Literature DB >> 21754808

9-(4-Nitro-phenyl-sulfon-yl)-9H-carbazole.

Nesimi Uludağ, Murat Ateş, Barış Tercan, Tuncer Hökelek.

Abstract

In the title mol-ecule, C(18)H(12)N(2)O(4)S, the carbazole skeleton is nearly planar [maximum deviation = 0.037 (1) Å] and is oriented at a dihedral angle of 73.73 (5)° with respect to the benzene ring. An intra-molecular C-H⋯O hydrogen bond links a nitro O atom to the carbazole skeleton. In the crystal, inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into a three-dimensional network. π-π contacts between inversion-related benzene rings [centroid-centroid distance = 3.7828 (8) Å] and two weak C-H⋯π inter-actions may also stabilize the structure.

Entities: Chemical Disease Species

Year: 2011 PMID： 21754808 PMCID： PMC3120556 DOI： 10.1107/S1600536811017818

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

Related literature

For tetrahydrocarbazole systems present in the framework of a number of indole-type alkaloids of biological interest, see: Saxton (1983 ▶). For related structures, see: Hökelek et al. (1994 ▶, 1998, ▶ 1999) ▶; Patır et al. (1997 ▶); Hökelek & Patır (1999 ▶). For the role of carbazole-based compounds in electroactive materials, see: Morin et al. (2004 ▶); Pasquali et al. (1993 ▶). For applications of chemically or electrochemically polymerized carbazole-based heterocyclic polymer systems, see: Sacak (1999 ▶); Santhanam & Sundaresan (1986 ▶).

Experimental

Crystal data

C18H12N2O4S M = 352.37 Monoclinic, a = 7.4877 (2) Å b = 11.7612 (3) Å c = 17.3744 (4) Å β = 90.119 (2)° V = 1530.06 (7) Å3 Z = 4 Mo Kα radiation μ = 0.24 mm−1 T = 100 K 0.35 × 0.30 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.921, T max = 0.943 26862 measured reflections 3824 independent reflections 3269 reflections with I > 2σ(I) R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.034 wR(F 2) = 0.091 S = 1.06 3824 reflections 226 parameters H-atom parameters constrained Δρmax = 0.43 e Å−3 Δρmin = −0.54 e Å−3 Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶). Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811017818/su2273sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536811017818/su2273Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536811017818/su2273Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₈H₁₂N₂O₄S	F(000) = 728
M_r = 352.37	D_x = 1.530 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8540 reflections
a = 7.4877 (2) Å	θ = 2.3–28.2°
b = 11.7612 (3) Å	µ = 0.24 mm⁻¹
c = 17.3744 (4) Å	T = 100 K
β = 90.119 (2)°	Block, yellow
V = 1530.06 (7) Å³	0.35 × 0.30 × 0.25 mm
Z = 4

Bruker Kappa APEXII CCD area-detector diffractometer	3824 independent reflections
Radiation source: fine-focus sealed tube	3269 reflections with I > 2σ(I)
graphite	R_int = 0.033
φ and ω scans	θ_max = 28.4°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −9→10
T_min = 0.921, T_max = 0.943	k = −15→15
26862 measured reflections	l = −23→23

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.091	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0412P)² + 0.8621P] where P = (F_o² + 2F_c²)/3
3824 reflections	(Δ/σ)_max = 0.001
226 parameters	Δρ_max = 0.43 e Å⁻³
0 restraints	Δρ_min = −0.54 e Å⁻³

