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In the title compound, C22H15NO3, the quinoline system is essentially planar, and the mean plane of the indenone ring system is almost coplanar with the quinoline group. The crystal structure is stabilized by inter- and intra­molecular C—H...O hydrogen-bonding inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807001183/at2201sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807001183/at2201Isup2.hkl
Contains datablock I

CCDC reference: 636118

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.052
  • wR factor = 0.128
  • Data-to-parameter ratio = 12.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 3000 Deg. PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.96 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.02 Ratio
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 0 ALERT type 5 Informative message, check

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

Ethyl 7-oxo-7H-indeno[2',1':3,4]pyrrolo[2,1-a]quinoline-12-carboxylate top
Crystal data top
C22H15NO3Z = 2
Mr = 341.35F(000) = 356
Triclinic, P1Dx = 1.399 Mg m3
Hall symbol: -P 1Melting point: 466 K
a = 7.5210 (15) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.4560 (19) ÅCell parameters from 25 reflections
c = 12.411 (3) Åθ = 2.4–23.5°
α = 99.33 (3)°µ = 0.09 mm1
β = 98.15 (3)°T = 293 K
γ = 108.13 (3)°Block, yellow
V = 810.2 (4) Å30.40 × 0.30 × 0.20 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer
1941 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.020
Graphite monochromatorθmax = 25.0°, θmin = 1.7°
ω/2θ scansh = 08
Absorption correction: ψ scan
(XCAD4; Harms & Wocadlo, 1995)
k = 1110
Tmin = 0.872, Tmax = 0.973l = 1414
3086 measured reflections3 standard reflections every 200 reflections
2847 independent reflections intensity decay: none
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.052H-atom parameters constrained
wR(F2) = 0.129 w = 1/[σ2(Fo2) + (0.057P)2 + 0.2168P]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
2847 reflectionsΔρmax = 0.22 e Å3
236 parametersΔρmin = 0.18 e Å3
0 restraintsExtinction correction: SHELXTL (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.025 (3)
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
O10.2088 (2)0.17891 (17)0.21912 (13)0.0420 (4)
O20.2428 (3)0.18223 (19)0.04241 (14)0.0561 (5)
O30.5318 (3)0.92222 (19)0.19536 (15)0.0628 (6)
