The conversion of a pyrrole trimer derivative into a 4,5,6,7-tetra­hydro-4-­(pyrrol-2-yl)indol-7-yl­tosyl­aminoindole

Vilsmeier formyl­ation of trans-1-(4-methyl­phenyl­sulfonyl)-2,5-bis(pyrrol-2-yl)­pyrrolidine leads to cleavage of the central ring then a reclosure resulting in the formation of trans-N-[2-formyl-4-(5-formyl­pyrrol-2-yl)-4,5,6,7-tetra­hydro­indol-7-yl]­toluene­sulfon­amide, C₂₁H₂₁N₃O₄S.

Computing details

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1993); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1995); program(s) used to solve structure: SIR92 (Altomare et al. 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: TEXSAN.

(2)

Crystal data

C21H21N3O4S	F(000) = 864
Mr = 411.47	Dx = 1.398 Mg m^−3
Orthorhombic, Pna21	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: P 2c -2n	Cell parameters from 17 reflections
a = 11.788 (2) Å	θ = 38.5–39.8°
b = 6.6204 (16) Å	µ = 1.76 mm^−1
c = 25.057 (3) Å	T = 293 K
V = 1955.5 (6) Å^3	Tabular, pink
Z = 4	0.50 × 0.40 × 0.15 mm

Data collection

Rigaku AFC5R diffractometer	1919 reflections with I > 2σ(I)
Radiation source: Rigaku rotating anode	Rint = 0.000
Graphite monochromator	θmax = 79.1°, θmin = 3.5°
ω–2θ scans	h = 0→14
Absorption correction: ψ scans (north et al., 1968)	k = 0→8
Tmin = 0.544, Tmax = 0.768	l = −31→0
2102 measured reflections	3 standard reflections every 150 reflections
2102 independent reflections	intensity decay: 1.2%

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.107	H-atom parameters constrained
S = 1.07	Calculated w = 1/[σ^2(Fo^2) + (0.065P)^2 + 0.3269P] where P = (Fo^2 + 2Fc^2)/3
2102 reflections	(Δ/σ)max = 0.001
264 parameters	Δρmax = 0.22 e Å^−3
1 restraint	Δρmin = −0.20 e Å^−3

Special details

Experimental. The scan width was (0.94 + 0.30tanθ)° with an ω scan speed of 8° per minute (up to 4 scans to achieve I/σ(I) > 10). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1.

