4-Ethyl-8-methyl-6-phenyl-1-(phenyl­sulfon­yl)-1H,6H-pyrrolo[3,4-f]indole-5,7(1H,6H)-dione

The title mol­ecule, C₂₅H₂₀N₂O₄S, is a rare example of the 1H,6H-pyrrolo[3,4-f]indole ring system, and shows the tricyclic fused ring system to be essentially planar.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.013 Å
• R factor = 0.055
• wR factor = 0.204
• Data-to-parameter ratio = 12.4

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT022_ALERT_3_A Ratio Unique / Expected Reflections too Low ....       0.74
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.79
PLAT081_ALERT_1_A No Maximum Shift/Error Given ...................          ?
PLAT220_ALERT_2_A Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       5.00 Ratio

Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low ....         31 Perc.
PLAT340_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ...         13
PLAT413_ALERT_2_B Short Inter XH3 .. XHn     H17    ..  H18     ..       2.03 Ang.

Alert level C
PLAT030_ALERT_1_C _diffrn_reflns_number .LE.  _reflns_number_total          ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT213_ALERT_2_C Atom C17     has ADP max/min Ratio .............       3.10 prola
PLAT213_ALERT_2_C Atom C18     has ADP max/min Ratio .............       3.20 prola
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.38 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C17
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C18
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C15
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C20
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist.   C15    -C20           1.37 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  O1     ..  C7      ..       3.01 Ang.

Alert level G
REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values
           From the CIF: _diffrn_reflns_theta_max           27.50
           From the CIF: _reflns_number_total               3606
           From the CIF: _diffrn_reflns_limit_ max hkl   21.   16.   22.
           From the CIF: _diffrn_reflns_limit_ min hkl    0.    0.  -23.
           TEST1: Expected hkl limits for theta max
           Calculated maximum hkl   25.   16.   23.
           Calculated minimum hkl  -25.  -16.  -23.

   4 ALERT level A = In general: serious problem
   3 ALERT level B = Potentially serious problem
  11 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  10 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1994); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: CrystalStructure (Rigaku/MSC, 2005); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.

4-Ethyl-8-methyl-6-phenyl-1-(phenylsulfonyl)- 1H,6H-pyrrolo[3,4-f]indole-5,7(1H,6H)-dione

Crystal data

C25H20N2O4S	F(000) = 1856
Mr = 444.49	Dx = 1.397 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -C 2yc	Cell parameters from 20 reflections
a = 19.751 (4) Å	θ = 6.2–7.6°
b = 12.534 (5) Å	µ = 0.19 mm^−1
c = 17.747 (4) Å	T = 296 K
β = 105.820 (17)°	Prism, colorless
V = 4227 (2) Å^3	0.50 × 0.30 × 0.20 mm
Z = 8

Data collection

Rigaku AFC-6S diffractometer	1135 reflections with I > 2σ(I)
Radiation source: normal-focus sealed tube	Rint = 0.000
Graphite monochromator	θmax = 27.5°, θmin = 2.0°
ω/2θ scans	h = 0→21
Absorption correction: ψ scan (North et al., 1968)	k = 0→16
Tmin = 0.911, Tmax = 0.963	l = −23→22
3606 measured reflections	3 standard reflections every 150 reflections
3606 independent reflections	intensity decay: 0.4%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.055	H-atom parameters constrained
wR(F^2) = 0.204	w = 1/[σ^2(Fo^2) + (0.0594P)^2 + 10.5049P] where P = (Fo^2 + 2Fc^2)/3
S = 1.0	(Δ/σ)max = 0.00o
3606 reflections	Δρmax = 0.30 e Å^−3
291 parameters	Δρmin = −0.36 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00068 (18)

