8-Chloro-4-[1-(phenyl­sulfonyl)­indol-3-yl]-3a,4,5,9b-tetra­hydro-3H-cyclo­penta­[c]­quinoline

In the title compound, C₂₆H₂₁ClN₂O₂S, the tetra­hydro­pyridine ring adopts a sofa conformation and the cyclo­pentene ring adopts an envelope conformation. In the crystal, centrosymmetrically related mol­ecules exist as N—H...O and C—H...O hydrogen-bonded dimers, and the molecular packing is stabilized by C—H...π and van der Waals interactions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.045
• wR factor = 0.124
• Data-to-parameter ratio = 18.6

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: 'ZORTEP (Zsolnai, 1997) and PLATON (Spek,1990)'; software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

8-Chloro-4-[1-(phenylsulfonyl)indol-3-yl]-3a,4,5,9 b-tetrahydro-3H- cyclopenta[c]quinoline

Crystal data

C26H21ClN2O2S	F(000) = 960
Mr = 460.96	Dx = 1.381 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 8685 reflections
a = 15.0064 (2) Å	θ = 1.9–28.3°
b = 9.4052 (2) Å	µ = 0.29 mm^−1
c = 15.7077 (2) Å	T = 293 K
β = 91.093 (1)°	Block, colourless
V = 2216.55 (6) Å^3	0.40 × 0.18 × 0.14 mm
Z = 4

Data collection

Siemens SMART CCD area-detector diffractometer	4073 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.031
Graphite monochromator	θmax = 28.3°, θmin = 1.9°
ω scans	h = −19→19
14665 measured reflections	k = −8→12
5441 independent reflections	l = −20→20

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0576P)^2 + 0.724P] where P = (Fo^2 + 2Fc^2)/3
5441 reflections	(Δ/σ)max = 0.001
293 parameters	Δρmax = 0.46 e Å^−3
0 restraints	Δρmin = −0.38 e Å^−3

