Literature DB >> 21203324

6-Chloro-3,4-di-hydro-9H-carbazol-1(2H)-one.

M Sridharan, K J Rajendra Prasad, A Thomas Gunaseelan, A Thiruvalluvar, R J Butcher.

Abstract

The carbazole unit of the title mol-ecule, C(12)H(10)ClNO, is not planar. The dihedral angle between the benzene and pyrrole rings is 1.35 (10)°. The cyclo-hexene ring adopts an envelope conformation. In the crystal structure, inter-molecular N-H⋯O hydrogen bonds form centrosymmetric dimers.

Entities: Chemical Disease Gene

Year: 2008 PMID： 21203324 PMCID： PMC2962081 DOI： 10.1107/S1600536808023441

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For a related structure with a non-planar carbazole unit, see: Sridharan et al. (2008 ▶).

Experimental

Crystal data

C12H10ClNO M = 219.66 Monoclinic, a = 10.4211 (5) Å b = 5.6851 (3) Å c = 17.0824 (10) Å β = 100.239 (6)° V = 995.93 (9) Å3 Z = 4 Mo Kα radiation μ = 0.35 mm−1 T = 200 (2) K 0.58 × 0.18 × 0.11 mm

Data collection

Oxford Diffraction R Gemini diffractometer Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 ▶) T min = 0.923, T max = 1.000 (expected range = 0.888–0.962) 10695 measured reflections 3909 independent reflections 1793 reflections with I > 2σ(I) R int = 0.072

Refinement

R[F 2 > 2σ(F 2)] = 0.062 wR(F 2) = 0.139 S = 0.88 3909 reflections 140 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.46 e Å−3 Δρmin = −0.23 e Å−3 Data collection: CrysAlis CCD (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 ▶); data reduction: CrysAlis RED; 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: PLATON (Spek, 2003 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808023441/sj2518sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536808023441/sj2518Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₂H₁₀ClNO	F₀₀₀ = 456
M_r = 219.66	D_x = 1.465 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 475(1) K
Hall symbol: -P 2ybc	Mo Kα radiation λ = 0.71073 Å
a = 10.4211 (5) Å	Cell parameters from 1948 reflections
b = 5.6851 (3) Å	θ = 4.6–34.7º
c = 17.0824 (10) Å	µ = 0.35 mm⁻¹
β = 100.239 (6)º	T = 200 (2) K
V = 995.93 (9) Å³	Needle, colourless
Z = 4	0.58 × 0.18 × 0.11 mm

Oxford Diffraction R Gemini diffractometer	3909 independent reflections
Radiation source: fine-focus sealed tube	1793 reflections with I > 2σ(I)
Monochromator: graphite	R_int = 0.072
Detector resolution: 10.5081 pixels mm^-1	θ_max = 34.7º
T = 200(2) K	θ_min = 4.6º
φ and ω scans	h = −16→15
Absorption correction: multi-scan(CrysAlis RED; Oxford Diffraction, 2008)	k = −9→9
T_min = 0.923, T_max = 1.000	l = −27→19
10695 measured reflections