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
S1	0.31394 (10)	0.30743 (16)	−0.19920 (10)	0.0481 (6)
O1	0.2797 (3)	0.3966 (4)	−0.1750 (3)	0.0665 (15)
O2	0.2911 (2)	0.2736 (4)	−0.2791 (3)	0.0622 (15)
O3	0.3697 (3)	−0.0264 (4)	0.1946 (3)	0.0598 (14)
O4	0.3982 (3)	0.3335 (4)	0.1716 (3)	0.0605 (15)
N1	0.3035 (3)	0.2006 (4)	−0.1475 (3)	0.0437 (14)
N2	0.3872 (3)	0.1559 (4)	0.2043 (3)	0.0434 (15)
C2	0.2839 (4)	0.1020 (6)	−0.1855 (4)	0.051 (2)
H1	0.2712	0.0923	−0.2395	0.061*
C3	0.2863 (3)	0.0249 (6)	−0.1334 (4)	0.0511 (19)
H2	0.2751	−0.0465	−0.1446	0.061*
C4	0.3092 (3)	0.0711 (5)	−0.0574 (4)	0.0395 (17)
C5	0.3211 (3)	0.0203 (5)	0.0162 (4)	0.0398 (17)
C6	0.3450 (3)	0.0875 (5)	0.0796 (4)	0.0377 (17)
C7	0.3671 (3)	0.0601 (6)	0.1633 (4)	0.0466 (18)
C8	0.3825 (3)	0.2421 (6)	0.1512 (4)	0.0440 (18)
C9	0.3554 (3)	0.1969 (5)	0.0708 (4)	0.0354 (15)
C10	0.3446 (3)	0.2486 (5)	−0.0002 (4)	0.0365 (16)
C11	0.3207 (3)	0.1812 (5)	−0.0648 (3)	0.0343 (16)
C12	0.3083 (4)	−0.0973 (5)	0.0252 (4)	0.053 (2)
H13	0.3105	−0.1343	−0.0221	0.063*
H14	0.3453	−0.1255	0.0683	0.063*
C13	0.2379 (4)	−0.1184 (6)	0.0401 (5)	0.074 (2)
H15	0.2432	−0.1183	0.0955	0.088*
H16	0.2206	−0.1867	0.0188	0.088*
H17	0.2053	−0.0638	0.0157	0.088*
C14	0.3598 (4)	0.3657 (5)	−0.0030 (4)	0.057 (2)
H18	0.3185	0.4059	−0.0027	0.069*
H19	0.3732	0.3814	−0.0499	0.069*
H20	0.3975	0.3848	0.0419	0.069*
C15	0.4045 (4)	0.3278 (6)	−0.1739 (3)	0.0460 (19)
C16	0.4296 (5)	0.4302 (8)	−0.1660 (5)	0.089 (3)
H3	0.3989	0.4877	−0.1710	0.107*
C17	0.5021 (9)	0.4470 (14)	−0.1503 (8)	0.154 (8)
H4	0.5205	0.5157	−0.1433	0.185*
C18	0.5447 (8)	0.362 (2)	−0.1455 (8)	0.171 (11)
H5	0.5930	0.3729	−0.1355	0.206*
C19	0.5192 (6)	0.2623 (15)	−0.1549 (7)	0.133 (6)
H6	0.5501	0.2054	−0.1514	0.160*
C20	0.4483 (4)	0.2425 (8)	−0.1695 (4)	0.070 (2)
H7	0.4308	0.1732	−0.1761	0.083*
C21	0.4122 (3)	0.1657 (6)	0.2869 (4)	0.0461 (19)
C22	0.3935 (4)	0.2515 (7)	0.3258 (5)	0.064 (2)
H8	0.3634	0.3037	0.2980	0.076*
C23	0.4194 (5)	0.2595 (9)	0.4057 (6)	0.092 (3)
H9	0.4071	0.3179	0.4314	0.111*
C24	0.4628 (5)	0.1836 (11)	0.4479 (5)	0.091 (3)
H10	0.4805	0.1910	0.5019	0.110*
C25	0.4805 (4)	0.0960 (9)	0.4108 (5)	0.077 (3)
H11	0.5086	0.0426	0.4399	0.093*
C26	0.4567 (4)	0.0870 (7)	0.3302 (4)	0.060 (2)
