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The pyrrolidine ring of the title compound, C26H19N3O5, adopts an envelope conformation. The molecular structure is stabilized by C—H...O interactions and the packing of the mol­ecules is stabilized by an N—H...O hydrogen bond and C—H...O intermolecular interactions. A dimer is formed between symmetry-related mol­ecules through N—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803026345/bt6378sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803026345/bt6378Isup2.hkl
Contains datablock I

CCDC reference: 227920

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.052
  • wR factor = 0.163
  • Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.91
Alert level C REFLT03_ALERT_3_C Reflection count < 95% complete From the CIF: _diffrn_reflns_theta_max 27.98 From the CIF: _diffrn_reflns_theta_full 0.00 From the CIF: _reflns_number_total 4747 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 5218 Completeness (_total/calc) 90.97% PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 2.77 Ratio PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... N21 PLAT432_ALERT_2_C Short Inter X...Y Contact C8 .. C8 = 3.18 Ang. PLAT482_ALERT_4_C Small D-H..A Angle Rep for C19 .. O23 = 98.00 Deg. PLAT482_ALERT_4_C Small D-H..A Angle Rep for C24 .. O22 = 98.00 Deg.
1 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: 'ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 1990)'; software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

1-Methyl-4'-(3-nitrophenyl)-1H-indole-3-spiro-2'-pyrrolidine-3'- spiro-2''-indan-2,1'',3''-trione top
Crystal data top
C26H19N3O5Z = 2
Mr = 453.44F(000) = 472
Triclinic, P1Dx = 1.392 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.7610 (6) ÅCell parameters from 2386 reflections
b = 11.6696 (10) Åθ = 2.4–27.2°
c = 11.9952 (9) ŵ = 0.10 mm1
α = 93.392 (2)°T = 293 K
β = 91.092 (1)°Needles, yellow
γ = 93.660 (1)°0.21 × 0.16 × 0.14 mm
V = 1081.98 (15) Å3
Data collection top
CCD Area Detector
diffractometer
4747 independent reflections
Radiation source: fine-focus sealed tube3472 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.014
ω scansθmax = 28.0°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)
h = 1010
Tmin = 0.980, Tmax = 0.986k = 1314
6822 measured reflectionsl = 1015
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.163H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0932P)2 + 0.165P]
where P = (Fo2 + 2Fc2)/3
4747 reflections(Δ/σ)max < 0.000
307 parametersΔρmax = 0.31 e Å3