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
S1	0.21915 (7)	−0.11439 (13)	0.40862 (3)	0.0452 (2)
O1	0.2935 (2)	−0.2699 (4)	0.38861 (12)	0.0599 (7)
O2	0.1228 (2)	−0.1706 (5)	0.43971 (11)	0.0641 (8)
O3	−0.2094 (2)	−0.4180 (4)	0.25519 (11)	0.0519 (6)
O4	0.3506 (4)	−0.0257 (7)	0.11228 (16)	0.0953 (13)
N1	0.1756 (3)	0.0101 (6)	0.35761 (11)	0.0529 (8)
H1	0.2182	0.0078	0.3298	0.063*
N2	−0.0576 (2)	−0.1086 (4)	0.30046 (11)	0.0387 (6)
H2	−0.0721	−0.1917	0.3259	0.046*
N3	0.2003 (2)	0.2209 (5)	0.17757 (12)	0.0462 (7)
H3	0.2169	0.1140	0.1954	0.055*
C1	0.0696 (3)	0.1280 (5)	0.35373 (14)	0.0424 (7)
H1A	0.0228	0.1041	0.3854	0.051*
C2	0.0919 (4)	0.3553 (6)	0.34740 (18)	0.0599 (11)
H2A	0.0207	0.4278	0.3502	0.072*
H2B	0.1409	0.4007	0.3761	0.072*
C3	0.1474 (4)	0.4046 (6)	0.29404 (16)	0.0553 (9)
H3A	0.2169	0.3273	0.2905	0.066*
H3B	0.1672	0.5468	0.2932	0.066*
C4	0.0690 (3)	0.3568 (5)	0.24688 (16)	0.0461 (8)
H4	0.0098	0.4607	0.2464	0.055*
C5	0.0102 (3)	0.1553 (5)	0.25561 (13)	0.0394 (7)
C6	0.0069 (3)	0.0602 (4)	0.30458 (13)	0.0376 (6)
C7	−0.0532 (3)	0.0384 (5)	0.22032 (14)	0.0422 (7)
H7	−0.0646	0.0649	0.1843	0.051*
C8	−0.0962 (3)	−0.1252 (5)	0.24869 (13)	0.0393 (7)
C9	−0.1691 (3)	−0.2796 (5)	0.22912 (13)	0.0434 (7)
H9	−0.1877	−0.2748	0.1931	0.052*
C10	0.1285 (3)	0.3660 (5)	0.19395 (15)	0.0461 (8)
C11	0.1241 (4)	0.5107 (7)	0.15453 (19)	0.0665 (12)
H11	0.0806	0.6278	0.1551	0.080*
C12	0.1959 (4)	0.4509 (8)	0.11400 (19)	0.0679 (12)
H12	0.2098	0.5218	0.0826	0.082*
C13	0.2435 (3)	0.2687 (7)	0.12794 (14)	0.0532 (9)
C14	0.3179 (4)	0.1401 (9)	0.09877 (17)	0.0672 (12)
H14	0.3439	0.1881	0.0661	0.081*
C15	0.3036 (3)	0.0469 (5)	0.44833 (13)	0.0409 (7)
C16	0.4077 (3)	−0.0159 (6)	0.46530 (15)	0.0486 (8)
H16	0.4363	−0.1404	0.4546	0.058*
C17	0.4704 (3)	0.1085 (7)	0.49879 (17)	0.0578 (10)
H17	0.5409	0.0648	0.5108	0.069*
C18	0.4309 (3)	0.2954 (6)	0.51467 (14)	0.0502 (8)
C19	0.3263 (5)	0.3549 (7)	0.49646 (19)	0.0701 (13)
H19	0.2986	0.4817	0.5058	0.084*
C20	0.2614 (4)	0.2302 (8)	0.46457 (19)	0.0705 (13)
H20	0.1892	0.2703	0.4541	0.085*
C21	0.4998 (5)	0.4280 (8)	0.5517 (2)	0.0766 (14)
H21A	0.5542	0.5033	0.5314	0.115*
H21B	0.5386	0.3450	0.5773	0.115*