N0.5239 (3)0.47353 (19)0.28823 (14)0.0317 (5)
C220.0383 (6)0.0381 (4)0.2799 (3)0.0945 (13)
H22A0.04130.14350.25720.142*
H22B0.02940.01960.31650.142*
H22C0.15270.02830.33040.142*
C210.0880 (4)0.0191 (3)0.1827 (2)0.0565 (8)
H21A0.02700.00920.13100.068*
H21B0.15560.03920.14490.068*
C200.2826 (3)0.2441 (3)0.13975 (19)0.0374 (6)
C120.4034 (3)0.4040 (2)0.18111 (17)0.0319 (5)
C110.3900 (3)0.5201 (2)0.13131 (17)0.0328 (5)
C150.2928 (3)0.5481 (3)0.02935 (18)0.0346 (6)
C160.1751 (3)0.4519 (3)0.06762 (19)0.0431 (6)
H16A0.14240.34670.07780.052*
C170.1067 (4)0.5171 (3)0.1497 (2)0.0490 (7)
H17A0.02700.45390.21560.059*
C180.1538 (4)0.6721 (3)0.1358 (2)0.0536 (7)
H18A0.10600.71220.19240.064*
C190.2717 (4)0.7700 (3)0.0386 (2)0.0494 (7)
H19A0.30390.87510.02910.059*
C140.3399 (3)0.7065 (3)0.04379 (19)0.0400 (6)
C130.4685 (4)0.7855 (3)0.1565 (2)0.0418 (6)
C100.4925 (3)0.6605 (2)0.20523 (18)0.0357 (6)
C90.5751 (3)0.6312 (2)0.30277 (18)0.0341 (5)
C80.6846 (3)0.7266 (3)0.40635 (19)0.0403 (6)
H8A0.71440.83170.41780.048*
C70.7454 (3)0.6647 (3)0.4883 (2)0.0432 (6)
H7A0.81010.72690.55780.052*
C40.7117 (3)0.5046 (3)0.46972 (18)0.0371 (6)
C30.7878 (4)0.4407 (3)0.5507 (2)0.0479 (7)
H3A0.85360.50240.62020.057*
C20.7678 (4)0.2904 (3)0.5303 (2)0.0553 (7)
H2A0.81610.24920.58590.066*
C10.6750 (4)0.1989 (3)0.4258 (2)0.0508 (7)
H1A0.66540.09690.41100.061*
C60.5968 (3)0.2565 (3)0.3437 (2)0.0393 (6)
H6A0.53700.19440.27350.047*
C50.6074 (3)0.4074 (2)0.36606 (17)0.0326 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0464 (10)0.0348 (9)0.0344 (9)0.0023 (8)0.0029 (8)0.0067 (7)
O20.0713 (13)0.0489 (11)0.0298 (10)0.0039 (10)0.0032 (9)0.0027 (8)
O30.0914 (16)0.0366 (11)0.0552 (12)0.0219 (10)0.0011 (11)0.0077 (9)
N0.0367 (11)0.0312 (10)0.0245 (10)0.0101 (8)0.0030 (8)0.0041 (8)
C220.129 (3)0.0532 (19)0.069 (2)0.016 (2)0.019 (2)0.0197 (17)
C210.0635 (19)0.0360 (14)0.0531 (17)0.0016 (13)0.0021 (15)0.0086 (12)
C200.0409 (14)0.0375 (13)0.0310 (13)0.0133 (11)0.0010 (11)0.0060 (11)
C120.0345 (13)0.0346 (13)0.0234 (11)0.0109 (10)0.0029 (10)0.0021 (9)
C110.0357 (13)0.0366 (13)0.0256 (12)0.0129 (10)0.0054 (10)0.0056 (10)
C150.0344 (13)0.0409 (14)0.0305 (12)0.0136 (11)0.0090 (10)0.0101 (10)
C160.0446 (15)0.0512 (15)0.0326 (13)0.0147 (12)0.0075 (11)0.0104 (11)
C170.0491 (16)0.0685 (19)0.0303 (13)0.0229 (14)0.0022 (12)0.0125 (12)
C180.0579 (18)0.081 (2)0.0366 (15)0.0363 (16)0.0112 (14)0.0266 (14)
