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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805004605/bt6600sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805004605/bt6600Isup2.hkl
Contains datablock I

CCDC reference: 269374

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

No syntax errors found



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

Computing details top

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 top
Crystal data top
C21H18N2O5F(000) = 1584
Mr = 378.38Dx = 1.439 Mg m3
Monoclinic, C2/cMelting point: 227 K
Hall symbol: -C 2ycCu Kα radiation, λ = 1.54178 Å
a = 18.448 (2) ÅCell parameters from 25 reflections
b = 9.9631 (4) Åθ = 65–73°
c = 20.029 (2) ŵ = 0.86 mm1
β = 108.422 (5)°T = 193 K
V = 3492.7 (5) Å3Block, yellow
Z = 80.65 × 0.60 × 0.30 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer
3465 reflections with I > 2σ(I)
Radiation source: rotating anodeRint = 0.061
Graphite monochromatorθmax = 74.3°, θmin = 4.7°
θ/2ω scansh = 022
Absorption correction: ψ scan
(CORINC; Dräger & Gattow, 1971)
k = 012
Tmin = 0.647, Tmax = 0.772l = 2523
3673 measured reflections3 standard reflections every 60 min
3559 independent reflections intensity decay: 2%
Refinement top
Refinement on F2Secondary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Only H-atom displacement parameters refined
wR(F2) = 0.121 w = 1/[σ2(Fo2) + (0.0612P)2 + 3.5777P]
where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max < 0.001
3559 reflectionsΔρmax = 0.30 e Å3
268 parametersΔρmin = 0.26 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.00211 (15)
Special details top

