C13—N1—H1	127 (2)	C10B—C11—C10A	24.7 (5)
N1—C2—C3	129.9 (2)	O1—C12—C13	122.0 (2)
N1—C2—C7	108.2 (2)	O1—C12—C11	122.5 (3)
C3—C2—C7	121.9 (3)	C13—C12—C11	115.5 (2)
C4—C3—C2	117.9 (3)	N1—C13—C8	109.8 (2)
C4—C3—H3	121.1	N1—C13—C12	124.6 (2)
C2—C3—H3	121.1	C8—C13—C12	125.6 (2)
C3—C4—C5	120.3 (3)	C11—C14—C15	128.3 (3)
C3—C4—H4	119.9	C11—C14—H14	115.8
C5—C4—H4	119.9	C15—C14—H14	115.8
C6—C5—C4	122.8 (3)	C16—C15—C14	123.3 (3)
C6—C5—Br1	119.5 (2)	C16—C15—H15	118.3
C4—C5—Br1	117.7 (3)	C14—C15—H15	118.3
C5—C6—C7	117.9 (3)	C15—C16—C17	128.1 (3)
C5—C6—H6	121.1	C15—C16—H16	116.0
C7—C6—H6	121.1	C17—C16—H16	116.0
C6—C7—C8	134.2 (2)	C18—C17—C22	117.9 (3)
C6—C7—C2	119.2 (3)	C18—C17—C16	122.7 (3)
C8—C7—C2	106.6 (2)	C22—C17—C16	119.4 (3)
C13—C8—C7	107.0 (2)	C19—C18—C17	120.9 (4)
C13—C8—C9	121.6 (3)	C19—C18—H18	119.6
C7—C8—C9	131.4 (2)	C17—C18—H18	119.6
C10A—C9—C8	115.1 (6)	C20—C19—C18	120.1 (4)
C10A—C9—C10B	25.8 (6)	C20—C19—H19	120.0
C8—C9—C10B	113.2 (4)	C18—C19—H19	120.0
C10A—C9—H9A	108.5	C21—C20—C19	119.8 (4)
C8—C9—H9A	108.5	C21—C20—H20	120.1
C10B—C9—H9A	85.8	C19—C20—H20	120.1
C10A—C9—H9B	108.5	C20—C21—C22	120.7 (4)
C8—C9—H9B	108.5	C20—C21—H21	119.6
C10B—C9—H9B	129.1	C22—C21—H21	119.6
H9A—C9—H9B	107.5	C21—C22—C17	120.7 (4)
C10A—C9—H9C	84.7	C21—C22—H22	119.7
C8—C9—H9C	108.9	C17—C22—H22	119.7
C10B—C9—H9C	108.9	C9—C10A—C11	120.7 (9)
H9A—C9—H9C	129.3	C9—C10A—H10A	107.2
H9B—C9—H9C	27.1	C11—C10A—H10A	107.2
C10A—C9—H9D	127.0	C9—C10A—H10B	107.2
C8—C9—H9D	108.9	C11—C10A—H10B	107.2
C10B—C9—H9D	108.9	H10A—C10A—H10B	106.8
H9A—C9—H9D	26.4	C9—C10B—C11	116.5 (7)
H9B—C9—H9D	82.8	C9—C10B—H10C	108.2
H9C—C9—H9D	107.8	C11—C10B—H10C	108.2
C14—C11—C12	117.9 (2)	C9—C10B—H10D	108.2
C14—C11—C10B	123.6 (5)	C11—C10B—H10D	108.2
C12—C11—C10B	117.6 (5)	H10C—C10B—H10D	107.3
C13—N1—C2—C3	−179.7 (3)	C9—C8—C13—N1	−178.6 (3)
C13—N1—C2—C7	0.2 (3)	C7—C8—C13—C12	−179.9 (3)
N1—C2—C3—C4	178.2 (3)	C9—C8—C13—C12	0.5 (4)
C7—C2—C3—C4	−1.8 (4)	O1—C12—C13—N1	−2.5 (4)
C2—C3—C4—C5	0.0 (5)	C11—C12—C13—N1	177.5 (2)
C3—C4—C5—C6	1.8 (5)	O1—C12—C13—C8	178.6 (3)
C3—C4—C5—Br1	−176.5 (2)	C11—C12—C13—C8	−1.5 (4)
C4—C5—C6—C7	−1.8 (5)	C12—C11—C14—C15	−177.5 (3)
Br1—C5—C6—C7	176.6 (2)	C10B—C11—C14—C15	13.7 (8)
C5—C6—C7—C8	−178.1 (3)	C10A—C11—C14—C15	−15.7 (12)
C5—C6—C7—C2	0.0 (4)	C11—C14—C15—C16	176.1 (3)
N1—C2—C7—C6	−178.1 (3)	C14—C15—C16—C17	−176.8 (3)
C3—C2—C7—C6	1.8 (4)	C15—C16—C17—C18	10.0 (6)
N1—C2—C7—C8	0.4 (3)	C15—C16—C17—C22	−170.7 (4)
C3—C2—C7—C8	−179.6 (3)	C22—C17—C18—C19	1.9 (5)
C6—C7—C8—C13	177.4 (3)	C16—C17—C18—C19	−178.8 (3)
C2—C7—C8—C13	−0.9 (3)	C17—C18—C19—C20	−1.3 (6)
C6—C7—C8—C9	−3.1 (5)	C18—C19—C20—C21	0.3 (7)
C2—C7—C8—C9	178.7 (3)	C19—C20—C21—C22	0.1 (8)
C13—C8—C9—C10A	−10.2 (12)	C20—C21—C22—C17	0.6 (7)
C7—C8—C9—C10A	170.3 (12)	C18—C17—C22—C21	−1.5 (6)
C13—C8—C9—C10B	18.1 (7)	C16—C17—C22—C21	179.2 (4)
C7—C8—C9—C10B	−161.4 (7)	C8—C9—C10A—C11	21 (2)
C14—C11—C12—O1	−5.8 (4)	C10B—C9—C10A—C11	−71 (2)
C10B—C11—C12—O1	163.7 (6)	C14—C11—C10A—C9	175.7 (12)
C10A—C11—C12—O1	−168.3 (10)	C12—C11—C10A—C9	−22 (2)
C14—C11—C12—C13	174.2 (3)	C10B—C11—C10A—C9	73.4 (19)
C10B—C11—C12—C13	−16.3 (7)	C10A—C9—C10B—C11	65.1 (18)
C10A—C11—C12—C13	11.7 (11)	C8—C9—C10B—C11	−34.9 (12)
C2—N1—C13—C8	−0.8 (3)	C14—C11—C10B—C9	−155.8 (6)
C2—N1—C13—C12	−179.8 (3)	C12—C11—C10B—C9	35.4 (12)
C7—C8—C13—N1	1.0 (3)	C10A—C11—C10B—C9	−62 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.82 (3)	2.02 (3)	2.813 (3)	161 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.82 (3)	2.02 (3)	2.813 (3)	161 (3)

Symmetry code: (i) .