0 restraintsΔρmin = 0.26 e Å3
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
N10.0636 (2)0.02827 (15)0.14814 (14)0.0613 (5)
H10.01600.01610.11420.074*
C20.1514 (3)0.11612 (18)0.10045 (17)0.0560 (5)
O30.1462 (2)0.13715 (14)0.00201 (12)0.0722 (5)
C40.2656 (2)0.18439 (16)0.19517 (14)0.0465 (4)
C50.2429 (2)0.10601 (15)0.28967 (15)0.0454 (4)
C60.3245 (2)0.10738 (16)0.39291 (17)0.0527 (5)
H60.41080.16400.41370.063*
C70.2763 (3)0.02350 (18)0.46520 (18)0.0605 (5)
H70.33030.02390.53510.073*
C80.1484 (3)0.06093 (18)0.4342 (2)0.0644 (6)
H80.11610.11570.48440.077*
C90.0678 (3)0.06564 (17)0.33022 (19)0.0620 (5)
H90.01700.12320.30910.074*
C100.1176 (2)0.01804 (16)0.25889 (16)0.0506 (4)
C110.2000 (2)0.30860 (15)0.21580 (14)0.0435 (4)
C120.2879 (2)0.37348 (17)0.12103 (15)0.0498 (4)
H120.21270.35810.05460.060*
C130.4519 (3)0.31045 (19)0.09801 (19)0.0652 (6)
H13A0.45590.28520.01970.078*
H13B0.55380.36070.11730.078*
N140.44401 (19)0.21205 (13)0.16730 (13)0.0500 (4)
C150.5400 (3)0.1160 (2)0.1256 (2)0.0767 (7)
H15A0.52820.05500.17580.115*
H15B0.65980.14080.12060.115*
H15C0.49540.08890.05300.115*
C160.3070 (2)0.50315 (16)0.14180 (14)0.0472 (4)
C170.1677 (3)0.56849 (19)0.11844 (16)0.0567 (5)
H170.06500.53110.09080.068*
C180.1773 (3)0.6870 (2)0.13506 (18)0.0649 (5)
H180.08190.72780.11850.078*
C190.3270 (3)0.74446 (19)0.17598 (18)0.0646 (6)
H190.33520.82410.18830.078*
C200.4643 (3)0.68013 (18)0.19809 (16)0.0586 (5)
N210.6288 (3)0.7408 (2)0.23596 (19)0.0862 (7)
O220.7586 (3)0.6863 (2)0.2372 (2)0.1137 (8)
O230.6306 (4)0.8442 (2)0.2582 (3)0.1482 (11)
C240.4578 (3)0.56196 (18)0.18234 (16)0.0561 (5)
H240.55420.52210.19880.067*
C250.0016 (2)0.31102 (16)0.21594 (15)0.0483 (4)
O260.09065 (18)0.30536 (16)0.13356 (12)0.0714 (5)
C270.0520 (2)0.32635 (15)0.33292 (15)0.0459 (4)
C280.2186 (3)0.32476 (18)0.37410 (18)0.0579 (5)
H280.31530.31090.32700.069*
C290.2339 (3)0.34456 (19)0.48762 (19)0.0647 (6)
H290.34330.34550.51780.078*
C300.0903 (3)0.36305 (18)0.55766 (17)0.0620 (5)
H300.10560.37390.63420.074*
C310.0754 (3)0.36588 (16)0.51733 (15)0.0520 (4)
H310.17140.37940.56490.062*
C320.0924 (2)0.34762 (15)0.40279 (14)0.0441 (4)
C330.2507 (2)0.35300 (14)0.33584 (14)0.0412 (4)
O340.39307 (16)0.38840 (12)0.36893 (11)0.0534 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0585 (10)0.0641 (10)0.0556 (10)0.0203 (8)0.0027 (7)0.0167 (8)
C20.0564 (11)0.0596 (12)0.0483 (10)0.0072 (9)0.0011 (8)0.0149 (8)
O30.0861 (11)0.0806 (11)0.0447 (8)0.0177 (8)0.0061 (7)0.0126 (7)
C40.0441 (9)0.0506 (10)0.0421 (9)0.0051 (7)0.0009 (7)0.0107 (7)