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 (Å2) top
xyzUiso*/Ueq
C10.24772 (8)0.70308 (14)0.60885 (8)0.0239 (3)
C1A0.26870 (8)0.58410 (14)0.65221 (7)0.0229 (3)
C20.23617 (8)0.51244 (15)0.69591 (8)0.0266 (3)
H20.18670.54030.70310.028 (4)*
C30.27376 (9)0.40110 (17)0.73143 (9)0.0324 (4)
H30.25240.34980.75910.034 (5)*
C40.34340 (10)0.35838 (17)0.72429 (9)0.0360 (4)
H40.36950.28100.74920.046 (6)*
C50.37785 (9)0.42792 (17)0.68304 (9)0.0338 (4)
H50.42730.40110.67880.043 (5)*
C5A0.34010 (8)0.54181 (16)0.64791 (8)0.0274 (3)
N60.36221 (7)0.63182 (15)0.60584 (7)0.0334 (3)
H60.4113 (14)0.63433 (16)0.5993 (2)0.064 (7)*
C70.30839 (9)0.72855 (16)0.58421 (9)0.0301 (3)
H70.31230.80180.55120.036 (5)*
C80.17844 (8)0.78251 (14)0.59173 (7)0.0233 (3)
C90.17999 (9)0.93101 (15)0.57740 (8)0.0290 (3)
N100.10805 (8)0.97919 (13)0.57035 (8)0.0323 (3)
H100.0924 (5)1.063 (3)0.5628 (3)0.066 (7)*
C110.06015 (8)0.87765 (14)0.57834 (8)0.0267 (3)
C120.10536 (8)0.75039 (14)0.58747 (7)0.0222 (3)
C130.07293 (8)0.61631 (13)0.58932 (7)0.0212 (3)
C140.10187 (8)0.51106 (14)0.55963 (7)0.0215 (3)
H140.14000.53020.53860.027 (4)*
C150.08201 (8)0.37977 (13)0.56904 (7)0.0208 (3)
C160.03143 (8)0.35378 (14)0.60651 (7)0.0217 (3)
C170.00263 (8)0.45997 (14)0.63094 (7)0.0227 (3)
C180.01819 (8)0.59217 (14)0.62294 (7)0.0225 (3)
H180.00340.66840.64240.029 (4)*
O190.23359 (7)0.99622 (12)0.57272 (8)0.0418 (3)
O200.00483 (6)0.89340 (11)0.57882 (7)0.0351 (3)
O210.11078 (6)0.26923 (10)0.54648 (6)0.0280 (3)
C220.16660 (10)0.29094 (17)0.51232 (10)0.0382 (4)
H22A0.14650.34600.46990.044 (3)*
H22B0.17940.20650.49910.044 (3)*
H22C0.20790.33120.54090.044 (3)*
O230.01538 (6)0.22208 (10)0.61819 (6)0.0267 (3)
C240.06103 (11)0.17653 (17)0.68671 (9)0.0386 (4)
H24A0.11590.17540.69100.050 (4)*
H24B0.04300.08840.69130.050 (4)*
H24C0.05980.23510.72470.050 (4)*
O250.05360 (6)0.42214 (11)0.66402 (7)0.0346 (3)
C260.09675 (9)0.52412 (17)0.68398 (9)0.0326 (4)
H26A0.12760.57370.64170.044 (3)*
H26B0.06270.58170.72030.044 (3)*
H26C0.13300.47690.70280.044 (3)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0209 (7)0.0233 (7)0.0278 (7)0.0045 (5)0.0080 (5)0.0007 (5)
C1A0.0197 (6)0.0235 (7)0.0252 (7)0.0004 (5)0.0068 (5)0.0014 (5)
C20.0237 (7)0.0285 (7)0.0291 (7)0.0013 (6)0.0105 (6)0.0027 (6)
C30.0326 (8)0.0315 (8)0.0338 (8)0.0017 (6)0.0114 (6)0.0081 (6)
C40.0350 (9)0.0297 (8)0.0411 (9)0.0106 (7)0.0087 (7)0.0055 (7)
C50.0255 (7)0.0355 (8)0.0408 (9)0.0085 (6)0.0108 (6)0.0015 (7)
C5A0.0216 (7)0.0314 (8)0.0302 (7)0.0010 (6)0.0096 (6)0.0019 (6)
N60.0209 (6)0.0420 (8)0.0408 (8)0.0019 (5)0.0147 (5)0.0046 (6)
C70.0243 (7)0.0324 (8)0.0342 (8)0.0062 (6)0.0100 (6)0.0045 (6)
C80.0242 (7)0.0192 (7)0.0263 (7)0.0033 (5)0.0077 (5)0.0010 (5)
