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In the title compound, C29H23NO2, the quinolinone moiety is planar and the pyran ring is in a half-chair form. The cyclo­pentene fused with the pyran ring adopts an envelope conformation. There are C—H...O, C—H...π and π...π intermolecular interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680402135X/ob6416sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680402135X/ob6416Isup2.hkl
Contains datablock I

CCDC reference: 252972

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.059
  • wR factor = 0.132
  • Data-to-parameter ratio = 14.7

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT022_ALERT_3_B Ratio Unique / Expected Reflections too Low .... 0.90 PLAT480_ALERT_4_B Long H...A H-Bond Reported H19 .. CG3 .. 3.29 Ang.
Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.76 Ratio PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors for C27 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for C25 PLAT480_ALERT_4_C Long H...A H-Bond Reported H29 .. O2 .. 2.68 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H24B .. CG1 .. 3.03 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H27 .. CG2 .. 3.09 Ang. PLAT481_ALERT_4_C Long D...A H-Bond Reported C27 .. CG2 .. 3.91 Ang. PLAT481_ALERT_4_C Long D...A H-Bond Reported C19 .. CG3 .. 4.03 Ang.
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 9 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 3 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 7 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: ZORTEP (Zsolnai, 1998) and PLATON (Spek,1999); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

5-Benzyl-8-(E)-benzylidene-6,7,7a,10a-tetrahydro-5H-cis- cyclopenta[5,6]pyrano[3,3-c]quinolin-6-one top
Crystal data top
C29H23NO2Z = 2
Mr = 417.48F(000) = 440
Triclinic, P1Dx = 1.280 Mg m3
a = 8.422 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.585 (3) ÅCell parameters from 4237 reflections
c = 12.866 (3) Åθ = 2.0–26.9°
α = 79.879 (4)°µ = 0.08 mm1
β = 76.281 (4)°T = 273 K
γ = 79.042 (4)°Needle, yellow
V = 1083.6 (5) Å30.32 × 0.20 × 0.12 mm
Data collection top
Siemens SMART CCD area detector
diffractometer
3097 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.019
Graphite monochromatorθmax = 26.9°, θmin = 2.0°
ω scansh = 1010
10877 measured reflectionsk = 1212
4237 independent reflectionsl = 1516