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
Cl1	0.34650 (4)	0.38433 (7)	−0.05889 (3)	0.05846 (18)
N1	0.38942 (10)	0.37098 (17)	0.31710 (9)	0.0358 (3)
H1	0.4420 (14)	0.401 (2)	0.3331 (13)	0.043 (6)*
C1	0.37722 (10)	0.37470 (18)	0.22803 (10)	0.0300 (3)
C2	0.42888 (11)	0.4666 (2)	0.17900 (11)	0.0333 (4)
H2	0.4710	0.5247	0.2057	0.040*
C3	0.41811 (11)	0.4720 (2)	0.09120 (11)	0.0360 (4)
H3	0.4515	0.5350	0.0591	0.043*
C4	0.35687 (12)	0.3821 (2)	0.05201 (11)	0.0377 (4)
C5	0.30437 (12)	0.2928 (2)	0.09952 (11)	0.0376 (4)
H5	0.2632	0.2340	0.0720	0.045*
C6	0.31210 (11)	0.28950 (19)	0.18830 (10)	0.0326 (4)
C7	0.24643 (12)	0.2033 (2)	0.24014 (11)	0.0377 (4)
H7	0.2437	0.1053	0.2190	0.045*
C8	0.15457 (13)	0.2704 (3)	0.23583 (15)	0.0541 (6)
H8	0.1183	0.2701	0.1872	0.065*
C9	0.13180 (14)	0.3289 (3)	0.30791 (16)	0.0605 (6)
H9	0.0782	0.3765	0.3156	0.073*
C10	0.20122 (13)	0.3106 (3)	0.37652 (14)	0.0518 (5)
H10A	0.1755	0.2726	0.4280	0.062*
H10B	0.2304	0.4002	0.3897	0.062*
C11	0.26683 (11)	0.2040 (2)	0.33723 (11)	0.0357 (4)
H11	0.2533	0.1093	0.3596	0.043*
C12	0.36544 (11)	0.2356 (2)	0.35653 (10)	0.0331 (4)
H12	0.4015	0.1601	0.3314	0.040*
C13	0.38334 (11)	0.2380 (2)	0.45087 (10)	0.0338 (4)
C14	0.39474 (12)	0.3514 (2)	0.50221 (11)	0.0379 (4)
H14	0.3933	0.4457	0.4843	0.046*
N15	0.40929 (10)	0.30609 (18)	0.58815 (9)	0.0393 (4)
C16	0.40227 (11)	0.1551 (2)	0.58807 (11)	0.0363 (4)
C17	0.41234 (13)	0.0576 (3)	0.65434 (12)	0.0466 (5)
H17	0.4225	0.0870	0.7102	0.056*
C18	0.40656 (14)	−0.0851 (3)	0.63326 (14)	0.0519 (5)
H18	0.4119	−0.1528	0.6762	0.062*
C19	0.39307 (14)	−0.1300 (2)	0.54965 (15)	0.0503 (5)
H19	0.3898	−0.2267	0.5377	0.060*
C20	0.38452 (13)	−0.0327 (2)	0.48424 (13)	0.0428 (4)
H20	0.3764	−0.0631	0.4283	0.051*
C21	0.38823 (11)	0.1115 (2)	0.50338 (11)	0.0345 (4)
S22	0.36630 (3)	0.40537 (6)	0.66506 (3)	0.04312 (14)
O23	0.39627 (10)	0.54714 (17)	0.64927 (10)	0.0555 (4)
O24	0.38853 (11)	0.33714 (19)	0.74343 (8)	0.0582 (4)
C25	0.25011 (13)	0.3965 (2)	0.64686 (12)	0.0453 (5)
C26	0.20698 (16)	0.2694 (3)	0.66350 (17)	0.0630 (6)
H26	0.2383	0.1925	0.6863	0.076*
C27	0.11723 (18)	0.2589 (3)	0.6456 (2)	0.0789 (9)
H27	0.0875	0.1742	0.6563	0.095*
C28	0.07144 (18)	0.3720 (4)	0.6123 (2)	0.0809 (9)
H28	0.0109	0.3633	0.5998	0.097*
C29	0.11430 (19)	0.4987 (4)	0.5971 (2)	0.0846 (9)
H29	0.0823	0.5758	0.5756	0.102*
C30	0.20511 (17)	0.5120 (3)	0.61394 (17)	0.0642 (6)