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.062	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.139	w = 1/[σ²(F_o²) + (0.0611P)²] where P = (F_o² + 2F_c²)/3
S = 0.88	(Δ/σ)_max = 0.001
3909 reflections	Δρ_max = 0.46 e Å⁻³
140 parameters	Δρ_min = −0.23 e Å⁻³
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	U_iso*/U_eq
Cl1	0.51516 (5)	0.81197 (10)	−0.14449 (3)	0.0418 (2)
O1	−0.02083 (14)	0.1402 (3)	0.10672 (9)	0.0403 (5)
N9	0.14769 (15)	0.2338 (3)	−0.00949 (10)	0.0293 (5)
C1	0.05496 (17)	0.3080 (3)	0.11410 (11)	0.0276 (5)
C2	0.06417 (19)	0.4778 (4)	0.18253 (12)	0.0340 (6)
C3	0.1973 (2)	0.5983 (4)	0.20336 (12)	0.0361 (6)
C4	0.2388 (2)	0.7173 (4)	0.13273 (12)	0.0358 (7)
C4A	0.22083 (17)	0.5536 (3)	0.06315 (11)	0.0258 (5)
C4B	0.28050 (17)	0.5475 (3)	−0.00559 (11)	0.0251 (5)
C5	0.36953 (17)	0.6955 (3)	−0.03472 (12)	0.0286 (5)
C6	0.40706 (18)	0.6321 (3)	−0.10471 (12)	0.0292 (6)
C7	0.36271 (19)	0.4274 (4)	−0.14660 (12)	0.0337 (6)
C8	0.27603 (19)	0.2811 (4)	−0.11885 (12)	0.0318 (6)
C8A	0.23419 (17)	0.3435 (3)	−0.04868 (11)	0.0260 (5)
C9A	0.13871 (17)	0.3614 (3)	0.05784 (11)	0.0253 (5)
H2A	−0.00399	0.59971	0.16903	0.0408*
H2B	0.04640	0.39204	0.22991	0.0408*
H3A	0.26364	0.47952	0.22511	0.0433*
H3B	0.19391	0.71695	0.24535	0.0433*
H4A	0.33155	0.76429	0.14653	0.0430*
H4B	0.18603	0.86099	0.11876	0.0430*
H5	0.40231	0.83389	−0.00698	0.0343*
H7	0.39275	0.38971	−0.19443	0.0404*
H8	0.24555	0.14153	−0.14666	0.0381*
H9	0.1137 (19)	0.107 (4)	−0.0230 (12)	0.023 (5)*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0407 (3)	0.0437 (3)	0.0464 (3)	−0.0017 (2)	0.0224 (2)	0.0095 (3)
O1	0.0350 (7)	0.0496 (9)	0.0389 (8)	−0.0151 (7)	0.0138 (7)	−0.0069 (8)
N9	0.0308 (8)	0.0319 (9)	0.0269 (8)	−0.0096 (7)	0.0095 (7)	−0.0062 (8)
C1	0.0222 (8)	0.0333 (10)	0.0273 (9)	0.0006 (8)	0.0046 (7)	0.0012 (9)
C2	0.0336 (10)	0.0437 (12)	0.0271 (10)	−0.0017 (9)	0.0119 (9)	−0.0023 (10)
C3	0.0424 (11)	0.0397 (12)	0.0279 (10)	−0.0077 (9)	0.0109 (9)	−0.0051 (10)
C4	0.0459 (12)	0.0306 (11)	0.0333 (11)	−0.0057 (9)	0.0138 (10)	−0.0061 (10)
C4A	0.0265 (9)	0.0262 (9)	0.0250 (9)	0.0022 (7)	0.0051 (8)	0.0012 (9)
C4B	0.0255 (8)	0.0275 (10)	0.0223 (9)	0.0020 (7)	0.0043 (7)	0.0035 (8)
C5	0.0302 (9)	0.0269 (10)	0.0294 (9)	−0.0009 (8)	0.0071 (8)	0.0023 (9)
C6	0.0273 (9)	0.0319 (11)	0.0305 (10)	0.0040 (7)	0.0113 (8)	0.0085 (9)
C7	0.0355 (10)	0.0412 (12)	0.0266 (9)	0.0051 (9)	0.0117 (9)	0.0005 (10)
C8	0.0344 (10)	0.0348 (11)	0.0276 (10)	−0.0007 (8)	0.0097 (8)	−0.0046 (9)
C8A	0.0244 (8)	0.0302 (10)	0.0240 (9)	0.0004 (7)	0.0057 (7)	0.0006 (9)
C9A	0.0240 (8)	0.0287 (10)	0.0238 (9)	0.0026 (7)	0.0056 (7)	0.0007 (8)

Cl1—C6	1.7460 (19)	C5—C6	1.371 (3)
O1—C1	1.231 (2)	C6—C7	1.401 (3)
N9—C8A	1.365 (2)	C7—C8	1.373 (3)
N9—C9A	1.377 (2)	C8—C8A	1.392 (3)
N9—H9	0.82 (2)	C2—H2A	0.9900
C1—C9A	1.441 (3)	C2—H2B	0.9900
C1—C2	1.506 (3)	C3—H3A	0.9900
C2—C3	1.531 (3)	C3—H3B	0.9900
C3—C4	1.512 (3)	C4—H4A	0.9900
C4—C4A	1.495 (3)	C4—H4B	0.9900
C4A—C4B	1.424 (3)	C5—H5	0.9500
C4A—C9A	1.381 (2)	C7—H7	0.9500
C4B—C8A	1.412 (2)	C8—H8	0.9500
C4B—C5	1.407 (3)

Cl1···C4Aⁱ	3.5299 (19)	C8A···H2A^vi	2.8900
Cl1···H7ⁱⁱ	3.1000	C9A···H3A	3.0000
Cl1···H4Aⁱⁱⁱ	2.8900	C9A···H4B^v	3.0400
O1···N9	2.924 (2)	H2A···H2B^x	2.4900
O1···N9^iv	2.872 (2)	H2A···C8^vi	2.8900
O1···H4B^v	2.6600	H2A···C8A^vi	2.8900
O1···H9	2.83 (2)	H2B···H2A^xi	2.4900
O1···H9^iv	2.11 (2)	H3A···C9A	3.0000
N9···O1	2.924 (2)	H3A···C8^vii	3.0300
N9···O1^iv	2.872 (2)	H3A···H8^vii	2.3400
C4A···Cl1ⁱ	3.5299 (19)	H3B···C7^xii	3.0700
C5···C5ⁱ	3.549 (3)	H4A···Cl1ⁱⁱⁱ	2.8900
C5···C6ⁱ	3.548 (3)	H4B···O1^xiii	2.6600
C6···C5ⁱ	3.548 (3)	H4B···C1^xiii	2.8800
C9A···C9A^vi	3.566 (3)	H4B···C9A^xiii	3.0400
C1···H4B^v	2.8800	H7···Cl1^xiv	3.1000
C3···H8^vii	2.8700	H8···C3^ix	2.8700
C7···H3B^viii	3.0700	H8···H3A^ix	2.3400
C8···H2A^vi	2.8900	H9···O1	2.83 (2)
C8···H3A^ix	3.0300	H9···O1^iv	2.11 (2)

