Crystal structure of ethyl 2-phenyl-9-phenyl-sulfonyl-9H-carbazole-3-carboxyl-ate.

In the title compound, C27H21NO4S, the dihedral angles between the carbazole ring system (r.m.s. deviation = 0.015 Å) and the sulfur-bonded and directly linked benzene rings are 79.98 (11) and 53.51 (18)°, respectively. The benzene rings subtend a dihedral angle of 48.4 (2)°. The ethyl side chain of the ester group has an extended conformation [C-O-C-C = -172.3 (3)°]. In the crystal, inversion dimers linked by pairs of weak C-H⋯O hydrogen bonds generate R 2 (2)(22) loops. The dimers are linked by weak C-H⋯π and π-π [centroid-to-centroid distances ranging from 3.5042 (14) to 3.888 (2) Å] inter-actions, thereby forming a three-dimensional supra-molecular network.

Related literature

For the biological activity of indole derivatives, see: Itoigawa et al. (2000 ▸); Ramsewak et al. (1999 ▸). For related structures, see: Chakkaravarthi et al. (2008 ▸, 2009 ▸).

Experimental

Crystal data

C27H21NO4S

M = 455.51

Monoclinic,

a = 13.7655 (8) Å

b = 7.8207 (4) Å

c = 20.9500 (12) Å

β = 94.054 (2)°

V = 2249.7 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.18 mm−1

T = 295 K

0.28 × 0.26 × 0.24 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▸) T min = 0.952, T max = 0.958

39017 measured reflections

4997 independent reflections

2939 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.146

S = 1.04

4997 reflections

299 parameters

4 restraints

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.34 e Å−3

Data collection: APEX2 (Bruker, 2004 ▸); cell refinement: SAINT (Bruker, 2004 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▸); molecular graphics: PLATON (Spek, 2009 ▸); software used to prepare material for publication: SHELXL97 and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S205698901501662X/hb7499sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S205698901501662X/hb7499Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S205698901501662X/hb7499Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S205698901501662X/hb7499fig1.tif

The mol­ecular structure of (I), with 30% probability displacement ellipsoids for non-H atoms.

Click here for additional data file.

b . DOI: 10.1107/S205698901501662X/hb7499fig2.tif

The crystal packing of the title compound viewed along the b axis. The hydrogen bonds are shown as dashed lines (see Table 1), and C-bound H atoms have been omitted for clarity.

CCDC reference: 1422541

Additional supporting information: crystallographic information; 3D view; checkCIF report

C27H21NO4S	F(000) = 952
Mr = 455.51	Dx = 1.345 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9043 reflections
a = 13.7655 (8) Å	θ = 2.8–24.7°
b = 7.8207 (4) Å	µ = 0.18 mm−1
c = 20.9500 (12) Å	T = 295 K
β = 94.054 (2)°	Block, colourless
V = 2249.7 (2) Å3	0.28 × 0.26 × 0.24 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	4997 independent reflections
Radiation source: fine-focus sealed tube	2939 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.048
ω and φ scan	θmax = 27.3°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −17→17
Tmin = 0.952, Tmax = 0.958	k = −9→9
39017 measured reflections	l = −26→26