H30	0.2347	0.5968	0.6032	0.077*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0636 (3)	0.0847 (4)	0.0271 (2)	−0.0170 (3)	0.0008 (2)	0.0028 (2)
N1	0.0353 (8)	0.0434 (9)	0.0284 (7)	−0.0086 (7)	−0.0033 (6)	0.0020 (6)
C1	0.0274 (8)	0.0359 (9)	0.0268 (7)	0.0023 (6)	0.0000 (6)	0.0003 (7)
C2	0.0263 (8)	0.0404 (10)	0.0333 (8)	−0.0017 (7)	0.0010 (6)	−0.0006 (7)
C3	0.0311 (8)	0.0443 (11)	0.0328 (8)	−0.0004 (7)	0.0075 (6)	0.0033 (8)
C4	0.0364 (9)	0.0498 (11)	0.0269 (8)	0.0023 (8)	0.0023 (6)	−0.0003 (8)
C5	0.0380 (9)	0.0441 (11)	0.0307 (8)	−0.0043 (8)	−0.0044 (7)	−0.0022 (8)
C6	0.0315 (8)	0.0350 (9)	0.0313 (8)	−0.0009 (7)	−0.0011 (6)	0.0025 (7)
C7	0.0380 (9)	0.0412 (10)	0.0337 (8)	−0.0097 (8)	−0.0070 (7)	0.0068 (8)
C8	0.0312 (9)	0.0758 (16)	0.0551 (12)	−0.0116 (10)	−0.0090 (8)	0.0299 (12)
C9	0.0339 (10)	0.0759 (17)	0.0721 (15)	0.0060 (10)	0.0058 (10)	0.0229 (13)
C10	0.0385 (10)	0.0641 (14)	0.0532 (12)	0.0015 (10)	0.0075 (9)	0.0015 (11)
C11	0.0338 (8)	0.0419 (10)	0.0314 (8)	−0.0052 (7)	−0.0019 (6)	0.0075 (7)
C12	0.0331 (8)	0.0387 (10)	0.0273 (8)	−0.0001 (7)	−0.0022 (6)	0.0036 (7)
C13	0.0308 (8)	0.0421 (10)	0.0284 (8)	−0.0009 (7)	−0.0020 (6)	0.0032 (7)
C14	0.0420 (9)	0.0419 (10)	0.0297 (8)	−0.0052 (8)	−0.0022 (7)	0.0077 (8)
N15	0.0440 (8)	0.0455 (9)	0.0283 (7)	−0.0069 (7)	−0.0024 (6)	0.0031 (7)
C16	0.0327 (8)	0.0434 (10)	0.0329 (8)	−0.0016 (7)	−0.0018 (7)	0.0060 (8)
C17	0.0437 (10)	0.0610 (14)	0.0351 (9)	0.0018 (9)	−0.0027 (8)	0.0125 (9)
C18	0.0473 (11)	0.0554 (14)	0.0531 (12)	0.0057 (9)	0.0007 (9)	0.0241 (10)
C19	0.0452 (11)	0.0423 (12)	0.0634 (13)	0.0022 (9)	0.0016 (9)	0.0099 (10)
C20	0.0403 (10)	0.0451 (11)	0.0430 (10)	0.0019 (8)	−0.0030 (8)	0.0009 (9)
C21	0.0283 (8)	0.0419 (10)	0.0332 (8)	−0.0004 (7)	−0.0018 (6)	0.0060 (7)
S22	0.0479 (3)	0.0504 (3)	0.0308 (2)	−0.0154 (2)	−0.00353 (18)	−0.0060 (2)
O23	0.0629 (9)	0.0486 (9)	0.0550 (9)	−0.0218 (7)	−0.0020 (7)	−0.0097 (7)
O24	0.0724 (10)	0.0728 (11)	0.0290 (7)	−0.0149 (8)	−0.0086 (6)	−0.0018 (7)
C25	0.0432 (10)	0.0539 (13)	0.0388 (9)	−0.0105 (9)	0.0046 (8)	−0.0097 (9)
C26	0.0513 (13)	0.0578 (15)	0.0802 (17)	−0.0131 (11)	0.0119 (11)	−0.0060 (12)
C27	0.0518 (14)	0.079 (2)	0.106 (2)	−0.0218 (14)	0.0172 (14)	−0.0238 (17)
C28	0.0453 (13)	0.111 (3)	0.087 (2)	−0.0101 (15)	0.0034 (13)	−0.0264 (19)
C29	0.0609 (17)	0.099 (2)	0.093 (2)	0.0107 (16)	−0.0046 (15)	0.0064 (18)
C30	0.0566 (14)	0.0663 (16)	0.0698 (15)	−0.0060 (12)	0.0004 (11)	0.0037 (13)

