3-(1H-Indol-3-yl)-4-(3,4,5-tri­methoxy­phenyl)-2,5-di­hydro-1H-pyrrole-2,5-dione

The crystal structure of the title compound, C₂₁H₁₈N₂O₅, was determined in order to study the electrocyclic reactivity of 3,4-di­aryl-1H-pyrrole-2,5-dione derivatives. Intermolecular hydrogen bonds form sheets.

Key indicators

• Single-crystal X-ray study
• T = 193 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.044
• wR factor = 0.120
• Data-to-parameter ratio = 13.3

checkCIF/PLATON results

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Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.65 mm

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

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

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Computing details

Data collection: CAD-4 Software (Enraf–Nonius 1989); cell refinement: CAD-4 Software; data reduction: CORINC (Dräger & Gattow, 1971); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELX97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

3-(1H-Indol-3-yl)-4-(3,4,5-trimethoxyphenyl)-2,5-dihydro-1H-pyrrole-2,5-dione

Crystal data

C21H18N2O5	F(000) = 1584
Mr = 378.38	Dx = 1.439 Mg m^−3
Monoclinic, C2/c	Melting point: 227 K
Hall symbol: -C 2yc	Cu Kα radiation, λ = 1.54178 Å
a = 18.448 (2) Å	Cell parameters from 25 reflections
b = 9.9631 (4) Å	θ = 65–73°
c = 20.029 (2) Å	µ = 0.86 mm^−1
β = 108.422 (5)°	T = 193 K
V = 3492.7 (5) Å^3	Block, yellow
Z = 8	0.65 × 0.60 × 0.30 mm

Data collection

Enraf–Nonius CAD-4 diffractometer	3465 reflections with I > 2σ(I)
Radiation source: rotating anode	Rint = 0.061
Graphite monochromator	θmax = 74.3°, θmin = 4.7°
θ/2ω scans	h = 0→22
Absorption correction: ψ scan (CORINC; Dräger & Gattow, 1971)	k = 0→12
Tmin = 0.647, Tmax = 0.772	l = −25→23
3673 measured reflections	3 standard reflections every 60 min
3559 independent reflections	intensity decay: 2%

Refinement

Refinement on F^2	Secondary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.044	Only H-atom displacement parameters refined
wR(F^2) = 0.121	w = 1/[σ^2(Fo^2) + (0.0612P)^2 + 3.5777P] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max < 0.001
3559 reflections	Δρmax = 0.30 e Å^−3
268 parameters	Δρmin = −0.26 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: 0.00211 (15)