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0543P)2 + 1.1538P] where P = (Fo2 + 2Fc2)/3
4997 reflections	(Δ/σ)max < 0.001
299 parameters	Δρmax = 0.19 e Å−3
4 restraints	Δρmin = −0.34 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
C1	0.66860 (19)	0.3090 (3)	0.66383 (11)	0.0483 (6)
C2	0.6003 (2)	0.4052 (4)	0.69291 (13)	0.0620 (7)
H2	0.5399	0.3594	0.7007	0.074*
C3	0.6240 (3)	0.5717 (4)	0.71020 (15)	0.0806 (10)
H3	0.5791	0.6392	0.7298	0.097*
C4	0.7125 (3)	0.6369 (4)	0.69873 (15)	0.0834 (11)
H4	0.7273	0.7492	0.7103	0.100*
C5	0.7798 (3)	0.5405 (5)	0.67054 (16)	0.0807 (10)
H5	0.8403	0.5869	0.6634	0.097*
C6	0.7586 (2)	0.3740 (4)	0.65255 (13)	0.0625 (7)
H6	0.8041	0.3074	0.6332	0.075*
C7	0.48068 (17)	0.1830 (3)	0.55839 (12)	0.0469 (6)
C8	0.4049 (2)	0.1610 (3)	0.59744 (14)	0.0597 (7)
H8	0.4138	0.1059	0.6367	0.072*
C9	0.3155 (2)	0.2248 (4)	0.57535 (17)	0.0699 (9)
H9	0.2632	0.2133	0.6007	0.084*
C10	0.3011 (2)	0.3051 (4)	0.51685 (17)	0.0708 (9)
H10	0.2395	0.3462	0.5036	0.085*
C11	0.37638 (19)	0.3250 (4)	0.47802 (15)	0.0600 (7)
H11	0.3667	0.3787	0.4385	0.072*
C12	0.46766 (17)	0.2630 (3)	0.49929 (12)	0.0470 (6)
C13	0.55983 (17)	0.2628 (3)	0.47067 (11)	0.0426 (6)
C14	0.58915 (19)	0.3254 (3)	0.41368 (12)	0.0497 (6)
H14	0.5440	0.3765	0.3846	0.060*
C15	0.68539 (19)	0.3126 (3)	0.39965 (11)	0.0475 (6)
C16	0.75333 (18)	0.2285 (3)	0.44225 (12)	0.0466 (6)
C17	0.72340 (17)	0.1631 (3)	0.49910 (11)	0.0444 (6)
H17	0.7673	0.1061	0.5274	0.053*
C18	0.62778 (17)	0.1835 (3)	0.51332 (11)	0.0416 (5)
C19	0.7118 (2)	0.4012 (3)	0.34099 (14)	0.0607 (7)
C20	0.8370 (3)	0.5489 (6)	0.2923 (2)	0.1093 (14)
H20A	0.8004	0.6526	0.2822	0.131*
H20B	0.8302	0.4733	0.2556	0.131*
C21	0.9384 (4)	0.5893 (7)	0.3073 (3)	0.157 (2)
H21A	0.9443	0.6653	0.3434	0.236*
H21B	0.9644	0.6434	0.2711	0.236*
H21C	0.9739	0.4860	0.3175	0.236*
C22	0.8555 (2)	0.1969 (4)	0.42791 (15)	0.0608 (7)
C23	0.9301 (2)	0.2432 (6)	0.4718 (2)	0.0980 (12)
H23	0.9162	0.2978	0.5096	0.118*
C24	1.0256 (3)	0.2082 (8)	0.4597 (3)	0.158 (2)
H24	1.0756	0.2380	0.4898	0.190*
C25	1.0471 (4)	0.1317 (8)	0.4049 (4)	0.173 (3)
H25	1.1117	0.1126	0.3966	0.208*
C26	0.9744 (4)	0.0826 (6)	0.3620 (3)	0.147 (2)
H26	0.9895	0.0263	0.3248	0.176*
C27	0.8780 (3)	0.1146 (4)	0.37239 (18)	0.0861 (11)
H27	0.8287	0.0811	0.3424	0.103*
N1	0.58011 (14)	0.1277 (2)	0.56748 (9)	0.0444 (5)
O1	0.57068 (14)	0.0310 (2)	0.67859 (9)	0.0702 (6)
O2	0.72574 (14)	0.0126 (2)	0.62797 (9)	0.0634 (5)
O3	0.65793 (19)	0.4200 (3)	0.29378 (10)	0.0948 (8)
O4	0.80077 (15)	0.4669 (3)	0.34730 (10)	0.0734 (6)