H21C	0.4502	0.5197	0.5701	0.115*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0459 (4)	0.0519 (4)	0.0379 (3)	−0.0048 (3)	−0.0023 (4)	−0.0088 (4)
O1	0.0728 (18)	0.0518 (15)	0.0550 (14)	0.0041 (12)	−0.0077 (13)	−0.0121 (12)
O2	0.0577 (16)	0.0798 (19)	0.0547 (16)	−0.0191 (15)	0.0007 (13)	0.0010 (15)
O3	0.0545 (14)	0.0518 (13)	0.0496 (13)	−0.0133 (12)	0.0049 (11)	−0.0079 (12)
O4	0.109 (3)	0.105 (3)	0.071 (2)	0.024 (3)	0.034 (2)	0.012 (2)
N1	0.0464 (16)	0.080 (2)	0.0322 (13)	0.0037 (16)	−0.0029 (12)	−0.0086 (14)
N2	0.0389 (13)	0.0378 (12)	0.0393 (13)	−0.0030 (10)	0.0009 (11)	0.0044 (11)
N3	0.0481 (15)	0.0498 (16)	0.0407 (13)	−0.0022 (13)	0.0025 (12)	0.0119 (12)
C1	0.0430 (18)	0.0459 (17)	0.0382 (15)	−0.0032 (14)	0.0048 (13)	−0.0064 (14)
C2	0.073 (3)	0.051 (2)	0.056 (2)	−0.0121 (19)	0.013 (2)	−0.0173 (18)
C3	0.064 (2)	0.0423 (18)	0.060 (2)	−0.0150 (16)	0.0084 (19)	−0.0072 (17)
C4	0.0437 (18)	0.0342 (15)	0.060 (2)	0.0010 (13)	0.0059 (16)	0.0079 (15)
C5	0.0309 (15)	0.0405 (15)	0.0468 (17)	0.0032 (12)	0.0026 (13)	0.0049 (13)
C6	0.0339 (15)	0.0365 (14)	0.0425 (16)	0.0006 (12)	0.0023 (13)	−0.0002 (13)
C7	0.0369 (15)	0.0488 (17)	0.0409 (16)	0.0040 (14)	−0.0003 (13)	0.0080 (14)
C8	0.0352 (15)	0.0427 (16)	0.0398 (15)	0.0036 (12)	0.0001 (12)	−0.0010 (14)
C9	0.0408 (17)	0.0488 (18)	0.0406 (16)	0.0026 (14)	−0.0010 (13)	−0.0059 (15)
C10	0.0412 (17)	0.0424 (17)	0.055 (2)	−0.0065 (14)	−0.0029 (15)	0.0140 (15)
C11	0.064 (2)	0.060 (2)	0.075 (3)	0.0014 (19)	−0.009 (2)	0.030 (2)
C12	0.068 (3)	0.080 (3)	0.056 (2)	−0.012 (2)	−0.004 (2)	0.032 (2)
C13	0.053 (2)	0.066 (2)	0.0406 (16)	−0.0153 (18)	−0.0020 (16)	0.0137 (17)
C14	0.070 (3)	0.089 (3)	0.0426 (19)	−0.018 (2)	0.0086 (19)	0.004 (2)
C15	0.0411 (16)	0.0477 (17)	0.0340 (14)	−0.0016 (14)	−0.0025 (12)	−0.0062 (13)
C16	0.0474 (18)	0.053 (2)	0.0457 (17)	0.0051 (15)	−0.0062 (15)	0.0001 (16)
C17	0.0421 (19)	0.074 (2)	0.057 (2)	−0.0001 (17)	−0.0123 (17)	0.002 (2)
C18	0.055 (2)	0.058 (2)	0.0381 (16)	−0.0137 (17)	−0.0061 (15)	0.0017 (15)
C19	0.091 (3)	0.059 (2)	0.060 (2)	0.017 (2)	−0.023 (2)	−0.022 (2)
C20	0.064 (2)	0.079 (3)	0.069 (3)	0.025 (2)	−0.028 (2)	−0.033 (2)
C21	0.089 (3)	0.080 (3)	0.061 (3)	−0.026 (3)	−0.020 (2)	−0.008 (2)