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
C1	0.24772 (8)	0.70308 (14)	0.60885 (8)	0.0239 (3)
C1A	0.26870 (8)	0.58410 (14)	0.65221 (7)	0.0229 (3)
C2	0.23617 (8)	0.51244 (15)	0.69591 (8)	0.0266 (3)
H2	0.1867	0.5403	0.7031	0.028 (4)*
C3	0.27376 (9)	0.40110 (17)	0.73143 (9)	0.0324 (4)
H3	0.2524	0.3498	0.7591	0.034 (5)*
C4	0.34340 (10)	0.35838 (17)	0.72429 (9)	0.0360 (4)
H4	0.3695	0.2810	0.7492	0.046 (6)*
C5	0.37785 (9)	0.42792 (17)	0.68304 (9)	0.0338 (4)
H5	0.4273	0.4011	0.6788	0.043 (5)*
C5A	0.34010 (8)	0.54181 (16)	0.64791 (8)	0.0274 (3)
N6	0.36221 (7)	0.63182 (15)	0.60584 (7)	0.0334 (3)
H6	0.4113 (14)	0.63433 (16)	0.5993 (2)	0.064 (7)*
C7	0.30839 (9)	0.72855 (16)	0.58421 (9)	0.0301 (3)
H7	0.3123	0.8018	0.5512	0.036 (5)*
C8	0.17844 (8)	0.78251 (14)	0.59173 (7)	0.0233 (3)
C9	0.17999 (9)	0.93101 (15)	0.57740 (8)	0.0290 (3)
N10	0.10805 (8)	0.97919 (13)	0.57035 (8)	0.0323 (3)
H10	0.0924 (5)	1.063 (3)	0.5628 (3)	0.066 (7)*
C11	0.06015 (8)	0.87765 (14)	0.57834 (8)	0.0267 (3)
C12	0.10536 (8)	0.75039 (14)	0.58747 (7)	0.0222 (3)
C13	0.07293 (8)	0.61631 (13)	0.58932 (7)	0.0212 (3)
C14	0.10187 (8)	0.51106 (14)	0.55963 (7)	0.0215 (3)
H14	0.1400	0.5302	0.5386	0.027 (4)*
C15	0.08201 (8)	0.37977 (13)	0.56904 (7)	0.0208 (3)
C16	0.03143 (8)	0.35378 (14)	0.60651 (7)	0.0217 (3)
C17	−0.00263 (8)	0.45997 (14)	0.63094 (7)	0.0227 (3)
C18	0.01819 (8)	0.59217 (14)	0.62294 (7)	0.0225 (3)
H18	−0.0034	0.6684	0.6424	0.029 (4)*
O19	0.23359 (7)	0.99622 (12)	0.57272 (8)	0.0418 (3)
O20	−0.00483 (6)	0.89340 (11)	0.57882 (7)	0.0351 (3)
O21	0.11078 (6)	0.26923 (10)	0.54648 (6)	0.0280 (3)
C22	0.16660 (10)	0.29094 (17)	0.51232 (10)	0.0382 (4)
H22A	0.1465	0.3460	0.4699	0.044 (3)*
H22B	0.1794	0.2065	0.4991	0.044 (3)*
H22C	0.2079	0.3312	0.5409	0.044 (3)*
O23	0.01538 (6)	0.22208 (10)	0.61819 (6)	0.0267 (3)
C24	0.06103 (11)	0.17653 (17)	0.68671 (9)	0.0386 (4)
H24A	0.1159	0.1754	0.6910	0.050 (4)*
H24B	0.0430	0.0884	0.6913	0.050 (4)*
H24C	0.0598	0.2351	0.7247	0.050 (4)*
O25	−0.05360 (6)	0.42214 (11)	0.66402 (7)	0.0346 (3)
C26	−0.09675 (9)	0.52412 (17)	0.68398 (9)	0.0326 (4)
H26A	−0.1276	0.5737	0.6417	0.044 (3)*
H26B	−0.0627	0.5817	0.7203	0.044 (3)*
H26C	−0.1330	0.4769	0.7028	0.044 (3)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0209 (7)	0.0233 (7)	0.0278 (7)	−0.0045 (5)	0.0080 (5)	0.0007 (5)
C1A	0.0197 (6)	0.0235 (7)	0.0252 (7)	−0.0004 (5)	0.0068 (5)	−0.0014 (5)
C2	0.0237 (7)	0.0285 (7)	0.0291 (7)	0.0013 (6)	0.0105 (6)	0.0027 (6)
C3	0.0326 (8)	0.0315 (8)	0.0338 (8)	0.0017 (6)	0.0114 (6)	0.0081 (6)
C4	0.0350 (9)	0.0297 (8)	0.0411 (9)	0.0106 (7)	0.0087 (7)	0.0055 (7)
C5	0.0255 (7)	0.0355 (8)	0.0408 (9)	0.0085 (6)	0.0108 (6)	−0.0015 (7)
C5A	0.0216 (7)	0.0314 (8)	0.0302 (7)	−0.0010 (6)	0.0096 (6)	−0.0019 (6)
N6	0.0209 (6)	0.0420 (8)	0.0408 (8)	−0.0019 (5)	0.0147 (5)	0.0046 (6)
C7	0.0243 (7)	0.0324 (8)	0.0342 (8)	−0.0062 (6)	0.0100 (6)	0.0045 (6)
C8	0.0242 (7)	0.0192 (7)	0.0263 (7)	−0.0033 (5)	0.0077 (5)	0.0010 (5)
C9	0.0272 (7)	0.0205 (7)	0.0363 (8)	−0.0043 (6)	0.0057 (6)	0.0028 (6)
N10	0.0295 (7)	0.0170 (6)	0.0489 (8)	−0.0009 (5)	0.0101 (6)	0.0058 (5)
C11	0.0265 (7)	0.0198 (7)	0.0326 (7)	−0.0013 (5)	0.0075 (6)	0.0008 (6)
C12	0.0232 (7)	0.0170 (6)	0.0265 (7)	−0.0014 (5)	0.0081 (5)	0.0003 (5)
C13	0.0192 (6)	0.0177 (6)	0.0261 (7)	−0.0012 (5)	0.0064 (5)	0.0019 (5)
C14	0.0193 (6)	0.0211 (7)	0.0258 (7)	−0.0027 (5)	0.0096 (5)	0.0013 (5)
C15	0.0194 (6)	0.0184 (6)	0.0257 (7)	−0.0001 (5)	0.0086 (5)	−0.0011 (5)
C16	0.0200 (6)	0.0173 (6)	0.0288 (7)	−0.0039 (5)	0.0092 (5)	0.0010 (5)
C17	0.0186 (6)	0.0228 (7)	0.0292 (7)	−0.0026 (5)	0.0112 (5)	−0.0005 (5)
C18	0.0200 (6)	0.0202 (7)	0.0287 (7)	−0.0008 (5)	0.0096 (5)	−0.0020 (5)
O19	0.0299 (6)	0.0268 (6)	0.0658 (8)	−0.0086 (5)	0.0111 (6)	0.0110 (6)
O20	0.0259 (6)	0.0250 (5)	0.0546 (7)	0.0023 (4)	0.0132 (5)	0.0018 (5)
O21	0.0311 (6)	0.0186 (5)	0.0425 (6)	−0.0001 (4)	0.0233 (5)	−0.0020 (4)
C22	0.0441 (10)	0.0278 (8)	0.0573 (11)	0.0037 (7)	0.0370 (9)	0.0028 (7)
O23	0.0263 (5)	0.0178 (5)	0.0395 (6)	−0.0038 (4)	0.0154 (4)	0.0027 (4)
C24	0.0495 (10)	0.0274 (8)	0.0401 (9)	0.0005 (7)	0.0161 (8)	0.0084 (7)
O25	0.0343 (6)	0.0265 (6)	0.0555 (7)	−0.0034 (5)	0.0320 (6)	−0.0019 (5)
C26	0.0253 (7)	0.0379 (9)	0.0400 (8)	0.0018 (6)	0.0180 (6)	−0.0040 (7)