S1	0.63858 (5)	0.10114 (8)	0.63854 (3)	0.0509 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0547 (16)	0.0481 (14)	0.0409 (13)	0.0008 (12)	−0.0055 (11)	0.0048 (11)
C2	0.0679 (19)	0.0637 (17)	0.0538 (16)	0.0102 (15)	0.0008 (14)	−0.0075 (14)
C3	0.109 (3)	0.068 (2)	0.0622 (19)	0.019 (2)	−0.0103 (19)	−0.0144 (16)
C4	0.132 (3)	0.0536 (18)	0.0597 (19)	−0.006 (2)	−0.030 (2)	0.0012 (15)
C5	0.089 (3)	0.078 (2)	0.072 (2)	−0.029 (2)	−0.0194 (18)	0.0139 (18)
C6	0.0603 (19)	0.0667 (18)	0.0591 (17)	−0.0064 (14)	−0.0056 (14)	0.0076 (14)
C7	0.0411 (15)	0.0379 (12)	0.0624 (16)	−0.0072 (11)	0.0091 (12)	−0.0121 (11)
C8	0.0522 (18)	0.0551 (15)	0.0735 (18)	−0.0113 (13)	0.0173 (14)	−0.0106 (14)
C9	0.0479 (19)	0.0633 (18)	0.101 (3)	−0.0128 (14)	0.0230 (17)	−0.0223 (18)
C10	0.0380 (17)	0.0687 (19)	0.105 (3)	−0.0051 (14)	−0.0003 (17)	−0.0231 (18)
C11	0.0417 (16)	0.0593 (16)	0.0779 (19)	−0.0003 (13)	−0.0036 (14)	−0.0114 (14)
C12	0.0425 (15)	0.0393 (12)	0.0587 (15)	−0.0049 (11)	0.0016 (12)	−0.0124 (11)
C13	0.0383 (14)	0.0390 (12)	0.0503 (14)	−0.0034 (10)	0.0006 (11)	−0.0076 (11)
C14	0.0518 (16)	0.0478 (13)	0.0485 (14)	0.0027 (12)	−0.0038 (12)	−0.0051 (11)
C15	0.0537 (16)	0.0427 (13)	0.0464 (14)	0.0003 (12)	0.0064 (12)	−0.0030 (11)
C16	0.0444 (15)	0.0412 (12)	0.0550 (15)	−0.0004 (11)	0.0078 (12)	−0.0024 (11)
C17	0.0397 (14)	0.0450 (13)	0.0484 (14)	0.0038 (11)	0.0029 (11)	0.0005 (11)
C18	0.0438 (15)	0.0358 (11)	0.0454 (13)	−0.0048 (10)	0.0055 (11)	−0.0058 (10)
C19	0.074 (2)	0.0547 (16)	0.0545 (17)	0.0057 (15)	0.0150 (15)	0.0020 (13)
C20	0.124 (4)	0.106 (3)	0.105 (3)	−0.003 (3)	0.052 (3)	0.041 (2)
C21	0.121 (4)	0.149 (4)	0.212 (6)	−0.001 (3)	0.091 (4)	0.068 (4)
C22	0.0500 (17)	0.0580 (16)	0.0767 (19)	0.0079 (13)	0.0211 (15)	0.0163 (14)
C23	0.046 (2)	0.137 (3)	0.111 (3)	−0.007 (2)	0.006 (2)	0.036 (3)
C24	0.046 (3)	0.217 (6)	0.214 (5)	0.001 (3)	0.016 (3)	0.115 (4)
C25	0.089 (3)	0.160 (5)	0.284 (7)	0.056 (3)	0.106 (3)	0.131 (4)
C26	0.158 (4)	0.086 (3)	0.215 (5)	0.055 (3)	0.137 (4)	0.052 (3)
C27	0.094 (3)	0.0635 (19)	0.108 (3)	0.0209 (17)	0.056 (2)	0.0117 (18)
N1	0.0435 (12)	0.0426 (10)	0.0477 (11)	−0.0024 (9)	0.0078 (9)	−0.0016 (9)
O1	0.0807 (14)	0.0662 (12)	0.0660 (12)	−0.0102 (10)	0.0219 (11)	0.0172 (10)
O2	0.0687 (11)	0.0556 (11)	0.0662 (12)	0.0211 (9)	0.0060 (9)	0.0091 (9)
O3	0.113 (2)	0.115 (2)	0.0549 (13)	−0.0079 (15)	−0.0046 (13)	0.0193 (13)
O4	0.0736 (15)	0.0710 (13)	0.0786 (14)	0.0018 (11)	0.0273 (11)	0.0238 (11)
S1	0.0585 (4)	0.0428 (3)	0.0519 (4)	0.0026 (3)	0.0086 (3)	0.0075 (3)