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)] = 0.059Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132H-atom parameters constrained
S = 1.12 w = 1/[σ2(Fo2) + (0.0477P)2 + 0.1865P]
where P = (Fo2 + 2Fc2)/3
4237 reflections(Δ/σ)max = 0.001
289 parametersΔρmax = 0.13 e Å3
0 restraintsΔρmin = 0.14 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
N10.20520 (19)0.32471 (14)0.95421 (12)0.0554 (4)
C90.1964 (2)0.41559 (17)1.02249 (15)0.0518 (4)
C100.2808 (2)0.52233 (17)0.98468 (14)0.0513 (4)
O10.44255 (18)0.64358 (14)0.84335 (11)0.0750 (4)
C60.3687 (2)0.53649 (18)0.87361 (15)0.0544 (5)
O20.30156 (19)0.25164 (13)0.79052 (11)0.0744 (4)
C70.3755 (2)0.44887 (18)0.80770 (14)0.0537 (5)
C20.1035 (2)0.40318 (19)1.12874 (16)0.0622 (5)
H20.04650.33311.15480.075*
C80.2947 (2)0.33574 (18)0.84765 (15)0.0563 (5)
C50.2729 (2)0.61186 (19)1.05447 (16)0.0609 (5)
H50.33020.68201.03020.073*
C40.1819 (3)0.5977 (2)1.15801 (17)0.0683 (6)
H40.17770.65781.20370.082*
C180.0615 (2)0.70600 (18)0.53506 (14)0.0570 (5)
C170.2144 (3)0.64059 (19)0.56924 (14)0.0611 (5)
H170.24820.55530.55510.073*
C160.3123 (2)0.68508 (19)0.61759 (15)0.0593 (5)
C240.1094 (3)0.2177 (2)0.99109 (17)0.0684 (6)
H24A0.10870.17770.92900.082*
H24B0.00400.25331.02070.082*
C30.0965 (3)0.4939 (2)1.19429 (17)0.0686 (6)
H30.03330.48531.26430.082*
C110.4694 (3)0.4650 (2)0.69327 (16)0.0675 (6)
H11A0.41900.42570.64910.081*
H11B0.58230.42100.68940.081*
C130.5041 (3)0.6874 (2)0.72922 (17)0.0705 (6)
H130.62240.69230.71540.085*
C190.0462 (3)0.8065 (2)0.58338 (16)0.0677 (6)
H190.02230.83550.64130.081*
C220.1248 (3)0.7191 (2)0.41517 (18)0.0753 (6)
H220.15120.68890.35870.090*
C230.0170 (3)0.6628 (2)0.45145 (16)0.0665 (5)
H230.08480.59400.41920.080*
C250.1706 (3)0.11366 (18)1.07464 (16)0.0626 (5)
C210.2271 (3)0.8202 (2)0.46249 (19)0.0776 (7)
H210.32250.85910.43780.093*
C120.4700 (2)0.6084 (2)0.64994 (16)0.0656 (5)
H120.55940.61380.58550.079*
C150.3000 (3)0.8145 (2)0.64520 (18)0.0726 (6)
H150.22510.88560.62440.087*
C200.1877 (3)0.8636 (2)0.5468 (2)0.0778 (6)
H200.25700.93180.57910.093*
C140.4083 (3)0.8186 (2)0.70346 (19)0.0778 (6)
H140.42300.89380.72560.093*
C300.3324 (3)0.0868 (2)1.08468 (19)0.0817 (7)
H300.40890.13631.04030.098*
C280.2730 (7)0.0854 (3)1.2265 (3)0.1338 (16)
H280.30760.15321.27680.161*
C270.1119 (6)0.0581 (3)1.2192 (3)0.1415 (16)
H270.03550.10581.26600.170*
C260.0600 (4)0.0398 (2)1.1427 (2)0.0977 (8)
H260.05040.05601.13710.117*