Geometric parameters (Å, º)

C1—C7	1.382 (2)	C12—C13	1.4690 (18)
C1—C1A	1.448 (2)	C13—C14	1.3925 (19)
C1—C8	1.449 (2)	C13—C18	1.4001 (19)
C1A—C2	1.403 (2)	C14—C15	1.3872 (19)
C1A—C5A	1.4111 (19)	C14—H14	0.9467
C2—C3	1.380 (2)	C15—O21	1.3603 (16)
C2—H2	1.0062	C15—C16	1.3941 (19)
C3—C4	1.403 (2)	C16—O23	1.3811 (16)
C3—H3	0.9275	C16—C17	1.396 (2)
C4—C5	1.378 (3)	C17—O25	1.3634 (16)
C4—H4	0.9609	C17—C18	1.3954 (19)
C5—C5A	1.399 (2)	C18—H18	0.9926
C5—H5	0.9800	O21—C22	1.4215 (18)
C5A—N6	1.378 (2)	C22—H22A	0.9801
N6—C7	1.353 (2)	C22—H22B	0.9349
N6—H6	0.9560	C22—H22C	0.8911
C7—H7	1.0027	O23—C24	1.438 (2)
C8—C12	1.362 (2)	C24—H24A	0.9890
C8—C9	1.5091 (19)	C24—H24B	0.9533
C9—O19	1.2112 (19)	C24—H24C	0.9646
C9—N10	1.376 (2)	O25—C26	1.4237 (18)
N10—C11	1.3854 (19)	C26—H26A	0.9897
N10—H10	0.8767	C26—H26B	0.9821
C11—O20	1.2120 (19)	C26—H26C	0.9859
C11—C12	1.4968 (19)
C7—C1—C1A	105.74 (13)	C13—C12—C11	123.89 (12)
C7—C1—C8	124.65 (14)	C14—C13—C18	120.54 (12)
C1A—C1—C8	129.60 (12)	C14—C13—C12	117.38 (12)
C2—C1A—C5A	118.53 (13)	C18—C13—C12	121.99 (12)
C2—C1A—C1	134.82 (13)	C15—C14—C13	119.91 (12)
C5A—C1A—C1	106.59 (12)	C15—C14—H14	121.0
C3—C2—C1A	119.09 (14)	C13—C14—H14	118.5
C3—C2—H2	118.6	O21—C15—C14	124.80 (12)
C1A—C2—H2	122.3	O21—C15—C16	115.23 (12)
C2—C3—C4	121.22 (15)	C14—C15—C16	119.92 (12)
C2—C3—H3	120.8	O23—C16—C15	118.91 (12)
C4—C3—H3	118.0	O23—C16—C17	121.09 (12)
C5—C4—C3	121.29 (15)	C15—C16—C17	120.00 (12)
C5—C4—H4	117.7	O25—C17—C18	125.02 (13)
C3—C4—H4	121.0	O25—C17—C16	114.63 (12)
C4—C5—C5A	117.30 (14)	C18—C17—C16	120.30 (12)
C4—C5—H5	122.3	C17—C18—C13	118.94 (12)
C5A—C5—H5	120.4	C17—C18—H18	121.2
N6—C5A—C5	129.71 (14)	C13—C18—H18	119.8
N6—C5A—C1A	107.79 (13)	C15—O21—C22	117.05 (11)
C5—C5A—C1A	122.50 (14)	O21—C22—H22A	111.7
C7—N6—C5A	109.29 (13)	O21—C22—H22B	106.6
C7—N6—H6	124.7	H22A—C22—H22B	108.6
C5A—N6—H6	125.3	O21—C22—H22C	111.2
N6—C7—C1	110.50 (14)	H22A—C22—H22C	108.5
N6—C7—H7	122.1	H22B—C22—H22C	110.2
C1—C7—H7	127.2	C16—O23—C24	111.67 (12)
C12—C8—C1	131.92 (13)	O23—C24—H24A	111.2
C12—C8—C9	107.25 (12)	O23—C24—H24B	105.4
C1—C8—C9	120.79 (12)	H24A—C24—H24B	111.1
O19—C9—N10	126.12 (14)	O23—C24—H24C	114.1
O19—C9—C8	127.27 (14)	H24A—C24—H24C	102.5
N10—C9—C8	106.61 (12)	H24B—C24—H24C	112.7