Geometric parameters (Å, º)

Cl1—C4	1.7462 (18)	C13—C21	1.449 (2)
N1—C1	1.408 (2)	C14—N15	1.428 (2)
N1—C12	1.464 (2)	C14—H14	0.93
N1—H1	0.87 (2)	N15—C16	1.424 (3)
C1—C2	1.401 (2)	N15—S22	1.6665 (17)
C1—C6	1.401 (2)	C16—C17	1.393 (3)
C2—C3	1.386 (2)	C16—C21	1.404 (2)
C2—H2	0.93	C17—C18	1.385 (3)
C3—C4	1.384 (3)	C17—H17	0.93
C3—H3	0.93	C18—C19	1.391 (3)
C4—C5	1.380 (3)	C18—H18	0.93
C5—C6	1.397 (2)	C19—C20	1.380 (3)
C5—H5	0.93	C19—H19	0.93
C6—C7	1.524 (2)	C20—C21	1.390 (3)
C7—C8	1.516 (3)	C20—H20	0.93
C7—C11	1.550 (2)	S22—O24	1.4223 (15)
C7—H7	0.98	S22—O23	1.4303 (16)
C8—C9	1.310 (3)	S22—C25	1.763 (2)
C8—H8	0.93	C25—C30	1.375 (3)
C9—C10	1.494 (3)	C25—C26	1.387 (3)
C9—H9	0.93	C26—C27	1.374 (3)
C10—C11	1.542 (3)	C26—H26	0.93
C10—H10A	0.97	C27—C28	1.365 (4)
C10—H10B	0.97	C27—H27	0.93
C11—C12	1.534 (2)	C28—C29	1.378 (4)
C11—H11	0.98	C28—H28	0.93
C12—C13	1.501 (2)	C29—C30	1.389 (4)
C12—H12	0.98	C29—H29	0.93
C13—C14	1.346 (3)	C30—H30	0.93
C1—N1—C12	114.44 (14)	C14—C13—C21	107.78 (15)
C1—N1—H1	112.3 (14)	C14—C13—C12	128.44 (17)
C12—N1—H1	112.9 (14)	C21—C13—C12	123.75 (16)
C2—C1—C6	119.76 (15)	C13—C14—N15	110.18 (16)
C2—C1—N1	119.91 (15)	C13—C14—H14	124.9
C6—C1—N1	120.31 (15)	N15—C14—H14	124.9
C3—C2—C1	120.94 (16)	C16—N15—C14	106.67 (14)
C3—C2—H2	119.5	C16—N15—S22	121.99 (12)
C1—C2—H2	119.5	C14—N15—S22	117.61 (14)
C4—C3—C2	118.93 (16)	C17—C16—C21	121.88 (19)
C4—C3—H3	120.5	C17—C16—N15	130.44 (18)
C2—C3—H3	120.5	C21—C16—N15	107.56 (15)
C5—C4—C3	120.79 (16)	C18—C17—C16	116.98 (19)
C5—C4—Cl1	120.39 (14)	C18—C17—H17	121.5
C3—C4—Cl1	118.81 (14)	C16—C17—H17	121.5
C4—C5—C6	121.06 (16)	C19—C18—C17	121.83 (19)
C4—C5—H5	119.5	C19—C18—H18	119.1
C6—C5—H5	119.5	C17—C18—H18	119.1
C5—C6—C1	118.39 (15)	C20—C19—C18	120.8 (2)
C5—C6—C7	120.20 (15)	C20—C19—H19	119.6
C1—C6—C7	121.26 (15)	C18—C19—H19	119.6
C8—C7—C6	110.58 (15)	C19—C20—C21	118.89 (19)
C8—C7—C11	101.80 (16)	C19—C20—H20	120.6
C6—C7—C11	113.96 (14)	C21—C20—H20	120.6
C8—C7—H7	110.1	C20—C21—C16	119.63 (17)
C6—C7—H7	110.1	C20—C21—C13	132.59 (17)
C11—C7—H7	110.1	C16—C21—C13	107.74 (16)
C9—C8—C7	112.83 (18)	O24—S22—O23	120.09 (9)
C9—C8—H8	123.6	O24—S22—N15	106.68 (10)
C7—C8—H8	123.6	O23—S22—N15	105.62 (9)
C8—C9—C10	112.7 (2)	O24—S22—C25	109.50 (10)
C8—C9—H9	123.7	O23—S22—C25	109.22 (10)
C10—C9—H9	123.7	N15—S22—C25	104.55 (8)
C9—C10—C11	103.15 (18)	C30—C25—C26	121.6 (2)
C9—C10—H10A	111.1	C30—C25—S22	120.05 (17)
C11—C10—H10A	111.1	C26—C25—S22	118.28 (18)
C9—C10—H10B	111.1	C27—C26—C25	118.9 (3)
C11—C10—H10B	111.1	C27—C26—H26	120.6
H10A—C10—H10B	109.1	C25—C26—H26	120.6
C12—C11—C10	114.58 (16)	C28—C27—C26	120.4 (3)
C12—C11—C7	111.53 (14)	C28—C27—H27	119.8
C10—C11—C7	106.32 (15)	C26—C27—H27	119.8