Geometric parameters (Å, º)

S1—O2	1.427 (3)	C5—C7	1.392 (5)
S1—O1	1.443 (3)	C7—C8	1.392 (5)
S1—N1	1.605 (3)	C7—H7	0.9300
S1—C15	1.767 (3)	C8—C9	1.422 (5)
O3—C9	1.222 (4)	C9—H9	0.9300
O4—C14	1.212 (7)	C10—C11	1.377 (5)
N1—C1	1.476 (5)	C11—C12	1.380 (7)
N1—H1	0.8600	C11—H11	0.9300
N2—C6	1.356 (4)	C12—C13	1.376 (7)
N2—C8	1.379 (4)	C12—H12	0.9300
N2—H2	0.8600	C13—C14	1.423 (7)
N3—C10	1.344 (5)	C14—H14	0.9300
N3—C13	1.381 (5)	C15—C16	1.364 (5)
N3—H3	0.8600	C15—C20	1.373 (6)
C1—C6	1.505 (5)	C16—C17	1.389 (5)
C1—C2	1.536 (5)	C16—H16	0.9300
C1—H1A	0.9800	C17—C18	1.381 (6)
C2—C3	1.524 (6)	C17—H17	0.9300
C2—H2A	0.9700	C18—C19	1.372 (6)
C2—H2B	0.9700	C18—C21	1.514 (6)
C3—C4	1.533 (6)	C19—C20	1.380 (6)
C3—H3A	0.9700	C19—H19	0.9300
C3—H3B	0.9700	C20—H20	0.9300
C4—C10	1.501 (5)	C21—H21A	0.9600
C4—C5	1.519 (4)	C21—H21B	0.9600
C4—H4	0.9800	C21—H21C	0.9600
C5—C6	1.380 (5)
O2—S1—O1	119.18 (19)	C5—C7—H7	126.2
O2—S1—N1	108.29 (18)	N2—C8—C7	107.3 (3)
O1—S1—N1	106.52 (17)	N2—C8—C9	125.5 (3)
O2—S1—C15	107.38 (16)	C7—C8—C9	127.1 (3)
O1—S1—C15	106.56 (16)	O3—C9—C8	126.1 (3)
N1—S1—C15	108.57 (18)	O3—C9—H9	116.9
C1—N1—S1	126.5 (2)	C8—C9—H9	116.9
C1—N1—H1	116.7	N3—C10—C11	107.5 (4)
S1—N1—H1	116.7	N3—C10—C4	122.3 (3)
C6—N2—C8	108.8 (3)	C11—C10—C4	130.1 (4)
C6—N2—H2	125.6	C10—C11—C12	107.8 (4)
C8—N2—H2	125.6	C10—C11—H11	126.1
C10—N3—C13	110.1 (3)	C12—C11—H11	126.1
C10—N3—H3	124.9	C13—C12—C11	108.3 (4)
C13—N3—H3	124.9	C13—C12—H12	125.8
N1—C1—C6	108.2 (3)	C11—C12—H12	125.8
N1—C1—C2	112.3 (3)	C12—C13—N3	106.2 (4)
C6—C1—C2	107.0 (3)	C12—C13—C14	130.2 (4)
N1—C1—H1A	109.8	N3—C13—C14	123.6 (4)
C6—C1—H1A	109.8	O4—C14—C13	126.4 (4)
C2—C1—H1A	109.8	O4—C14—H14	116.8
C3—C2—C1	112.0 (3)	C13—C14—H14	116.8
C3—C2—H2A	109.2	C16—C15—C20	120.2 (3)
C1—C2—H2A	109.2	C16—C15—S1	119.9 (3)
C3—C2—H2B	109.2	C20—C15—S1	119.8 (3)
C1—C2—H2B	109.2	C15—C16—C17	119.1 (4)
H2A—C2—H2B	107.9	C15—C16—H16	120.4
C2—C3—C4	111.9 (3)	C17—C16—H16	120.4
C2—C3—H3A	109.2	C18—C17—C16	121.7 (4)
C4—C3—H3A	109.2	C18—C17—H17	119.1
C2—C3—H3B	109.2	C16—C17—H17	119.1
C4—C3—H3B	109.2	C19—C18—C17	117.7 (3)
H3A—C3—H3B	107.9	C19—C18—C21	121.3 (4)
C10—C4—C5	112.1 (3)	C17—C18—C21	121.0 (4)