C290.3831 (4)0.0138 (2)1.1607 (2)0.1077 (10)
H290.49350.03191.16620.129*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0598 (10)0.0533 (9)0.0556 (9)0.0106 (7)0.0229 (8)0.0023 (7)
C90.0496 (10)0.0534 (11)0.0521 (11)0.0016 (9)0.0219 (9)0.0016 (9)
C100.0493 (10)0.0517 (11)0.0535 (11)0.0026 (8)0.0219 (9)0.0006 (9)
O10.0911 (11)0.0740 (9)0.0645 (9)0.0353 (8)0.0172 (8)0.0035 (7)
C60.0505 (11)0.0542 (11)0.0588 (12)0.0085 (9)0.0217 (9)0.0055 (9)
O20.1006 (11)0.0639 (9)0.0666 (9)0.0091 (8)0.0334 (8)0.0121 (7)
C70.0529 (11)0.0554 (11)0.0513 (11)0.0007 (9)0.0200 (9)0.0007 (9)
C20.0604 (12)0.0598 (12)0.0614 (12)0.0043 (9)0.0158 (10)0.0039 (10)
C80.0611 (12)0.0543 (11)0.0567 (12)0.0004 (9)0.0297 (10)0.0018 (9)
C50.0659 (13)0.0552 (11)0.0650 (13)0.0063 (9)0.0275 (10)0.0018 (10)
C40.0817 (15)0.0660 (13)0.0588 (13)0.0004 (11)0.0246 (11)0.0125 (10)
C180.0689 (13)0.0574 (11)0.0434 (10)0.0191 (10)0.0114 (9)0.0063 (9)
C170.0744 (13)0.0592 (12)0.0450 (10)0.0101 (10)0.0098 (10)0.0013 (9)
C160.0631 (12)0.0615 (12)0.0469 (10)0.0134 (10)0.0078 (9)0.0083 (9)
C240.0669 (13)0.0703 (13)0.0753 (14)0.0230 (11)0.0250 (11)0.0023 (11)
C30.0741 (14)0.0683 (14)0.0559 (12)0.0033 (11)0.0129 (10)0.0049 (11)
C110.0649 (13)0.0699 (13)0.0588 (12)0.0026 (10)0.0120 (10)0.0005 (10)
C130.0602 (12)0.0804 (15)0.0689 (14)0.0244 (11)0.0148 (10)0.0118 (11)
C190.0703 (14)0.0752 (14)0.0592 (12)0.0142 (11)0.0154 (11)0.0076 (11)
C220.0930 (17)0.0784 (15)0.0623 (13)0.0336 (14)0.0293 (12)0.0093 (12)
C230.0825 (15)0.0643 (13)0.0530 (12)0.0204 (11)0.0163 (11)0.0033 (10)
C250.0788 (14)0.0487 (11)0.0617 (12)0.0173 (10)0.0115 (11)0.0080 (9)
C210.0706 (15)0.0826 (16)0.0797 (16)0.0249 (13)0.0288 (12)0.0204 (13)
C120.0571 (12)0.0761 (14)0.0544 (12)0.0087 (10)0.0059 (9)0.0055 (10)
C150.0758 (15)0.0609 (13)0.0830 (15)0.0177 (11)0.0265 (12)0.0059 (11)
C200.0682 (14)0.0760 (15)0.0853 (16)0.0088 (12)0.0160 (13)0.0036 (12)
C140.0820 (16)0.0676 (14)0.0901 (16)0.0293 (12)0.0288 (13)0.0058 (12)
C300.0990 (18)0.0645 (14)0.0885 (16)0.0211 (13)0.0420 (14)0.0106 (12)
C280.266 (5)0.0479 (16)0.0765 (19)0.000 (3)0.039 (3)0.0016 (14)
C270.215 (4)0.0536 (18)0.107 (2)0.022 (2)0.048 (3)0.0085 (16)
C260.105 (2)0.0589 (14)0.111 (2)0.0228 (13)0.0191 (16)0.0093 (14)
C290.167 (3)0.0622 (15)0.110 (2)0.0027 (18)0.078 (2)0.0032 (16)
Geometric parameters (Å, º) top
N1—C91.393 (2)C11—C121.523 (3)
N1—C81.396 (2)C11—H11A0.9700
N1—C241.461 (2)C11—H11B0.9700