C8A—N9—C9A	108.53 (15)	C1—C9A—C4A	124.38 (17)
C9A—N9—H9	127.6 (14)	N9—C9A—C1	125.83 (16)
C8A—N9—H9	123.7 (14)	N9—C9A—C4A	109.78 (16)
O1—C1—C9A	123.29 (17)	C1—C2—H2A	109.00
O1—C1—C2	121.85 (17)	C1—C2—H2B	109.00
C2—C1—C9A	114.85 (16)	C3—C2—H2A	109.00
C1—C2—C3	113.41 (16)	C3—C2—H2B	109.00
C2—C3—C4	112.99 (17)	H2A—C2—H2B	108.00
C3—C4—C4A	110.04 (18)	C2—C3—H3A	109.00
C4B—C4A—C9A	106.44 (16)	C2—C3—H3B	109.00
C4—C4A—C4B	131.28 (17)	C4—C3—H3A	109.00
C4—C4A—C9A	122.24 (17)	C4—C3—H3B	109.00
C5—C4B—C8A	119.51 (17)	H3A—C3—H3B	108.00
C4A—C4B—C8A	106.93 (15)	C3—C4—H4A	110.00
C4A—C4B—C5	133.57 (17)	C3—C4—H4B	110.00
C4B—C5—C6	117.36 (16)	C4A—C4—H4A	110.00
Cl1—C6—C5	119.30 (14)	C4A—C4—H4B	110.00
Cl1—C6—C7	117.70 (15)	H4A—C4—H4B	108.00
C5—C6—C7	123.00 (17)	C4B—C5—H5	121.00
C6—C7—C8	120.30 (19)	C6—C5—H5	121.00
C7—C8—C8A	117.96 (19)	C6—C7—H7	120.00
N9—C8A—C8	129.85 (17)	C8—C7—H7	120.00
C4B—C8A—C8	121.86 (17)	C7—C8—H8	121.00
N9—C8A—C4B	108.29 (16)	C8A—C8—H8	121.00

C9A—N9—C8A—C4B	−0.6 (2)	C4—C4A—C4B—C8A	175.46 (19)
C9A—N9—C8A—C8	179.52 (19)	C9A—C4A—C4B—C5	178.3 (2)
C8A—N9—C9A—C1	178.12 (17)	C4B—C4A—C9A—N9	1.7 (2)
C8A—N9—C9A—C4A	−0.7 (2)	C4B—C4A—C9A—C1	−177.15 (17)
C2—C1—C9A—N9	−179.78 (17)	C4A—C4B—C8A—N9	1.6 (2)
C2—C1—C9A—C4A	−1.1 (3)	C5—C4B—C8A—C8	1.3 (3)
O1—C1—C2—C3	153.79 (19)	C4A—C4B—C8A—C8	−178.47 (18)
C9A—C1—C2—C3	−27.7 (2)	C5—C4B—C8A—N9	−178.63 (16)
O1—C1—C9A—N9	−1.3 (3)	C4A—C4B—C5—C6	179.7 (2)
O1—C1—C9A—C4A	177.38 (18)	C8A—C4B—C5—C6	0.0 (3)
C1—C2—C3—C4	53.7 (2)	C4B—C5—C6—Cl1	178.90 (14)
C2—C3—C4—C4A	−48.1 (2)	C4B—C5—C6—C7	−1.2 (3)
C3—C4—C4A—C4B	−157.05 (19)	Cl1—C6—C7—C8	−178.99 (16)
C3—C4—C4A—C9A	20.1 (3)	C5—C6—C7—C8	1.1 (3)
C4—C4A—C9A—N9	−176.05 (17)	C6—C7—C8—C8A	0.2 (3)
C4—C4A—C9A—C1	5.1 (3)	C7—C8—C8A—N9	178.52 (19)
C9A—C4A—C4B—C8A	−2.0 (2)	C7—C8—C8A—C4B	−1.4 (3)
C4—C4A—C4B—C5	−4.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N9—H9···O1^iv	0.82 (2)	2.11 (2)	2.872 (2)	154 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N9—H9⋯O1ⁱ	0.82 (2)	2.11 (2)	2.872 (2)	154 (2)

Symmetry code: (i) .

2 in total

1. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

2. 6-Meth-oxy-2,3,4,9-tetra-hydro-1H-carbazol-1-one.

Authors: M Sridharan; K J Rajendra Prasad; A Thomas Gunaseelan; A Thiruvalluvar; A Linden
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2008-03-29

2 in total