C50.0421 (9)0.0410 (9)0.0512 (10)0.0021 (7)0.0019 (7)0.0080 (7)
C60.0475 (10)0.0491 (10)0.0601 (11)0.0002 (8)0.0059 (8)0.0027 (8)
C70.0646 (12)0.0580 (12)0.0598 (12)0.0097 (9)0.0034 (9)0.0050 (9)
C80.0715 (14)0.0496 (11)0.0726 (14)0.0042 (10)0.0138 (11)0.0033 (10)
C90.0609 (12)0.0488 (11)0.0732 (14)0.0101 (9)0.0122 (10)0.0095 (10)
C100.0459 (10)0.0485 (10)0.0550 (11)0.0038 (8)0.0042 (8)0.0126 (8)
C110.0408 (9)0.0498 (9)0.0383 (8)0.0032 (7)0.0002 (6)0.0036 (7)
C120.0508 (10)0.0585 (11)0.0387 (9)0.0041 (8)0.0023 (7)0.0006 (8)
C130.0666 (13)0.0662 (13)0.0630 (13)0.0032 (10)0.0252 (10)0.0001 (10)
N140.0458 (8)0.0477 (8)0.0546 (9)0.0022 (6)0.0095 (7)0.0103 (7)
C150.0667 (14)0.0587 (13)0.1022 (18)0.0031 (10)0.0252 (13)0.0224 (12)
C160.0487 (10)0.0573 (11)0.0351 (8)0.0028 (8)0.0027 (7)0.0044 (7)
C170.0505 (11)0.0714 (13)0.0474 (10)0.0001 (9)0.0016 (8)0.0006 (9)
C180.0652 (13)0.0691 (14)0.0622 (13)0.0144 (10)0.0093 (10)0.0069 (10)
C190.0789 (15)0.0565 (12)0.0578 (12)0.0006 (11)0.0166 (10)0.0014 (9)
C200.0651 (12)0.0630 (13)0.0452 (10)0.0139 (10)0.0008 (9)0.0018 (9)
N210.0834 (16)0.0845 (16)0.0854 (15)0.0264 (13)0.0166 (12)0.0011 (12)
O220.0803 (14)0.1120 (17)0.145 (2)0.0256 (12)0.0423 (13)0.0251 (14)
O230.139 (2)0.0982 (18)0.193 (3)0.0374 (15)0.0220 (19)0.0522 (18)
C240.0511 (11)0.0657 (13)0.0512 (11)0.0017 (9)0.0047 (8)0.0100 (9)
C250.0425 (9)0.0546 (10)0.0468 (10)0.0028 (8)0.0010 (7)0.0027 (8)
O260.0492 (8)0.1128 (13)0.0504 (8)0.0042 (8)0.0107 (6)0.0035 (8)
C270.0438 (9)0.0478 (10)0.0465 (10)0.0035 (7)0.0033 (7)0.0048 (7)
C280.0459 (10)0.0640 (12)0.0650 (12)0.0042 (9)0.0076 (9)0.0114 (10)
C290.0605 (13)0.0664 (13)0.0685 (13)0.0044 (10)0.0236 (10)0.0080 (10)
C300.0847 (15)0.0540 (11)0.0485 (11)0.0050 (10)0.0223 (10)0.0049 (9)
C310.0650 (12)0.0490 (10)0.0420 (9)0.0045 (8)0.0026 (8)0.0020 (8)
C320.0481 (9)0.0413 (9)0.0430 (9)0.0043 (7)0.0039 (7)0.0018 (7)
C330.0430 (9)0.0394 (8)0.0405 (8)0.0022 (7)0.0017 (7)0.0019 (7)
O340.0449 (7)0.0613 (8)0.0513 (7)0.0023 (6)0.0056 (5)0.0105 (6)
Geometric parameters (Å, º) top
N1—C21.355 (3)C15—H15B0.9600
N1—C101.399 (3)C15—H15C0.9600
N1—H10.8600C16—C241.384 (3)
C2—O31.221 (2)C16—C171.396 (3)
C2—C41.573 (2)C17—C181.382 (3)
C4—N141.451 (2)C17—H170.9300
C4—C51.504 (3)C18—C191.372 (3)
C4—C111.574 (3)C18—H180.9300
C5—C61.379 (3)C19—C201.372 (3)
C5—C101.396 (2)C19—H190.9300
C6—C71.384 (3)C20—C241.378 (3)
C6—H60.9300C20—N211.471 (3)
C7—C81.382 (3)N21—O231.220 (3)
C7—H70.9300N21—O221.226 (3)
C8—C91.381 (3)C24—H240.9300
C8—H80.9300C25—O261.206 (2)