C9—C21.402 (3)C13—C141.493 (3)
C9—C101.402 (2)C13—C121.533 (3)
C10—C51.398 (3)C13—H130.9800
C10—C61.442 (3)C19—C201.378 (3)
O1—C61.350 (2)C19—H190.9300
O1—C131.460 (2)C22—C211.374 (3)
C6—C71.348 (3)C22—C231.376 (3)
O2—C81.235 (2)C22—H220.9300
C7—C81.445 (3)C23—H230.9300
C7—C111.494 (3)C25—C301.370 (3)
C2—C31.370 (3)C25—C261.376 (3)
C2—H20.9300C21—C201.379 (3)
C5—C41.369 (3)C21—H210.9300
C5—H50.9300C12—H120.9800
C4—C31.380 (3)C15—C141.322 (3)
C4—H40.9300C15—H150.9300
C18—C231.392 (3)C20—H200.9300
C18—C191.393 (3)C14—H140.9300
C18—C171.467 (3)C30—C291.390 (3)
C17—C161.335 (3)C30—H300.9300
C17—H170.9300C28—C291.349 (5)
C16—C151.454 (3)C28—C271.355 (5)
C16—C121.526 (3)C28—H280.9300
C24—C251.505 (3)C27—C261.381 (4)
C24—H24A0.9700C27—H270.9300
C24—H24B0.9700C26—H260.9300
C3—H30.9300C29—H290.9300
C9—N1—C8122.49 (16)O1—C13—C14106.89 (18)
C9—N1—C24119.90 (17)O1—C13—C12115.44 (16)
C8—N1—C24117.48 (16)C14—C13—C12103.15 (17)
N1—C9—C2121.32 (17)O1—C13—H13110.3
N1—C9—C10119.74 (17)C14—C13—H13110.3
C2—C9—C10118.94 (18)C12—C13—H13110.3
C5—C10—C9119.20 (18)C20—C19—C18121.1 (2)
C5—C10—C6122.84 (17)C20—C19—H19119.5
C9—C10—C6117.94 (17)C18—C19—H19119.5
C6—O1—C13120.41 (16)C21—C22—C23119.9 (2)
C7—C6—O1124.07 (18)C21—C22—H22120.1
C7—C6—C10121.97 (17)C23—C22—H22120.1
O1—C6—C10113.96 (17)C22—C23—C18121.8 (2)
C6—C7—C8120.26 (17)C22—C23—H23119.1
C6—C7—C11120.87 (18)C18—C23—H23119.1
C8—C7—C11118.86 (18)C30—C25—C26118.3 (2)
C3—C2—C9120.25 (19)C30—C25—C24123.09 (19)
C3—C2—H2119.9C26—C25—C24118.6 (2)
C9—C2—H2119.9C22—C21—C20119.7 (2)
O2—C8—N1120.32 (18)C22—C21—H21120.2
O2—C8—C7122.17 (19)C20—C21—H21120.2
N1—C8—C7117.51 (17)C11—C12—C16117.12 (17)
C4—C5—C10120.92 (19)C11—C12—C13113.70 (17)
C4—C5—H5119.5C16—C12—C13103.85 (17)
C10—C5—H5119.5C11—C12—H12107.2
C5—C4—C3119.7 (2)C16—C12—H12107.2
C5—C4—H4120.1C13—C12—H12107.2
C3—C4—H4120.1C14—C15—C16111.6 (2)
C23—C18—C19117.20 (19)C14—C15—H15124.2
C23—C18—C17118.51 (19)C16—C15—H15124.2
C19—C18—C17124.25 (18)C19—C20—C21120.3 (2)
C16—C17—C18129.74 (19)C19—C20—H20119.8
C16—C17—H17115.1C21—C20—H20119.8
C18—C17—H17115.1C15—C14—C13111.6 (2)
C17—C16—C15128.92 (19)C15—C14—H14124.2
C17—C16—C12125.62 (19)C13—C14—H14124.2
C15—C16—C12105.38 (17)C25—C30—C29120.6 (3)
N1—C24—C25115.49 (16)C25—C30—H30119.7
N1—C24—H24A108.4C29—C30—H30119.7
C25—C24—H24A108.4C29—C28—C27119.7 (3)
N1—C24—H24B108.4C29—C28—H28120.1
C25—C24—H24B108.4C27—C28—H28120.1
H24A—C24—H24B107.5C28—C27—C26120.7 (3)