C90.0272 (7)0.0205 (7)0.0363 (8)0.0043 (6)0.0057 (6)0.0028 (6)
N100.0295 (7)0.0170 (6)0.0489 (8)0.0009 (5)0.0101 (6)0.0058 (5)
C110.0265 (7)0.0198 (7)0.0326 (7)0.0013 (5)0.0075 (6)0.0008 (6)
C120.0232 (7)0.0170 (6)0.0265 (7)0.0014 (5)0.0081 (5)0.0003 (5)
C130.0192 (6)0.0177 (6)0.0261 (7)0.0012 (5)0.0064 (5)0.0019 (5)
C140.0193 (6)0.0211 (7)0.0258 (7)0.0027 (5)0.0096 (5)0.0013 (5)
C150.0194 (6)0.0184 (6)0.0257 (7)0.0001 (5)0.0086 (5)0.0011 (5)
C160.0200 (6)0.0173 (6)0.0288 (7)0.0039 (5)0.0092 (5)0.0010 (5)
C170.0186 (6)0.0228 (7)0.0292 (7)0.0026 (5)0.0112 (5)0.0005 (5)
C180.0200 (6)0.0202 (7)0.0287 (7)0.0008 (5)0.0096 (5)0.0020 (5)
O190.0299 (6)0.0268 (6)0.0658 (8)0.0086 (5)0.0111 (6)0.0110 (6)
O200.0259 (6)0.0250 (5)0.0546 (7)0.0023 (4)0.0132 (5)0.0018 (5)
O210.0311 (6)0.0186 (5)0.0425 (6)0.0001 (4)0.0233 (5)0.0020 (4)
C220.0441 (10)0.0278 (8)0.0573 (11)0.0037 (7)0.0370 (9)0.0028 (7)
O230.0263 (5)0.0178 (5)0.0395 (6)0.0038 (4)0.0154 (4)0.0027 (4)
C240.0495 (10)0.0274 (8)0.0401 (9)0.0005 (7)0.0161 (8)0.0084 (7)
O250.0343 (6)0.0265 (6)0.0555 (7)0.0034 (5)0.0320 (6)0.0019 (5)
C260.0253 (7)0.0379 (9)0.0400 (8)0.0018 (6)0.0180 (6)0.0040 (7)
Geometric parameters (Å, º) top
C1—C71.382 (2)C12—C131.4690 (18)
C1—C1A1.448 (2)C13—C141.3925 (19)
C1—C81.449 (2)C13—C181.4001 (19)
C1A—C21.403 (2)C14—C151.3872 (19)
C1A—C5A1.4111 (19)C14—H140.9467
C2—C31.380 (2)C15—O211.3603 (16)
C2—H21.0062C15—C161.3941 (19)
C3—C41.403 (2)C16—O231.3811 (16)
C3—H30.9275C16—C171.396 (2)
C4—C51.378 (3)C17—O251.3634 (16)
C4—H40.9609C17—C181.3954 (19)
C5—C5A1.399 (2)C18—H180.9926
C5—H50.9800O21—C221.4215 (18)
C5A—N61.378 (2)C22—H22A0.9801
N6—C71.353 (2)C22—H22B0.9349
N6—H60.9560C22—H22C0.8911
C7—H71.0027O23—C241.438 (2)
C8—C121.362 (2)C24—H24A0.9890
C8—C91.5091 (19)C24—H24B0.9533
C9—O191.2112 (19)C24—H24C0.9646
C9—N101.376 (2)O25—C261.4237 (18)
N10—C111.3854 (19)C26—H26A0.9897
N10—H100.8767C26—H26B0.9821
C11—O201.2120 (19)C26—H26C0.9859
C11—C121.4968 (19)
C7—C1—C1A105.74 (13)C13—C12—C11123.89 (12)
C7—C1—C8124.65 (14)C14—C13—C18120.54 (12)
C1A—C1—C8129.60 (12)C14—C13—C12117.38 (12)
C2—C1A—C5A118.53 (13)C18—C13—C12121.99 (12)
C2—C1A—C1134.82 (13)C15—C14—C13119.91 (12)
C5A—C1A—C1106.59 (12)C15—C14—H14121.0
C3—C2—C1A119.09 (14)C13—C14—H14118.5
C3—C2—H2118.6O21—C15—C14124.80 (12)
C1A—C2—H2122.3O21—C15—C16115.23 (12)
C2—C3—C4121.22 (15)C14—C15—C16119.92 (12)
C2—C3—H3120.8O23—C16—C15118.91 (12)
C4—C3—H3118.0O23—C16—C17121.09 (12)
C5—C4—C3121.29 (15)C15—C16—C17120.00 (12)
C5—C4—H4117.7O25—C17—C18125.02 (13)
C3—C4—H4121.0O25—C17—C16114.63 (12)
C4—C5—C5A117.30 (14)C18—C17—C16120.30 (12)
C4—C5—H5122.3C17—C18—C13118.94 (12)
C5A—C5—H5120.4C17—C18—H18121.2