C9—C101.378 (3)C25—C271.475 (3)
C9—H90.9300C27—C321.387 (2)
C11—C331.536 (2)C27—C281.393 (3)
C11—C251.542 (2)C28—C291.376 (3)
C11—C121.548 (2)C28—H280.9300
C12—C161.516 (3)C29—C301.381 (3)
C12—C131.531 (3)C29—H290.9300
C12—H120.9800C30—C311.382 (3)
C13—N141.456 (3)C30—H300.9300
C13—H13A0.9700C31—C321.388 (2)
C13—H13B0.9700C31—H310.9300
N14—C151.454 (3)C32—C331.480 (2)
C15—H15A0.9600C33—O341.206 (2)
C2—N1—C10112.19 (15)N14—C15—H15A109.5
C2—N1—H1123.9N14—C15—H15B109.5
C10—N1—H1123.9H15A—C15—H15B109.5
O3—C2—N1126.58 (17)N14—C15—H15C109.5
O3—C2—C4126.19 (18)H15A—C15—H15C109.5
N1—C2—C4107.21 (16)H15B—C15—H15C109.5
N14—C4—C5114.48 (15)C24—C16—C17117.19 (19)
N14—C4—C2115.57 (15)C24—C16—C12123.33 (17)
C5—C4—C2101.12 (14)C17—C16—C12119.48 (16)
N14—C4—C11100.67 (13)C18—C17—C16122.23 (19)
C5—C4—C11116.09 (14)C18—C17—H17118.9
C2—C4—C11109.50 (15)C16—C17—H17118.9
C6—C5—C10119.36 (18)C19—C18—C17120.2 (2)
C6—C5—C4131.39 (15)C19—C18—H18119.9
C10—C5—C4109.24 (15)C17—C18—H18119.9
C5—C6—C7119.17 (17)C18—C19—C20117.5 (2)
C5—C6—H6120.4C18—C19—H19121.2
C7—C6—H6120.4C20—C19—H19121.2
C8—C7—C6120.5 (2)C19—C20—C24123.37 (19)
C8—C7—H7119.8C19—C20—N21118.3 (2)
C6—C7—H7119.8C24—C20—N21118.3 (2)
C9—C8—C7121.4 (2)O23—N21—O22123.4 (2)
C9—C8—H8119.3O23—N21—C20118.1 (3)
C7—C8—H8119.3O22—N21—C20118.4 (2)
C10—C9—C8117.55 (18)C20—C24—C16119.52 (19)
C10—C9—H9121.2C20—C24—H24120.2
C8—C9—H9121.2C16—C24—H24120.2
C9—C10—C5122.03 (18)O26—C25—C27126.87 (17)
C9—C10—N1128.50 (17)O26—C25—C11125.03 (17)
C5—C10—N1109.41 (17)C27—C25—C11108.06 (14)
C33—C11—C25102.15 (13)C32—C27—C28121.68 (17)
C33—C11—C12116.40 (14)C32—C27—C25109.87 (15)
C25—C11—C12114.49 (15)C28—C27—C25128.42 (17)
C33—C11—C4108.53 (13)C29—C28—C27116.99 (19)
C25—C11—C4113.69 (14)C29—C28—H28121.5
C12—C11—C4101.90 (14)C27—C28—H28121.5
C16—C12—C13117.70 (16)C28—C29—C30121.43 (19)
C16—C12—C11114.71 (14)C28—C29—H29119.3
C13—C12—C11104.40 (16)C30—C29—H29119.3
C16—C12—H12106.4C29—C30—C31121.89 (18)
C13—C12—H12106.4C29—C30—H30119.1
C11—C12—H12106.4C31—C30—H30119.1
N14—C13—C12106.28 (15)C30—C31—C32117.21 (18)
N14—C13—H13A110.5C30—C31—H31121.4
C12—C13—H13A110.5C32—C31—H31121.4
N14—C13—H13B110.5C27—C32—C31120.76 (17)
C12—C13—H13B110.5C27—C32—C33109.97 (15)
H13A—C13—H13B108.7C31—C32—C33129.18 (17)
C4—N14—C15116.02 (16)O34—C33—C32126.16 (16)
C4—N14—C13109.10 (16)O34—C33—C11126.14 (16)
C15—N14—C13114.71 (17)C32—C33—C11107.69 (14)
C10—N1—C2—O3171.0 (2)C12—C13—N14—C15154.39 (17)
C10—N1—C2—C47.5 (2)C13—C12—C16—C2425.3 (3)
O3—C2—C4—N1445.3 (3)C11—C12—C16—C2498.2 (2)
N1—C2—C4—N14133.19 (18)C13—C12—C16—C17154.07 (18)