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
S1	0.34852 (5)	0.62068 (3)	0.145676 (18)	0.01632 (10)
O1	0.42494 (14)	0.73081 (8)	0.13727 (6)	0.0213 (2)
O2	0.17638 (14)	0.59697 (9)	0.11410 (6)	0.0206 (2)
O3	1.02664 (14)	0.30584 (10)	0.02810 (6)	0.0245 (2)
O4	0.82092 (16)	0.17612 (9)	0.03061 (7)	0.0293 (3)
C1	0.6420 (2)	0.67140 (12)	0.27841 (8)	0.0196 (3)
H1	0.6511	0.7244	0.2373	0.023*
C2	0.7764 (2)	0.66037 (13)	0.33332 (8)	0.0212 (3)
H2	0.8799	0.7067	0.3293	0.025*
C3	0.7637 (2)	0.58338 (13)	0.39410 (8)	0.0219 (3)
H3	0.8579	0.5780	0.4306	0.026*
C4	0.6144 (2)	0.51468 (12)	0.40160 (8)	0.0200 (3)
H4	0.6050	0.4625	0.4431	0.024*
C4A	0.47842 (19)	0.52351 (11)	0.34712 (8)	0.0169 (3)
C5	0.2241 (2)	0.38241 (12)	0.38254 (8)	0.0207 (3)
H5	0.2768	0.3555	0.4289	0.025*
C5A	0.30977 (19)	0.46441 (11)	0.33801 (8)	0.0170 (3)
C6	0.0606 (2)	0.34090 (13)	0.35799 (9)	0.0236 (3)
H6	0.0017	0.2839	0.3872	0.028*
C7	−0.0187 (2)	0.38190 (13)	0.29076 (9)	0.0242 (3)
H7	−0.1305	0.3517	0.2749	0.029*
C8	0.0618 (2)	0.46567 (13)	0.24653 (8)	0.0217 (3)
H8	0.0060	0.4947	0.2015	0.026*
C8A	0.22741 (19)	0.50524 (12)	0.27093 (8)	0.0171 (3)
C9A	0.49421 (19)	0.60138 (12)	0.28645 (7)	0.0167 (3)
N9	0.33693 (16)	0.59368 (10)	0.23925 (6)	0.0172 (2)
N10	0.87222 (17)	0.27414 (11)	0.03883 (7)	0.0203 (3)
C10	0.50149 (19)	0.51933 (11)	0.11037 (7)	0.0161 (3)
C11	0.44419 (19)	0.40771 (12)	0.09937 (8)	0.0182 (3)
H11	0.3229	0.3877	0.1079	0.022*
C12	0.56592 (19)	0.32637 (12)	0.07590 (8)	0.0188 (3)
H12	0.5308	0.2495	0.0685	0.023*
C13	0.74049 (19)	0.36034 (12)	0.06344 (7)	0.0171 (3)
C14	0.79846 (19)	0.47121 (12)	0.07233 (8)	0.0185 (3)
H14	0.9189	0.4914	0.0619	0.022*
C15	0.67725 (19)	0.55191 (12)	0.09676 (8)	0.0186 (3)
H15	0.7133	0.6286	0.1042	0.022*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.01736 (18)	0.01617 (17)	0.01543 (16)	0.00119 (12)	−0.00067 (12)	0.00134 (11)
O1	0.0250 (6)	0.0167 (5)	0.0222 (5)	0.0004 (4)	−0.0002 (4)	0.0026 (4)
O2	0.0177 (5)	0.0243 (5)	0.0199 (5)	0.0023 (4)	−0.0027 (4)	0.0017 (4)
O3	0.0162 (5)	0.0306 (6)	0.0267 (5)	0.0036 (4)	−0.0001 (4)	0.0016 (4)
O4	0.0294 (6)	0.0202 (6)	0.0384 (6)	0.0028 (5)	0.0022 (5)	−0.0033 (5)
C1	0.0222 (7)	0.0186 (7)	0.0180 (6)	−0.0013 (6)	0.0006 (5)	−0.0012 (5)
C2	0.0192 (7)	0.0214 (7)	0.0229 (7)	−0.0032 (6)	0.0002 (5)	−0.0050 (5)
C3	0.0215 (8)	0.0226 (7)	0.0216 (7)	0.0028 (6)	−0.0041 (5)	−0.0038 (5)
C4	0.0245 (8)	0.0178 (6)	0.0177 (6)	0.0033 (6)	−0.0018 (5)	−0.0007 (5)
C4A	0.0189 (7)	0.0146 (6)	0.0172 (6)	0.0015 (5)	0.0011 (5)	−0.0022 (5)
C5	0.0264 (8)	0.0171 (6)	0.0186 (6)	0.0022 (6)	0.0039 (5)	−0.0001 (5)
C5A	0.0194 (7)	0.0151 (6)	0.0166 (6)	0.0024 (5)	0.0017 (5)	−0.0031 (5)
C6	0.0256 (8)	0.0202 (7)	0.0250 (7)	−0.0036 (6)	0.0078 (6)	−0.0008 (6)
C7	0.0193 (8)	0.0275 (8)	0.0260 (7)	−0.0043 (6)	0.0036 (6)	−0.0034 (6)
C8	0.0191 (7)	0.0258 (7)	0.0201 (6)	−0.0008 (6)	0.0001 (5)	−0.0012 (5)
C8A	0.0182 (7)	0.0161 (6)	0.0171 (6)	0.0008 (5)	0.0032 (5)	−0.0010 (5)
C9A	0.0174 (7)	0.0174 (6)	0.0153 (6)	0.0021 (5)	−0.0014 (5)	−0.0031 (5)
N9	0.0175 (6)	0.0191 (6)	0.0149 (5)	−0.0014 (5)	−0.0011 (4)	0.0007 (4)
C10	0.0179 (7)	0.0174 (6)	0.0131 (6)	0.0013 (5)	−0.0012 (5)	0.0012 (5)
N10	0.0212 (7)	0.0222 (6)	0.0176 (5)	0.0034 (5)	−0.0014 (4)	0.0012 (4)
C11	0.0155 (7)	0.0195 (7)	0.0196 (6)	−0.0018 (5)	−0.0003 (5)	0.0026 (5)
C12	0.0209 (7)	0.0166 (6)	0.0189 (6)	−0.0020 (5)	−0.0010 (5)	0.0013 (5)
C13	0.0178 (7)	0.0197 (7)	0.0139 (6)	0.0032 (5)	−0.0008 (5)	0.0008 (5)
C14	0.0151 (7)	0.0238 (7)	0.0165 (6)	−0.0028 (5)	−0.0009 (5)	−0.0001 (5)
C15	0.0202 (7)	0.0181 (6)	0.0175 (6)	−0.0030 (5)	−0.0010 (5)	0.0010 (5)