C1—C6	1.375 (4)	C15—C19	1.478 (4)
C1—C2	1.379 (4)	C16—C17	1.385 (3)
C1—S1	1.750 (3)	C16—C22	1.480 (3)
C2—C3	1.384 (4)	C17—C18	1.379 (3)
C2—H2	0.9300	C17—H17	0.9300
C3—C4	1.357 (5)	C18—N1	1.419 (3)
C3—H3	0.9300	C19—O3	1.202 (3)
C4—C5	1.361 (5)	C19—O4	1.326 (3)
C4—H4	0.9300	C20—O4	1.438 (4)
C5—C6	1.381 (4)	C20—C21	1.443 (6)
C5—H5	0.9300	C20—H20A	0.9700
C6—H6	0.9300	C20—H20B	0.9700
C7—C8	1.381 (3)	C21—H21A	0.9600
C7—C12	1.388 (4)	C21—H21B	0.9600
C7—N1	1.435 (3)	C21—H21C	0.9600
C8—C9	1.377 (4)	C22—C23	1.377 (5)
C8—H8	0.9300	C22—C27	1.383 (4)
C9—C10	1.379 (4)	C23—C24	1.385 (5)
C9—H9	0.9300	C23—H23	0.9300
C10—C11	1.371 (4)	C24—C25	1.345 (9)
C10—H10	0.9300	C24—H24	0.9300
C11—C12	1.391 (4)	C25—C26	1.354 (9)
C11—H11	0.9300	C25—H25	0.9300
C12—C13	1.441 (3)	C26—C27	1.383 (5)
C13—C14	1.377 (3)	C26—H26	0.9300
C13—C18	1.393 (3)	C27—H27	0.9300
C14—C15	1.381 (3)	N1—S1	1.655 (2)
C14—H14	0.9300	O1—S1	1.4103 (18)
C15—C16	1.409 (3)	O2—S1	1.4163 (18)
C6—C1—C2	121.6 (3)	C18—C17—H17	120.4
C6—C1—S1	119.2 (2)	C16—C17—H17	120.4
C2—C1—S1	119.1 (2)	C17—C18—C13	121.4 (2)
C1—C2—C3	118.3 (3)	C17—C18—N1	129.7 (2)
C1—C2—H2	120.9	C13—C18—N1	108.8 (2)
C3—C2—H2	120.9	O3—C19—O4	123.1 (3)
C4—C3—C2	120.3 (3)	O3—C19—C15	124.6 (3)
C4—C3—H3	119.8	O4—C19—C15	112.2 (3)
C2—C3—H3	119.8	O4—C20—C21	107.9 (4)
C3—C4—C5	121.1 (3)	O4—C20—H20A	110.1
C3—C4—H4	119.5	C21—C20—H20A	110.1
C5—C4—H4	119.5	O4—C20—H20B	110.1
C4—C5—C6	120.2 (3)	C21—C20—H20B	110.1
C4—C5—H5	119.9	H20A—C20—H20B	108.4
C6—C5—H5	119.9	C20—C21—H21A	109.5
C1—C6—C5	118.6 (3)	C20—C21—H21B	109.5
C1—C6—H6	120.7	H21A—C21—H21B	109.5
C5—C6—H6	120.7	C20—C21—H21C	109.5
C8—C7—C12	122.0 (2)	H21A—C21—H21C	109.5
C8—C7—N1	129.6 (3)	H21B—C21—H21C	109.5
C12—C7—N1	108.4 (2)	C23—C22—C27	119.0 (3)
C9—C8—C7	116.7 (3)	C23—C22—C16	119.6 (3)
C9—C8—H8	121.6	C27—C22—C16	121.4 (3)
C7—C8—H8	121.6	C22—C23—C24	119.9 (5)
C8—C9—C10	122.2 (3)	C22—C23—H23	120.1
C8—C9—H9	118.9	C24—C23—H23	120.1
C10—C9—H9	118.9	C25—C24—C23	120.9 (6)
C11—C10—C9	120.7 (3)	C25—C24—H24	119.5
C11—C10—H10	119.6	C23—C24—H24	119.5
C9—C10—H10	119.6	C24—C25—C26	119.7 (5)
C10—C11—C12	118.3 (3)	C24—C25—H25	120.1
C10—C11—H11	120.8	C26—C25—H25	120.1
C12—C11—H11	120.8	C25—C26—C27	121.1 (6)
C7—C12—C11	120.0 (2)	C25—C26—H26	119.4
C7—C12—C13	108.0 (2)	C27—C26—H26	119.4
C11—C12—C13	132.0 (3)	C22—C27—C26	119.4 (4)
C14—C13—C18	119.3 (2)	C22—C27—H27	120.3
C14—C13—C12	132.9 (2)	C26—C27—H27	120.3
C18—C13—C12	107.7 (2)	C18—N1—C7	106.97 (19)
C13—C14—C15	120.2 (2)	C18—N1—S1	122.35 (16)
C13—C14—H14	119.9	C7—N1—S1	123.77 (16)