O3—C2—C4—C5169.5 (2)C11—C12—C16—C1782.5 (2)
N1—C2—C4—C59.0 (2)C24—C16—C17—C180.3 (3)
O3—C2—C4—C1167.4 (3)C12—C16—C17—C18179.68 (17)
N1—C2—C4—C11114.04 (18)C16—C17—C18—C190.1 (3)
N14—C4—C5—C646.0 (3)C17—C18—C19—C200.6 (3)
C2—C4—C5—C6170.9 (2)C18—C19—C20—C240.7 (3)
C11—C4—C5—C670.7 (2)C18—C19—C20—N21176.60 (19)
N14—C4—C5—C10132.51 (16)C19—C20—N21—O238.3 (4)
C2—C4—C5—C107.57 (19)C24—C20—N21—O23174.3 (3)
C11—C4—C5—C10110.79 (17)C19—C20—N21—O22167.6 (2)
C10—C5—C6—C72.1 (3)C24—C20—N21—O229.9 (3)
C4—C5—C6—C7179.57 (19)C19—C20—C24—C160.3 (3)
C5—C6—C7—C80.3 (3)N21—C20—C24—C16177.01 (18)
C6—C7—C8—C91.3 (3)C17—C16—C24—C200.2 (3)
C7—C8—C9—C101.0 (3)C12—C16—C24—C20179.58 (17)
C8—C9—C10—C50.9 (3)C33—C11—C25—O26164.22 (19)
C8—C9—C10—N1175.9 (2)C12—C11—C25—O2637.5 (3)
C6—C5—C10—C92.4 (3)C4—C11—C25—O2679.1 (2)
C4—C5—C10—C9178.85 (18)C33—C11—C25—C2713.39 (18)
C6—C5—C10—N1174.91 (17)C12—C11—C25—C27140.10 (15)
C4—C5—C10—N13.8 (2)C4—C11—C25—C27103.32 (16)
C2—N1—C10—C9174.5 (2)O26—C25—C27—C32170.3 (2)
C2—N1—C10—C52.6 (2)C11—C25—C27—C327.3 (2)
N14—C4—C11—C3382.95 (15)O26—C25—C27—C287.8 (3)
C5—C4—C11—C3341.22 (19)C11—C25—C27—C28174.64 (18)
C2—C4—C11—C33154.87 (14)C32—C27—C28—C290.4 (3)
N14—C4—C11—C25164.13 (14)C25—C27—C28—C29178.27 (19)
C5—C4—C11—C2571.70 (18)C27—C28—C29—C301.2 (3)
C2—C4—C11—C2541.95 (19)C28—C29—C30—C311.9 (3)
N14—C4—C11—C1240.41 (15)C29—C30—C31—C320.9 (3)
C5—C4—C11—C12164.58 (14)C28—C27—C32—C311.3 (3)
C2—C4—C11—C1281.76 (16)C25—C27—C32—C31179.54 (16)
C33—C11—C12—C1640.2 (2)C28—C27—C32—C33175.65 (16)
C25—C11—C12—C1678.79 (19)C25—C27—C32—C332.6 (2)
C4—C11—C12—C16158.03 (15)C30—C31—C32—C270.6 (3)
C33—C11—C12—C1390.10 (18)C30—C31—C32—C33175.68 (17)
C25—C11—C12—C13150.94 (16)C27—C32—C33—O34166.96 (17)
C4—C11—C12—C1327.76 (17)C31—C32—C33—O349.7 (3)
C16—C12—C13—N14133.65 (17)C27—C32—C33—C1111.45 (19)
C11—C12—C13—N145.2 (2)C31—C32—C33—C11171.91 (17)
C5—C4—N14—C1563.9 (2)C25—C11—C33—O34163.61 (17)
C2—C4—N14—C1553.0 (3)C12—C11—C33—O3438.1 (3)
C11—C4—N14—C15170.79 (18)C4—C11—C33—O3476.0 (2)
C5—C4—N14—C13164.67 (15)C25—C11—C33—C3214.80 (17)
C2—C4—N14—C1378.4 (2)C12—C11—C33—C32140.27 (15)
C11—C4—N14—C1339.40 (17)C4—C11—C33—C32105.57 (15)
C12—C13—N14—C422.3 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O3i0.862.122.949 (2)162
C28—H28···O34ii0.932.543.150 (2)124
C31—H31···O22iii0.932.603.296 (3)133
C19—H19···O230.932.422.703 (4)98
C24—H24···O220.932.432.717 (3)98
Symmetry codes: (i) x, y, z; (ii) x1, y, z; (iii) x+1, y+1, z+1.
 

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