C190.0569 (17)0.0565 (16)0.0472 (16)0.0288 (14)0.0159 (14)0.0224 (13)
C140.0461 (15)0.0494 (15)0.0309 (13)0.0212 (12)0.0124 (11)0.0124 (11)
C130.0505 (16)0.0379 (15)0.0412 (14)0.0182 (12)0.0128 (12)0.0112 (11)
C100.0429 (14)0.0333 (13)0.0304 (12)0.0137 (11)0.0063 (11)0.0050 (10)
C90.0372 (13)0.0321 (12)0.0305 (12)0.0106 (10)0.0058 (10)0.0034 (10)
C80.0450 (15)0.0329 (13)0.0356 (13)0.0073 (11)0.0043 (11)0.0028 (10)
C70.0433 (15)0.0465 (15)0.0283 (13)0.0072 (12)0.0009 (11)0.0007 (11)
C40.0339 (13)0.0443 (14)0.0297 (12)0.0109 (11)0.0041 (10)0.0053 (11)
C30.0487 (16)0.0577 (17)0.0327 (14)0.0173 (13)0.0034 (12)0.0094 (12)
C20.0623 (19)0.0666 (19)0.0444 (16)0.0324 (15)0.0006 (14)0.0222 (14)
C10.0603 (18)0.0460 (15)0.0540 (17)0.0274 (14)0.0092 (14)0.0165 (13)
C60.0424 (14)0.0393 (14)0.0357 (13)0.0163 (11)0.0036 (11)0.0061 (11)
C50.0324 (13)0.0397 (13)0.0276 (12)0.0135 (11)0.0070 (10)0.0091 (10)
Geometric parameters (Å, º) top
O1—C201.341 (3)C18—C191.386 (4)
O1—C211.456 (3)C18—H18A0.9300
O2—C201.204 (3)C19—C141.383 (3)
O3—C131.216 (3)C19—H19A0.9300
N—C91.393 (3)C14—C131.510 (3)
N—C51.410 (3)C13—C101.459 (3)
N—C121.423 (3)C10—C91.390 (3)
C22—C211.450 (4)C9—C81.416 (3)
C22—H22A0.9600C8—C71.347 (3)
C22—H22B0.9600C8—H8A0.9300
C22—H22C0.9600C7—C41.429 (3)
C21—H21A0.9700C7—H7A0.9300
C21—H21B0.9700C4—C31.397 (3)
C20—C121.462 (3)C4—C51.413 (3)
C12—C111.367 (3)C3—C21.359 (4)
C11—C101.403 (3)C3—H3A0.9300
C11—C151.474 (3)C2—C11.386 (4)
C15—C161.379 (3)C2—H2A0.9300
C15—C141.402 (3)C1—C61.375 (3)
C16—C171.390 (3)C1—H1A0.9300
C16—H16A0.9300C6—C51.383 (3)
C17—C181.372 (4)C6—H6A0.9300
C17—H17A0.9300
C20—O1—C21115.55 (18)C14—C19—H19A121.0
C9—N—C5121.21 (18)C18—C19—H19A121.0
C9—N—C12108.63 (18)C19—C14—C15121.2 (2)
C5—N—C12129.63 (18)C19—C14—C13128.9 (2)
C21—C22—H22A109.5C15—C14—C13110.0 (2)
C21—C22—H22B109.5O3—C13—C10129.8 (2)
H22A—C22—H22B109.5O3—C13—C14126.4 (2)
C21—C22—H22C109.5C10—C13—C14103.8 (2)
H22A—C22—H22C109.5C9—C10—C11107.89 (19)
H22B—C22—H22C109.5C9—C10—C13141.7 (2)
C22—C21—O1108.5 (2)C11—C10—C13110.3 (2)
C22—C21—H21A110.0C10—C9—N107.34 (19)
O1—C21—H21A110.0C10—C9—C8133.0 (2)
C22—C21—H21B110.0N—C9—C8119.6 (2)
O1—C21—H21B110.0C7—C8—C9119.9 (2)
H21A—C21—H21B108.4C7—C8—H8A120.1
O2—C20—O1124.0 (2)C9—C8—H8A120.1
O2—C20—C12122.6 (2)C8—C7—C4120.8 (2)
O1—C20—C12113.20 (19)C8—C7—H7A119.6
C11—C12—N106.53 (18)C4—C7—H7A119.6
C11—C12—C20124.6 (2)C3—C4—C5118.1 (2)