C2—C3—C4121.0 (2)C28—C27—H27119.7
C2—C3—H3119.5C26—C27—H27119.7
C4—C3—H3119.5C25—C26—C27120.4 (3)
C7—C11—C12110.47 (17)C25—C26—H26119.8
C7—C11—H11A109.6C27—C26—H26119.8
C12—C11—H11A109.6C28—C29—C30120.3 (3)
C7—C11—H11B109.6C28—C29—H29119.8
C12—C11—H11B109.6C30—C29—H29119.8
H11A—C11—H11B108.1
C8—N1—C9—C2179.04 (15)C5—C4—C3—C21.1 (3)
C24—N1—C9—C23.3 (2)C6—C7—C11—C1229.8 (2)
C8—N1—C9—C100.6 (2)C8—C7—C11—C12151.59 (17)
C24—N1—C9—C10176.29 (15)C6—O1—C13—C14117.20 (19)
N1—C9—C10—C5179.09 (15)C6—O1—C13—C123.1 (3)
C2—C9—C10—C51.3 (2)C23—C18—C19—C202.4 (3)
N1—C9—C10—C62.6 (2)C17—C18—C19—C20179.88 (19)
C2—C9—C10—C6177.01 (15)C21—C22—C23—C180.5 (3)
C13—O1—C6—C714.2 (3)C19—C18—C23—C222.0 (3)
C13—O1—C6—C10166.20 (16)C17—C18—C23—C22179.86 (18)
C5—C10—C6—C7179.72 (16)N1—C24—C25—C3026.4 (3)
C9—C10—C6—C72.1 (2)N1—C24—C25—C26155.1 (2)
C5—C10—C6—O10.1 (2)C23—C22—C21—C200.6 (3)
C9—C10—C6—O1178.32 (15)C7—C11—C12—C1677.2 (2)
O1—C6—C7—C8178.99 (16)C7—C11—C12—C1344.0 (2)
C10—C6—C7—C80.6 (3)C17—C16—C12—C1137.8 (3)
O1—C6—C7—C110.4 (3)C15—C16—C12—C11145.18 (18)
C10—C6—C7—C11179.16 (16)C17—C16—C12—C13164.09 (18)
N1—C9—C2—C3179.91 (17)C15—C16—C12—C1318.92 (19)
C10—C9—C2—C30.3 (3)O1—C13—C12—C1132.5 (3)
C9—N1—C8—O2178.71 (16)C14—C13—C12—C11148.68 (17)
C24—N1—C8—O25.5 (2)O1—C13—C12—C1695.91 (19)
C9—N1—C8—C72.1 (2)C14—C13—C12—C1620.3 (2)
C24—N1—C8—C7173.75 (15)C17—C16—C15—C14172.9 (2)
C6—C7—C8—O2178.16 (17)C12—C16—C15—C1410.3 (2)
C11—C7—C8—O20.4 (3)C18—C19—C20—C211.4 (3)
C6—C7—C8—N12.6 (2)C22—C21—C20—C190.2 (3)
C11—C7—C8—N1178.78 (15)C16—C15—C14—C133.5 (3)
C9—C10—C5—C41.1 (3)O1—C13—C14—C15106.7 (2)
C6—C10—C5—C4177.08 (17)C12—C13—C14—C1515.4 (2)
C10—C5—C4—C30.1 (3)C26—C25—C30—C290.9 (3)
C23—C18—C17—C16154.9 (2)C24—C25—C30—C29177.5 (2)
C19—C18—C17—C1627.4 (3)C29—C28—C27—C261.9 (5)
C18—C17—C16—C153.7 (3)C30—C25—C26—C270.3 (4)
C18—C17—C16—C12179.96 (17)C24—C25—C26—C27178.9 (2)
C9—N1—C24—C2572.0 (2)C28—C27—C26—C251.8 (5)
C8—N1—C24—C25112.0 (2)C27—C28—C29—C300.7 (5)
C9—C2—C3—C40.9 (3)C25—C30—C29—C280.8 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C24—H24A···O20.972.252.706 (2)108
C22—H22···O2i0.932.473.275 (3)145
C29—H29···O2ii0.932.683.388 (3)134
C24—H24B···Cg1iii0.973.033.642123
C27—H27···Cg2iv0.933.093.906147
C19—H19···Cg3iii0.933.294.033138
Symmetry codes: (i) x, y+1, z+1; (ii) x+1, y, z+2; (iii) x, y+1, z+2; (iv) x, y1, z+1.
 

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