H12	0.4701	0.0291	0.3048	0.072*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0477 (13)	0.0509 (12)	0.0464 (12)	0.0075 (10)	0.0141 (9)	0.0048 (10)
O1	0.071 (4)	0.061 (4)	0.073 (4)	0.026 (3)	0.028 (3)	0.009 (3)
O2	0.065 (4)	0.080 (4)	0.035 (3)	−0.001 (3)	0.003 (2)	−0.001 (3)
O3	0.077 (4)	0.042 (3)	0.061 (3)	−0.001 (3)	0.019 (3)	0.014 (3)
O4	0.088 (4)	0.047 (3)	0.041 (3)	−0.015 (3)	0.009 (3)	−0.009 (2)
N1	0.056 (4)	0.041 (4)	0.034 (3)	−0.010 (3)	0.011 (3)	−0.006 (3)
N2	0.047 (4)	0.047 (4)	0.037 (3)	−0.002 (3)	0.013 (3)	0.004 (3)
C2	0.056 (5)	0.058 (5)	0.037 (4)	−0.010 (4)	0.010 (4)	−0.009 (4)
C3	0.057 (5)	0.038 (4)	0.063 (5)	−0.010 (4)	0.026 (4)	−0.019 (4)
C4	0.044 (4)	0.035 (4)	0.043 (4)	−0.008 (3)	0.018 (3)	−0.010 (4)
C5	0.037 (4)	0.031 (4)	0.052 (5)	−0.007 (3)	0.014 (3)	−0.007 (4)
C6	0.029 (4)	0.038 (5)	0.046 (4)	−0.004 (3)	0.010 (3)	0.002 (3)
C7	0.040 (5)	0.049 (5)	0.051 (5)	−0.009 (4)	0.014 (4)	−0.001 (4)
C8	0.046 (5)	0.047 (5)	0.042 (4)	0.000 (4)	0.016 (4)	−0.004 (4)
C9	0.032 (4)	0.031 (4)	0.043 (4)	−0.006 (3)	0.011 (3)	−0.009 (4)
C10	0.034 (4)	0.028 (4)	0.051 (5)	0.004 (3)	0.018 (3)	0.000 (4)
C11	0.028 (4)	0.036 (4)	0.038 (4)	0.002 (3)	0.008 (3)	−0.002 (3)
C12	0.071 (5)	0.020 (4)	0.072 (5)	−0.001 (4)	0.026 (4)	0.001 (4)
C13	0.087 (7)	0.044 (5)	0.098 (6)	−0.016 (5)	0.039 (5)	−0.008 (5)
C14	0.074 (6)	0.043 (5)	0.052 (5)	−0.007 (4)	0.014 (4)	−0.003 (4)
C15	0.051 (5)	0.062 (5)	0.029 (4)	−0.007 (4)	0.018 (3)	−0.004 (4)
C16	0.106 (8)	0.084 (7)	0.096 (7)	−0.044 (6)	0.059 (6)	−0.023 (6)
C17	0.164 (15)	0.203 (17)	0.126 (11)	−0.145 (13)	0.092 (12)	−0.085 (11)
C18	0.079 (11)	0.39 (4)	0.047 (6)	−0.076 (15)	0.027 (7)	−0.041 (13)
C19	0.055 (9)	0.27 (2)	0.071 (8)	0.047 (10)	0.013 (6)	0.054 (10)
C20	0.049 (6)	0.103 (7)	0.060 (5)	0.016 (5)	0.020 (4)	0.021 (5)
C21	0.043 (5)	0.072 (6)	0.024 (4)	−0.010 (4)	0.011 (3)	−0.001 (4)
C22	0.051 (5)	0.085 (6)	0.054 (5)	−0.016 (5)	0.014 (4)	−0.010 (5)
C23	0.076 (7)	0.133 (10)	0.069 (7)	−0.018 (7)	0.021 (6)	−0.032 (6)
C24	0.055 (6)	0.167 (12)	0.053 (6)	−0.021 (7)	0.016 (5)	−0.005 (8)
C25	0.055 (6)	0.126 (9)	0.051 (6)	0.002 (6)	0.016 (5)	0.032 (6)
C26	0.045 (5)	0.087 (6)	0.051 (5)	−0.004 (5)	0.019 (4)	0.023 (5)