N6—C5A—C5129.71 (14)C13—C18—H18119.8
N6—C5A—C1A107.79 (13)C15—O21—C22117.05 (11)
C5—C5A—C1A122.50 (14)O21—C22—H22A111.7
C7—N6—C5A109.29 (13)O21—C22—H22B106.6
C7—N6—H6124.7H22A—C22—H22B108.6
C5A—N6—H6125.3O21—C22—H22C111.2
N6—C7—C1110.50 (14)H22A—C22—H22C108.5
N6—C7—H7122.1H22B—C22—H22C110.2
C1—C7—H7127.2C16—O23—C24111.67 (12)
C12—C8—C1131.92 (13)O23—C24—H24A111.2
C12—C8—C9107.25 (12)O23—C24—H24B105.4
C1—C8—C9120.79 (12)H24A—C24—H24B111.1
O19—C9—N10126.12 (14)O23—C24—H24C114.1
O19—C9—C8127.27 (14)H24A—C24—H24C102.5
N10—C9—C8106.61 (12)H24B—C24—H24C112.7
C9—N10—C11111.29 (13)C17—O25—C26118.15 (12)
C9—N10—H10127.1O25—C26—H26A109.8
C11—N10—H10121.6O25—C26—H26B110.0
O20—C11—N10125.09 (14)H26A—C26—H26B113.7
O20—C11—C12128.55 (13)O25—C26—H26C105.9
N10—C11—C12106.35 (12)H26A—C26—H26C106.8
C8—C12—C13127.97 (13)H26B—C26—H26C110.3
C8—C12—C11108.12 (12)
C7—C1—C1A—C2174.37 (17)C9—C8—C12—C13172.42 (14)
C8—C1—C1A—C26.5 (3)C1—C8—C12—C11171.49 (15)
C7—C1—C1A—C5A2.77 (16)C9—C8—C12—C116.09 (16)
C8—C1—C1A—C5A176.37 (14)O20—C11—C12—C8172.70 (16)
C5A—C1A—C2—C31.9 (2)N10—C11—C12—C86.05 (17)
C1—C1A—C2—C3178.81 (16)O20—C11—C12—C138.7 (3)
C1A—C2—C3—C40.3 (2)N10—C11—C12—C13172.53 (13)
C2—C3—C4—C51.7 (3)C8—C12—C13—C1433.3 (2)
C3—C4—C5—C5A0.8 (3)C11—C12—C13—C14144.94 (14)
C4—C5—C5A—N6177.41 (16)C8—C12—C13—C18143.07 (15)
C4—C5—C5A—C1A1.5 (2)C11—C12—C13—C1838.6 (2)
C2—C1A—C5A—N6176.24 (13)C18—C13—C14—C156.1 (2)
C1—C1A—C5A—N61.45 (16)C12—C13—C14—C15170.33 (13)
C2—C1A—C5A—C52.9 (2)C13—C14—C15—O21175.41 (13)
C1—C1A—C5A—C5179.39 (14)C13—C14—C15—C161.8 (2)
C5—C5A—N6—C7178.61 (17)O21—C15—C16—O230.62 (19)
C1A—C5A—N6—C70.47 (18)C14—C15—C16—O23176.85 (12)
C5A—N6—C7—C12.34 (19)O21—C15—C16—C17178.77 (12)
C1A—C1—C7—N63.16 (18)C14—C15—C16—C173.8 (2)
C8—C1—C7—N6176.03 (14)O23—C16—C17—O252.2 (2)
C7—C1—C8—C12151.61 (17)C15—C16—C17—O25177.15 (13)
C1A—C1—C8—C1227.4 (3)O23—C16—C17—C18175.56 (13)
C7—C1—C8—C931.1 (2)C15—C16—C17—C185.1 (2)
C1A—C1—C8—C9149.92 (15)O25—C17—C18—C13178.32 (14)
C12—C8—C9—O19175.73 (17)C16—C17—C18—C130.8 (2)
C1—C8—C9—O196.4 (3)C14—C13—C18—C174.8 (2)
C12—C8—C9—N104.12 (17)C12—C13—C18—C17171.49 (13)
C1—C8—C9—N10173.79 (13)C14—C15—O21—C221.6 (2)
O19—C9—N10—C11179.63 (17)C16—C15—O21—C22175.76 (14)
C8—C9—N10—C110.21 (18)C15—C16—O23—C2497.35 (16)
C9—N10—C11—O20175.40 (15)C17—C16—O23—C2483.26 (17)
C9—N10—C11—C123.40 (18)C18—C17—O25—C268.8 (2)
C1—C8—C12—C1310.0 (3)C16—C17—O25—C26173.55 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N6—H6···O23i0.962.032.9005 (17)150
N10—H10···O21ii0.882.132.9320 (17)152
N10—H10···O23ii0.882.603.2759 (18)134
Symmetry codes: (i) x+1/2, y+1/2, z; (ii) x, y+1, z.
 

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