C15—C14—H14	119.9	C19—O4—C20	117.6 (3)
C14—C15—C16	120.2 (2)	O1—S1—O2	120.49 (12)
C14—C15—C19	116.0 (2)	O1—S1—N1	106.47 (11)
C16—C15—C19	123.7 (2)	O2—S1—N1	106.51 (10)
C17—C16—C15	119.5 (2)	O1—S1—C1	109.47 (12)
C17—C16—C22	117.2 (2)	O2—S1—C1	108.49 (12)
C15—C16—C22	123.2 (2)	N1—S1—C1	104.18 (10)
C18—C17—C16	119.3 (2)
C6—C1—C2—C3	0.7 (4)	C14—C15—C19—O3	−31.9 (4)
S1—C1—C2—C3	−177.4 (2)	C16—C15—C19—O3	152.3 (3)
C1—C2—C3—C4	−0.2 (4)	C14—C15—C19—O4	144.6 (2)
C2—C3—C4—C5	−0.4 (5)	C16—C15—C19—O4	−31.2 (3)
C3—C4—C5—C6	0.6 (5)	C17—C16—C22—C23	−54.3 (4)
C2—C1—C6—C5	−0.6 (4)	C15—C16—C22—C23	129.2 (3)
S1—C1—C6—C5	177.5 (2)	C17—C16—C22—C27	122.7 (3)
C4—C5—C6—C1	−0.1 (4)	C15—C16—C22—C27	−53.8 (4)
C12—C7—C8—C9	−1.0 (4)	C27—C22—C23—C24	0.5 (5)
N1—C7—C8—C9	−178.3 (2)	C16—C22—C23—C24	177.6 (3)
C7—C8—C9—C10	0.8 (4)	C22—C23—C24—C25	1.0 (7)
C8—C9—C10—C11	−0.2 (4)	C23—C24—C25—C26	−2.3 (9)
C9—C10—C11—C12	−0.3 (4)	C24—C25—C26—C27	2.1 (9)
C8—C7—C12—C11	0.5 (4)	C23—C22—C27—C26	−0.8 (5)
N1—C7—C12—C11	178.4 (2)	C16—C22—C27—C26	−177.8 (3)
C8—C7—C12—C13	−179.2 (2)	C25—C26—C27—C22	−0.5 (7)
N1—C7—C12—C13	−1.3 (2)	C17—C18—N1—C7	179.8 (2)
C10—C11—C12—C7	0.1 (4)	C13—C18—N1—C7	−2.9 (2)
C10—C11—C12—C13	179.7 (2)	C17—C18—N1—S1	28.0 (3)
C7—C12—C13—C14	−179.2 (2)	C13—C18—N1—S1	−154.65 (16)
C11—C12—C13—C14	1.2 (4)	C8—C7—N1—C18	−179.8 (2)
C7—C12—C13—C18	−0.5 (3)	C12—C7—N1—C18	2.6 (2)
C11—C12—C13—C18	179.9 (2)	C8—C7—N1—S1	−28.5 (3)
C18—C13—C14—C15	−1.3 (3)	C12—C7—N1—S1	153.85 (16)
C12—C13—C14—C15	177.3 (2)	O3—C19—O4—C20	−6.6 (4)
C13—C14—C15—C16	2.9 (3)	C15—C19—O4—C20	176.9 (3)
C13—C14—C15—C19	−173.1 (2)	C21—C20—O4—C19	−172.3 (3)
C14—C15—C16—C17	−1.8 (3)	C18—N1—S1—O1	−174.87 (17)
C19—C15—C16—C17	173.8 (2)	C7—N1—S1—O1	38.1 (2)
C14—C15—C16—C22	174.6 (2)	C18—N1—S1—O2	−45.1 (2)
C19—C15—C16—C22	−9.7 (4)	C7—N1—S1—O2	167.82 (18)
C15—C16—C17—C18	−0.8 (3)	C18—N1—S1—C1	69.47 (19)
C22—C16—C17—C18	−177.5 (2)	C7—N1—S1—C1	−77.6 (2)
C16—C17—C18—C13	2.4 (3)	C6—C1—S1—O1	152.0 (2)
C16—C17—C18—N1	179.5 (2)	C2—C1—S1—O1	−29.9 (2)
C14—C13—C18—C17	−1.4 (3)	C6—C1—S1—O2	18.7 (2)
C12—C13—C18—C17	179.7 (2)	C2—C1—S1—O2	−163.2 (2)
C14—C13—C18—N1	−179.00 (19)	C6—C1—S1—N1	−94.5 (2)
C12—C13—C18—N1	2.1 (2)	C2—C1—S1—N1	83.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C25—H25···O2i	0.93	2.53	3.439 (5)	166
C11—H11···Cg2ii	0.93	2.83	3.752 (3)	172

Table 1

Hydrogen-bond geometry (, )

Cg2 is the centroid of the C1C6 ring.

DHA	DH	HA	D A	DHA
C25H25O2i	0.93	2.53	3.439(5)	166
C11H11Cg2ii	0.93	2.83	3.752(3)	172

Symmetry codes: (i) ; (ii) .