C12—C11—H11	108.1	C27—C28—C29	120.5 (3)
C10—C11—H11	108.1	C27—C28—H28	119.8
C7—C11—H11	108.1	C29—C28—H28	119.8
N1—C12—C13	111.33 (14)	C28—C29—C30	120.3 (3)
N1—C12—C11	109.19 (14)	C28—C29—H29	119.8
C13—C12—C11	110.60 (13)	C30—C29—H29	119.8
N1—C12—H12	108.6	C25—C30—C29	118.3 (3)
C13—C12—H12	108.6	C25—C30—H30	120.9
C11—C12—H12	108.6	C29—C30—H30	120.9
C12—N1—C1—C2	−153.40 (16)	C13—C14—N15—C16	−2.6 (2)
C12—N1—C1—C6	28.2 (2)	C13—C14—N15—S22	−143.88 (14)
C6—C1—C2—C3	−1.6 (3)	C14—N15—C16—C17	178.61 (19)
N1—C1—C2—C3	179.94 (16)	S22—N15—C16—C17	−42.2 (3)
C1—C2—C3—C4	−1.7 (3)	C14—N15—C16—C21	2.78 (19)
C2—C3—C4—C5	2.9 (3)	S22—N15—C16—C21	142.02 (13)
C2—C3—C4—Cl1	−177.58 (14)	C21—C16—C17—C18	−0.9 (3)
C3—C4—C5—C6	−0.7 (3)	N15—C16—C17—C18	−176.25 (19)
Cl1—C4—C5—C6	179.78 (14)	C16—C17—C18—C19	1.2 (3)
C4—C5—C6—C1	−2.7 (3)	C17—C18—C19—C20	−0.3 (3)
C4—C5—C6—C7	172.90 (18)	C18—C19—C20—C21	−1.0 (3)
C2—C1—C6—C5	3.8 (3)	C19—C20—C21—C16	1.2 (3)
N1—C1—C6—C5	−177.81 (16)	C19—C20—C21—C13	178.69 (18)
C2—C1—C6—C7	−171.74 (16)	C17—C16—C21—C20	−0.3 (3)
N1—C1—C6—C7	6.7 (3)	N15—C16—C21—C20	175.98 (16)
C5—C6—C7—C8	−69.1 (2)	C17—C16—C21—C13	−178.31 (16)
C1—C6—C7—C8	106.35 (19)	N15—C16—C21—C13	−2.04 (19)
C5—C6—C7—C11	176.97 (16)	C14—C13—C21—C20	−177.18 (19)
C1—C6—C7—C11	−7.6 (3)	C12—C13—C21—C20	4.7 (3)
C6—C7—C8—C9	−109.2 (2)	C14—C13—C21—C16	0.48 (19)
C11—C7—C8—C9	12.2 (2)	C12—C13—C21—C16	−177.67 (15)
C7—C8—C9—C10	−1.7 (3)	C16—N15—S22—O24	43.94 (16)
C8—C9—C10—C11	−9.8 (3)	C14—N15—S22—O24	179.04 (13)
C9—C10—C11—C12	140.41 (17)	C16—N15—S22—O23	172.78 (14)
C9—C10—C11—C7	16.7 (2)	C14—N15—S22—O23	−52.12 (15)
C8—C7—C11—C12	−142.89 (16)	C16—N15—S22—C25	−72.03 (15)
C6—C7—C11—C12	−23.8 (2)	C14—N15—S22—C25	63.08 (15)
C8—C7—C11—C10	−17.3 (2)	O24—S22—C25—C30	139.49 (19)
C6—C7—C11—C10	101.73 (18)	O23—S22—C25—C30	6.1 (2)
C1—N1—C12—C13	177.93 (14)	N15—S22—C25—C30	−106.53 (19)
C1—N1—C12—C11	−59.67 (18)	O24—S22—C25—C26	−42.9 (2)
C10—C11—C12—N1	−64.56 (19)	O23—S22—C25—C26	−176.32 (17)
C7—C11—C12—N1	56.3 (2)	N15—S22—C25—C26	71.04 (19)
C10—C11—C12—C13	58.3 (2)	C30—C25—C26—C27	0.7 (4)
C7—C11—C12—C13	179.11 (16)	S22—C25—C26—C27	−176.8 (2)
N1—C12—C13—C14	18.7 (2)	C25—C26—C27—C28	−0.2 (4)
C11—C12—C13—C14	−102.9 (2)	C26—C27—C28—C29	−0.9 (5)
N1—C12—C13—C21	−163.60 (15)	C27—C28—C29—C30	1.4 (5)
C11—C12—C13—C21	74.8 (2)	C26—C25—C30—C29	−0.2 (4)
C21—C13—C14—N15	1.3 (2)	S22—C25—C30—C29	177.3 (2)
C12—C13—C14—N15	179.33 (16)	C28—C29—C30—C25	−0.9 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O23^i	0.87 (2)	2.49 (2)	3.339 (2)	167
C2—H2···O24^i	0.93	2.59	3.503 (2)	168
C17—H17···O24	0.93	2.46	3.003 (3)	117
C30—H30···O23	0.93	2.56	2.930 (3)	104

Symmetry code: (i) −x+1, −y+1, −z+1.