Geometric parameters (Å, º)

S1—O2	1.430 (5)	C13—H15	0.9600
S1—O1	1.431 (5)	C13—H16	0.9600
S1—N1	1.668 (5)	C13—H17	0.9600
S1—C15	1.741 (7)	C14—H18	0.9600
O3—C7	1.212 (8)	C14—H19	0.9600
O4—C8	1.216 (7)	C14—H20	0.9600
N1—C2	1.411 (8)	C15—C20	1.364 (10)
N1—C11	1.434 (7)	C15—C16	1.369 (10)
N2—C7	1.404 (8)	C16—C17	1.397 (16)
N2—C21	1.419 (8)	C16—H3	0.9300
N2—C8	1.420 (8)	C17—C18	1.35 (2)
C2—C3	1.329 (9)	C17—H4	0.9300
C2—H1	0.9300	C18—C19	1.34 (2)
C3—C4	1.423 (9)	C18—H5	0.9300
C3—H2	0.9300	C19—C20	1.376 (13)
C4—C11	1.411 (8)	C19—H6	0.9300
C4—C5	1.414 (8)	C20—H7	0.9300
C5—C6	1.382 (8)	C21—C22	1.382 (10)
C5—C12	1.510 (8)	C21—C26	1.403 (9)
C6—C9	1.401 (8)	C22—C23	1.373 (11)
C6—C7	1.470 (9)	C22—H8	0.9300
C8—C9	1.491 (9)	C23—C24	1.361 (13)
C9—C10	1.381 (9)	C23—H9	0.9300
C10—C11	1.397 (9)	C24—C25	1.374 (12)
C10—C14	1.503 (8)	C24—H10	0.9300
C12—C13	1.509 (9)	C25—C26	1.383 (10)
C12—H13	0.9700	C25—H11	0.9300
C12—H14	0.9700	C26—H12	0.9300
O2—S1—O1	118.8 (3)	C12—C13—H15	109.5
O2—S1—N1	104.8 (3)	C12—C13—H16	109.5
O1—S1—N1	108.8 (3)	H15—C13—H16	109.5
O2—S1—C15	108.9 (3)	C12—C13—H17	109.5
O1—S1—C15	110.1 (3)	H15—C13—H17	109.5
N1—S1—C15	104.4 (3)	H16—C13—H17	109.5
C2—N1—C11	107.4 (5)	C10—C14—H18	109.5
C2—N1—S1	119.9 (4)	C10—C14—H19	109.5
C11—N1—S1	132.0 (4)	H18—C14—H19	109.5
C7—N2—C21	125.4 (6)	C10—C14—H20	109.5
C7—N2—C8	110.4 (5)	H18—C14—H20	109.5
C21—N2—C8	124.2 (6)	H19—C14—H20	109.5
C3—C2—N1	110.6 (6)	C20—C15—C16	121.6 (8)
C3—C2—H1	124.7	C20—C15—S1	119.4 (6)
N1—C2—H1	124.7	C16—C15—S1	118.8 (7)
C2—C3—C4	107.7 (6)	C15—C16—C17	118.9 (11)
C2—C3—H2	126.1	C15—C16—H3	120.5
C4—C3—H2	126.1	C17—C16—H3	120.5
C11—C4—C5	122.4 (6)	C18—C17—C16	118.9 (15)
C11—C4—C3	109.2 (6)	C18—C17—H4	120.6
C5—C4—C3	128.5 (6)	C16—C17—H4	120.6
C6—C5—C4	114.3 (6)	C19—C18—C17	121.5 (16)
C6—C5—C12	122.6 (6)	C19—C18—H5	119.3
C4—C5—C12	123.1 (6)	C17—C18—H5	119.3
C5—C6—C9	122.3 (6)	C18—C19—C20	121.3 (15)
C5—C6—C7	128.4 (6)	C18—C19—H6	119.3
C9—C6—C7	109.2 (6)	C20—C19—H6	119.3
O3—C7—N2	123.9 (6)	C15—C20—C19	117.8 (10)
O3—C7—C6	129.4 (7)	C15—C20—H7	121.1
N2—C7—C6	106.7 (6)	C19—C20—H7	121.1
O4—C8—N2	123.6 (6)	C22—C21—C26	119.2 (7)
O4—C8—C9	129.6 (7)	C22—C21—N2	121.2 (7)
N2—C8—C9	106.7 (6)	C26—C21—N2	119.6 (7)
C10—C9—C6	124.7 (6)	C23—C22—C21	119.7 (9)
C10—C9—C8	128.4 (6)	C23—C22—H8	120.1
C6—C9—C8	106.9 (6)	C21—C22—H8	120.1
C9—C10—C11	113.5 (6)	C24—C23—C22	121.3 (10)
C9—C10—C14	120.3 (6)	C24—C23—H9	119.3
C11—C10—C14	126.1 (6)	C22—C23—H9	119.3
C10—C11—C4	122.8 (6)	C23—C24—C25	119.9 (9)
C10—C11—N1	132.0 (6)	C23—C24—H10	120.0
C4—C11—N1	105.1 (5)	C25—C24—H10	120.0
C13—C12—C5	112.2 (6)	C24—C25—C26	120.1 (9)
C13—C12—H13	109.2	C24—C25—H11	119.9
C5—C12—H13	109.2	C26—C25—H11	119.9
C13—C12—H14	109.2	C25—C26—C21	119.6 (8)
C5—C12—H14	109.2	C25—C26—H12	120.2
H13—C12—H14	107.9	C21—C26—H12	120.2