N—C12—C20127.6 (2)C3—C4—C7121.4 (2)
C12—C11—C10109.56 (19)C5—C4—C7120.4 (2)
C12—C11—C15141.4 (2)C2—C3—C4121.4 (2)
C10—C11—C15108.83 (19)C2—C3—H3A119.3
C16—C15—C14120.4 (2)C4—C3—H3A119.3
C16—C15—C11132.6 (2)C3—C2—C1119.5 (2)
C14—C15—C11107.0 (2)C3—C2—H2A120.2
C15—C16—C17118.0 (2)C1—C2—H2A120.2
C15—C16—H16A121.0C6—C1—C2121.1 (2)
C17—C16—H16A121.0C6—C1—H1A119.5
C18—C17—C16121.6 (2)C2—C1—H1A119.5
C18—C17—H17A119.2C1—C6—C5119.6 (2)
C16—C17—H17A119.2C1—C6—H6A120.2
C17—C18—C19120.9 (2)C5—C6—H6A120.2
C17—C18—H18A119.5C6—C5—N123.2 (2)
C19—C18—H18A119.5C6—C5—C4120.0 (2)
C14—C19—C18118.0 (3)N—C5—C4116.8 (2)
C20—O1—C21—C22173.6 (3)C15—C11—C10—C9177.10 (19)
C21—O1—C20—O25.8 (4)C12—C11—C10—C13175.9 (2)
C21—O1—C20—C12179.7 (2)C15—C11—C10—C130.1 (3)
C9—N—C12—C112.3 (2)O3—C13—C10—C93.0 (5)
C5—N—C12—C11169.2 (2)C14—C13—C10—C9175.8 (3)
C9—N—C12—C20165.3 (2)O3—C13—C10—C11178.7 (3)
C5—N—C12—C2023.2 (4)C14—C13—C10—C110.1 (3)
O2—C20—C12—C1142.9 (4)C11—C10—C9—N0.3 (3)
O1—C20—C12—C11131.6 (2)C13—C10—C9—N176.0 (3)
O2—C20—C12—N151.6 (2)C11—C10—C9—C8176.5 (2)
O1—C20—C12—N33.9 (3)C13—C10—C9—C80.7 (5)
N—C12—C11—C102.2 (3)C5—N—C9—C10170.78 (19)
C20—C12—C11—C10165.9 (2)C12—N—C9—C101.6 (2)
N—C12—C11—C15175.9 (3)C5—N—C9—C812.0 (3)
C20—C12—C11—C157.8 (5)C12—N—C9—C8175.7 (2)
C12—C11—C15—C165.9 (5)C10—C9—C8—C7179.3 (3)
C10—C11—C15—C16179.7 (2)N—C9—C8—C72.9 (4)
C12—C11—C15—C14174.0 (3)C9—C8—C7—C44.2 (4)
C10—C11—C15—C140.3 (3)C8—C7—C4—C3174.5 (2)
C14—C15—C16—C170.4 (3)C8—C7—C4—C52.4 (4)
C11—C15—C16—C17179.7 (2)C5—C4—C3—C21.9 (4)
C15—C16—C17—C180.0 (4)C7—C4—C3—C2175.1 (2)
C16—C17—C18—C190.2 (4)C4—C3—C2—C11.9 (4)
C17—C18—C19—C140.1 (4)C3—C2—C1—C62.3 (4)
C18—C19—C14—C150.5 (4)C2—C1—C6—C51.3 (4)
C18—C19—C14—C13179.8 (2)C1—C6—C5—N177.2 (2)
C16—C15—C14—C190.7 (4)C1—C6—C5—C45.2 (4)
C11—C15—C14—C19179.3 (2)C9—N—C5—C6164.3 (2)
C16—C15—C14—C13179.6 (2)C12—N—C5—C66.2 (4)
C11—C15—C14—C130.4 (3)C9—N—C5—C413.4 (3)
C19—C14—C13—O31.8 (4)C12—N—C5—C4176.0 (2)
C15—C14—C13—O3178.6 (2)C3—C4—C5—C65.4 (3)
C19—C14—C13—C10179.4 (2)C7—C4—C5—C6171.6 (2)
C15—C14—C13—C100.3 (3)C3—C4—C5—N176.7 (2)
C12—C11—C10—C91.2 (3)C7—C4—C5—N6.2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6A···O10.932.422.909 (3)113
C6—H6A···O3i0.932.583.243 (3)128
C16—H16A···O20.932.523.220 (3)132
C21—H21A···O2ii0.972.543.313 (3)136
Symmetry codes: (i) x, y1, z; (ii) x, y, z.
 

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