S1—O1	1.4237 (11)	C7—C8	1.388 (2)
S1—O2	1.4272 (11)	C7—H7	0.9500
S1—N9	1.6589 (11)	C8—H8	0.9500
S1—C10	1.7641 (14)	C8A—C8	1.390 (2)
O3—N10	1.2295 (17)	C8A—C5A	1.4023 (19)
O4—N10	1.2233 (17)	C9A—C1	1.387 (2)
C1—C2	1.391 (2)	C9A—C4A	1.4016 (19)
C1—H1	0.9500	N9—C8A	1.4349 (18)
C2—H2	0.9500	N9—C9A	1.4366 (17)
C3—C2	1.395 (2)	C10—C11	1.3941 (19)
C3—H3	0.9500	N10—C13	1.4783 (18)
C4—C3	1.385 (2)	C11—C12	1.383 (2)
C4—H4	0.9500	C11—H11	0.9500
C4A—C4	1.3929 (19)	C12—H12	0.9500
C4A—C5A	1.450 (2)	C13—C12	1.384 (2)
C5—C6	1.384 (2)	C13—C14	1.383 (2)
C5—H5	0.9500	C14—C15	1.381 (2)
C5A—C5	1.3938 (19)	C14—H14	0.9500
C6—C7	1.395 (2)	C15—C10	1.391 (2)
C6—H6	0.9500	C15—H15	0.9500

O1—S1—O2	120.07 (6)	C5A—C5—H5	120.6
O1—S1—N9	107.25 (6)	C6—C5—C5A	118.74 (13)
O1—S1—C10	108.53 (7)	C6—C5—H5	120.6
O2—S1—N9	106.87 (6)	C5—C5A—C4A	132.31 (13)
O2—S1—C10	108.71 (6)	C5—C5A—C8A	119.75 (13)
N9—S1—C10	104.29 (6)	C8A—C5A—C4A	107.94 (12)
C1—C9A—N9	129.31 (13)	C5—C6—C7	120.69 (14)
C1—C9A—C4A	122.17 (13)	C5—C6—H6	119.7
C4A—C9A—N9	108.53 (12)	C7—C6—H6	119.7
C8A—N9—S1	123.08 (9)	C8—C7—C6	121.65 (14)
C8A—N9—C9A	107.17 (11)	C8—C7—H7	119.2
C9A—N9—S1	120.19 (10)	C6—C7—H7	119.2
C11—C10—S1	118.95 (11)	C7—C8—C8A	117.18 (13)
C15—C10—S1	119.21 (11)	C7—C8—H8	121.4
C15—C10—C11	121.80 (13)	C8A—C8—H8	121.4
O3—N10—C13	117.65 (12)	C5A—C8A—N9	108.44 (12)
O4—N10—O3	124.28 (13)	C8—C8A—N9	129.49 (13)
O4—N10—C13	118.07 (12)	C8—C8A—C5A	121.96 (13)
C2—C1—H1	121.6	C10—C11—H11	120.4
C9A—C1—C2	116.86 (13)	C12—C11—C10	119.26 (13)
C9A—C1—H1	121.6	C12—C11—H11	120.4
C1—C2—C3	121.96 (14)	C11—C12—C13	118.00 (13)
C1—C2—H2	119.0	C11—C12—H12	121.0
C3—C2—H2	119.0	C13—C12—H12	121.0
C2—C3—H3	119.8	C12—C13—N10	118.56 (12)
C4—C3—C2	120.42 (13)	C14—C13—N10	118.00 (13)
C4—C3—H3	119.8	C14—C13—C12	123.44 (13)
C3—C4—C4A	118.77 (13)	C13—C14—H14	120.8
C3—C4—H4	120.6	C15—C14—C13	118.43 (13)
C4A—C4—H4	120.6	C15—C14—H14	120.8
C4—C4A—C5A	132.37 (13)	C10—C15—H15	120.5
C4—C4A—C9A	119.81 (13)	C14—C15—C10	119.05 (13)
C9A—C4A—C5A	107.82 (12)	C14—C15—H15	120.5