C9—N10—C11	111.29 (13)	C17—O25—C26	118.15 (12)
C9—N10—H10	127.1	O25—C26—H26A	109.8
C11—N10—H10	121.6	O25—C26—H26B	110.0
O20—C11—N10	125.09 (14)	H26A—C26—H26B	113.7
O20—C11—C12	128.55 (13)	O25—C26—H26C	105.9
N10—C11—C12	106.35 (12)	H26A—C26—H26C	106.8
C8—C12—C13	127.97 (13)	H26B—C26—H26C	110.3
C8—C12—C11	108.12 (12)
C7—C1—C1A—C2	174.37 (17)	C9—C8—C12—C13	172.42 (14)
C8—C1—C1A—C2	−6.5 (3)	C1—C8—C12—C11	171.49 (15)
C7—C1—C1A—C5A	−2.77 (16)	C9—C8—C12—C11	−6.09 (16)
C8—C1—C1A—C5A	176.37 (14)	O20—C11—C12—C8	−172.70 (16)
C5A—C1A—C2—C3	−1.9 (2)	N10—C11—C12—C8	6.05 (17)
C1—C1A—C2—C3	−178.81 (16)	O20—C11—C12—C13	8.7 (3)
C1A—C2—C3—C4	−0.3 (2)	N10—C11—C12—C13	−172.53 (13)
C2—C3—C4—C5	1.7 (3)	C8—C12—C13—C14	−33.3 (2)
C3—C4—C5—C5A	−0.8 (3)	C11—C12—C13—C14	144.94 (14)
C4—C5—C5A—N6	177.41 (16)	C8—C12—C13—C18	143.07 (15)
C4—C5—C5A—C1A	−1.5 (2)	C11—C12—C13—C18	−38.6 (2)
C2—C1A—C5A—N6	−176.24 (13)	C18—C13—C14—C15	−6.1 (2)
C1—C1A—C5A—N6	1.45 (16)	C12—C13—C14—C15	170.33 (13)
C2—C1A—C5A—C5	2.9 (2)	C13—C14—C15—O21	−175.41 (13)
C1—C1A—C5A—C5	−179.39 (14)	C13—C14—C15—C16	1.8 (2)
C5—C5A—N6—C7	−178.61 (17)	O21—C15—C16—O23	0.62 (19)
C1A—C5A—N6—C7	0.47 (18)	C14—C15—C16—O23	−176.85 (12)
C5A—N6—C7—C1	−2.34 (19)	O21—C15—C16—C17	−178.77 (12)
C1A—C1—C7—N6	3.16 (18)	C14—C15—C16—C17	3.8 (2)
C8—C1—C7—N6	−176.03 (14)	O23—C16—C17—O25	−2.2 (2)
C7—C1—C8—C12	151.61 (17)	C15—C16—C17—O25	177.15 (13)
C1A—C1—C8—C12	−27.4 (3)	O23—C16—C17—C18	175.56 (13)
C7—C1—C8—C9	−31.1 (2)	C15—C16—C17—C18	−5.1 (2)
C1A—C1—C8—C9	149.92 (15)	O25—C17—C18—C13	178.32 (14)
C12—C8—C9—O19	−175.73 (17)	C16—C17—C18—C13	0.8 (2)
C1—C8—C9—O19	6.4 (3)	C14—C13—C18—C17	4.8 (2)
C12—C8—C9—N10	4.12 (17)	C12—C13—C18—C17	−171.49 (13)
C1—C8—C9—N10	−173.79 (13)	C14—C15—O21—C22	1.6 (2)
O19—C9—N10—C11	179.63 (17)	C16—C15—O21—C22	−175.76 (14)
C8—C9—N10—C11	−0.21 (18)	C15—C16—O23—C24	97.35 (16)
C9—N10—C11—O20	175.40 (15)	C17—C16—O23—C24	−83.26 (17)
C9—N10—C11—C12	−3.40 (18)	C18—C17—O25—C26	8.8 (2)
C1—C8—C12—C13	−10.0 (3)	C16—C17—O25—C26	−173.55 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6···O23^i	0.96	2.03	2.9005 (17)	150
N10—H10···O21^ii	0.88	2.13	2.9320 (17)	152
N10—H10···O23^ii	0.88	2.60	3.2759 (18)	134

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