C10—C4—C3	113.0 (3)	C18—C19—C20	121.2 (4)
C5—C4—C3	110.2 (3)	C18—C19—H19	119.4
C10—C4—H4	107.1	C20—C19—H19	119.4
C5—C4—H4	107.1	C15—C20—C19	120.0 (4)
C3—C4—H4	107.1	C15—C20—H20	120.0
C6—C5—C7	107.2 (3)	C19—C20—H20	120.0
C6—C5—C4	122.8 (3)	C18—C21—H21A	109.5
C7—C5—C4	129.9 (3)	C18—C21—H21B	109.5
N2—C6—C5	108.9 (3)	H21A—C21—H21B	109.5
N2—C6—C1	125.7 (3)	C18—C21—H21C	109.5
C5—C6—C1	125.3 (3)	H21A—C21—H21C	109.5
C8—C7—C5	107.7 (3)	H21B—C21—H21C	109.5
C8—C7—H7	126.2
O2—S1—N1—C1	25.9 (4)	C13—N3—C10—C11	0.2 (4)
O1—S1—N1—C1	155.3 (3)	C13—N3—C10—C4	−179.4 (3)
C15—S1—N1—C1	−90.3 (3)	C5—C4—C10—N3	−50.6 (5)
S1—N1—C1—C6	−128.0 (3)	C3—C4—C10—N3	74.7 (4)
S1—N1—C1—C2	114.1 (4)	C5—C4—C10—C11	129.9 (4)
N1—C1—C2—C3	67.1 (5)	C3—C4—C10—C11	−104.8 (5)
C6—C1—C2—C3	−51.5 (5)	N3—C10—C11—C12	−0.6 (5)
C1—C2—C3—C4	64.8 (5)	C4—C10—C11—C12	178.9 (4)
C2—C3—C4—C10	−169.0 (3)	C10—C11—C12—C13	0.7 (5)
C2—C3—C4—C5	−42.7 (4)	C11—C12—C13—N3	−0.6 (5)
C10—C4—C5—C6	142.0 (3)	C11—C12—C13—C14	176.3 (4)
C3—C4—C5—C6	15.2 (4)	C10—N3—C13—C12	0.3 (4)
C10—C4—C5—C7	−41.9 (5)	C10—N3—C13—C14	−176.9 (4)
C3—C4—C5—C7	−168.7 (3)	C12—C13—C14—O4	−174.7 (5)
C8—N2—C6—C5	0.4 (3)	N3—C13—C14—O4	1.8 (8)
C8—N2—C6—C1	−176.9 (3)	O2—S1—C15—C16	112.6 (3)
C7—C5—C6—N2	−0.9 (4)	O1—S1—C15—C16	−16.2 (3)
C4—C5—C6—N2	176.0 (3)	N1—S1—C15—C16	−130.5 (3)
C7—C5—C6—C1	176.3 (3)	O2—S1—C15—C20	−63.6 (4)
C4—C5—C6—C1	−6.8 (5)	O1—S1—C15—C20	167.6 (4)
N1—C1—C6—N2	79.7 (4)	N1—S1—C15—C20	53.3 (4)
C2—C1—C6—N2	−159.1 (3)	C20—C15—C16—C17	−0.5 (6)
N1—C1—C6—C5	−97.1 (4)	S1—C15—C16—C17	−176.6 (3)
C2—C1—C6—C5	24.1 (5)	C15—C16—C17—C18	−1.0 (6)
C6—C5—C7—C8	1.1 (4)	C16—C17—C18—C19	0.4 (6)
C4—C5—C7—C8	−175.5 (3)	C16—C17—C18—C21	179.2 (4)
C6—N2—C8—C7	0.3 (3)	C17—C18—C19—C20	1.8 (7)
C6—N2—C8—C9	−178.2 (3)	C21—C18—C19—C20	−177.1 (5)
C5—C7—C8—N2	−0.9 (4)	C16—C15—C20—C19	2.6 (7)
C5—C7—C8—C9	177.5 (3)	S1—C15—C20—C19	178.7 (4)
N2—C8—C9—O3	1.2 (6)	C18—C19—C20—C15	−3.3 (8)
C7—C8—C9—O3	−177.1 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3^i	0.86	2.14	2.966 (4)	161
N2—H2···O1^ii	0.86	2.25	2.934 (4)	137
N3—H3···O3^i	0.86	2.16	2.989 (4)	161

Symmetry codes: (i) x+1/2, −y−1/2, z; (ii) x−1/2, −y−1/2, z.