O1—S1—N9—C8A	163.45 (11)	N9—C8A—C8—C7	−176.89 (14)
O1—S1—N9—C9A	−54.69 (12)	C5A—C8A—C8—C7	−1.1 (2)
O2—S1—N9—C8A	33.47 (12)	S1—N9—C8A—C5A	149.32 (10)
O2—S1—N9—C9A	175.33 (10)	S1—N9—C8A—C8	−34.4 (2)
C10—S1—N9—C8A	−81.56 (12)	C9A—N9—C8A—C5A	3.29 (14)
C10—S1—N9—C9A	60.30 (11)	C9A—N9—C8A—C8	179.53 (14)
O1—S1—C10—C11	−168.31 (10)	S1—N9—C9A—C1	30.83 (19)
O1—S1—C10—C15	13.85 (12)	S1—N9—C9A—C4A	−149.61 (10)
O2—S1—C10—C11	−36.13 (12)	C8A—N9—C9A—C1	178.04 (14)
O2—S1—C10—C15	146.03 (11)	C8A—N9—C9A—C4A	−2.41 (14)
N9—S1—C10—C11	77.60 (11)	N9—C9A—C1—C2	−179.94 (13)
N9—S1—C10—C15	−100.24 (11)	C4A—C9A—C1—C2	0.6 (2)
C9A—C1—C2—C3	−0.5 (2)	C1—C9A—C4A—C4	−0.2 (2)
C4—C3—C2—C1	0.0 (2)	C1—C9A—C4A—C5A	−179.76 (12)
C4A—C4—C3—C2	0.4 (2)	N9—C9A—C4A—C4	−179.76 (12)
C5A—C4A—C4—C3	179.14 (14)	N9—C9A—C4A—C5A	0.65 (15)
C9A—C4A—C4—C3	−0.3 (2)	O3—N10—C13—C12	−179.94 (12)
C4—C4A—C5A—C5	3.1 (3)	O3—N10—C13—C14	0.47 (18)
C4—C4A—C5A—C8A	−178.12 (14)	O4—N10—C13—C12	−0.09 (18)
C9A—C4A—C5A—C5	−177.34 (14)	O4—N10—C13—C14	−179.68 (12)
C9A—C4A—C5A—C8A	1.40 (15)	S1—C10—C11—C12	−176.34 (10)
C5A—C5—C6—C7	−1.2 (2)	C15—C10—C11—C12	1.4 (2)
C4A—C5A—C5—C6	−179.66 (14)	C10—C11—C12—C13	−0.7 (2)
C8A—C5A—C5—C6	1.7 (2)	N10—C13—C12—C11	179.61 (12)
C5—C6—C7—C8	−0.5 (2)	C14—C13—C12—C11	−0.8 (2)
C6—C7—C8—C8A	1.6 (2)	N10—C13—C14—C15	−178.75 (12)
N9—C8A—C5A—C4A	−2.90 (15)	C12—C13—C14—C15	1.7 (2)
N9—C8A—C5A—C5	176.02 (12)	C13—C14—C15—C10	−0.94 (19)
C8—C8A—C5A—C4A	−179.48 (13)	C14—C15—C10—S1	177.20 (10)
C8—C8A—C5A—C5	−0.6 (2)	C14—C15—C10—C11	−0.6 (2)

Cg2 and Cg3 are the centroids of the C1–C4/C4A/C9A and C5A/C5–C8/C8A rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O1	0.95	2.43	3.0210 (18)	121
C6—H6···O2ⁱ	0.95	2.57	3.4085 (19)	147
C14—H14···O2ⁱⁱ	0.95	2.46	3.2731 (18)	143
C1—H1···Cg3ⁱⁱⁱ	0.95	2.94	3.7368 (15)	142
C12—H12···Cg2^iv	0.95	2.71	3.4376 (15)	134

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are the centroids of the C1–C4/C4A/C9A and C5A/C5–C8/C8A rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O1	0.95	2.43	3.0210 (18)	121
C6—H6⋯O2ⁱ	0.95	2.57	3.4085 (19)	147
C14—H14⋯O2ⁱⁱ	0.95	2.46	3.2731 (18)	143
C1—H1⋯Cg3ⁱⁱⁱ	0.95	2.94	3.7368 (15)	142
C12—H12⋯Cg2^iv	0.95	2.71	3.4376 (15)	134

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .

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. Structure validation in chemical crystallography.

Authors: Anthony L Spek
Journal: Acta Crystallogr D Biol Crystallogr Date: 2009-01-20

2 in total

1 in total

1. 2,3,6,7-Tetra-bromo-9-butyl-9H-carbazole.

Authors: J Josephine Novina; G Vasuki; Sushil Kumar; K R Justin Thomas
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2012-04-13

1 in total