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In the title compound, C29H23NO3, the dihedral angle between the fused rings in the tetra­hydro­naphthalene moiety is 8.0 (7)°. The pyrrolidine ring adopts an envelope conformation and is orthogonal to the tetra­hydro­naphthalene and acenaphthene rings, the dihedral angles being 89.0 (4) and 85.5 (5)°, respectively. The molecular structure and the packing are stabilized by intramolecular C—H...O interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803024711/bt6369sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803024711/bt6369Isup2.hkl
Contains datablock I

CCDC reference: 227785

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • R factor = 0.055
  • wR factor = 0.187
  • Data-to-parameter ratio = 17.5

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.95
Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for O30 - C26 = 7.44 su PLAT230_ALERT_2_B Hirshfeld Test Diff for C26 - C27 = 7.41 su PLAT230_ALERT_2_B Hirshfeld Test Diff for C27 - C28 = 11.28 su PLAT230_ALERT_2_B Hirshfeld Test Diff for C28 - C29 = 10.28 su
Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C28
1 ALERT level A = In general: serious problem 4 ALERT level B = Potentially serious problem 2 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 5 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 1 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, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1997) and PLATON (Spek, 1990); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

1,2,3,4-Tetrahydro-4'-furfuryl-1'-methylnaphthene-2-spiro-3'-pyrrolidine-2'- spiro-1''-acenaphthene-1,2''-dione top
Crystal data top
C29H23NO3F(000) = 912
Mr = 433.48Dx = 1.267 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 11.9109 (7) ÅCell parameters from 4019 reflections
b = 11.3292 (7) Åθ = 2.2–25.8°
c = 17.3573 (10) ŵ = 0.08 mm1
β = 103.993 (1)°T = 293 K
V = 2272.7 (2) Å3Needle, yellow
Z = 40.22 × 0.17 × 0.13 mm
Data collection top
CCD Area Detector
diffractometer
3529 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.022
Graphite monochromatorθmax = 28.0°, θmin = 1.8°
ω scansh = 158
14010 measured reflectionsk = 1414
5225 independent reflectionsl = 2122
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)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.187H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.1086P)2 + 0.3011P]
where P = (Fo2 + 2Fc2)/3
5225 reflections(Δ/σ)max < 0.001
298 parametersΔρmax = 0.33 e Å3
0 restraintsΔρmin = 0.25 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
N10.65564 (14)0.82744 (15)0.11365 (9)0.0613 (4)
C20.71796 (15)0.80494 (15)0.05206 (10)0.0500 (4)
C30.81151 (15)0.70973 (15)0.09329 (10)0.0486 (4)
C40.82280 (16)0.73191 (16)0.18471 (10)0.0529 (4)
H40.78950.66260.20470.064*
C50.74264 (18)0.8347 (2)0.18878 (11)0.0656 (5)
H5A0.70760.82640.23350.079*
H5B0.78390.90920.19340.079*
C60.63491 (15)0.77233 (15)0.02642 (10)0.0499 (4)
C70.55041 (17)0.69020 (18)0.04559 (12)0.0622 (5)
H70.53540.64000.00690.075*
C80.4850 (2)0.6814 (2)0.12521 (14)0.0742 (6)
H80.42740.62430.13810.089*
C90.5038 (2)0.7539 (2)0.18352 (13)0.0757 (6)
H90.46040.74450.23540.091*
C100.58824 (18)0.84282 (18)0.16562 (11)0.0619 (5)
C110.6165 (2)0.9272 (2)0.21738 (13)0.0771 (7)
H110.57910.92510.27100.093*
C120.6969 (2)1.0109 (2)0.19060 (14)0.0812 (7)
H120.71261.06540.22660.097*
C130.7585 (2)1.01967 (19)0.10996 (14)0.0732 (6)
H130.81331.07850.09270.088*
C140.73351 (17)0.93692 (16)0.05835 (11)0.0567 (5)
C150.65123 (16)0.84995 (15)0.08621 (10)0.0518 (4)
C160.77859 (18)0.91784 (16)0.02799 (12)0.0596 (5)
C170.76012 (15)0.58683 (15)0.07125 (10)0.0501 (4)
C180.77875 (17)0.52910 (17)0.00150 (11)0.0572 (5)
C190.7186 (2)0.42524 (19)0.02707 (13)0.0721 (6)
H190.67360.39050.00370.086*
C200.7256 (3)0.3733 (2)0.09830 (16)0.0906 (8)
H200.68520.30420.11550.109*
C210.7932 (3)0.4253 (3)0.14321 (15)0.0959 (9)
H210.79690.39180.19140.115*
C220.8543 (2)0.5251 (3)0.11766 (13)0.0838 (8)
H220.90030.55780.14850.101*
C230.84983 (18)0.58022 (19)0.04587 (11)0.0628 (5)
C240.91809 (19)0.6885 (2)0.01773 (13)0.0695 (6)
H24A0.88240.75510.04950.083*
H24B0.99540.67910.02570.083*
C250.92695 (17)0.71563 (19)0.06958 (12)0.0614 (5)
H25A0.95930.79400.08130.074*
H25B0.98020.66000.10180.074*
C260.94074 (17)0.74678 (16)0.23608 (11)0.0580 (5)
C270.99912 (19)0.66839 (18)0.28728 (13)0.0680 (6)
H270.97510.59220.29530.082*
C281.1035 (2)0.7211 (3)0.32708 (16)0.0969 (9)
H281.16100.68680.36670.116*
C291.1051 (2)0.8266 (3)0.29826 (16)0.0899 (8)
H291.16520.88050.31380.108*
O301.00188 (16)0.84744 (14)0.23981 (10)0.0847 (5)
C310.5751 (2)0.9259 (2)0.09961 (15)0.0866 (7)
H31A0.53920.93290.14330.130*
H31B0.51680.91240.05150.130*
H31C0.61600.99740.09470.130*
O320.84673 (16)0.97926 (14)0.07339 (10)0.0885 (5)
O330.70311 (13)0.53766 (12)0.11107 (8)0.0651 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0611 (9)0.0762 (10)0.0492 (8)0.0180 (8)0.0187 (7)0.0015 (7)
C20.0544 (10)0.0524 (9)0.0440 (9)0.0041 (7)0.0137 (7)0.0044 (7)
C30.0494 (9)0.0536 (9)0.0449 (9)0.0052 (7)0.0155 (7)0.0076 (7)
C40.0577 (10)0.0572 (10)0.0440 (9)0.0030 (8)0.0123 (7)0.0046 (7)
C50.0707 (12)0.0815 (14)0.0474 (10)0.0126 (10)0.0195 (9)0.0013 (9)
C60.0516 (10)0.0514 (9)0.0475 (9)0.0086 (7)0.0136 (7)0.0056 (7)
C70.0569 (11)0.0641 (11)0.0645 (12)0.0000 (9)0.0127 (9)0.0102 (9)
C80.0663 (13)0.0765 (14)0.0727 (14)0.0068 (11)0.0029 (10)0.0025 (11)
C90.0786 (14)0.0886 (15)0.0541 (11)0.0063 (12)0.0046 (10)0.0065 (11)
C100.0705 (12)0.0706 (12)0.0478 (10)0.0198 (10)0.0207 (9)0.0049 (8)
C110.0903 (16)0.0956 (17)0.0506 (11)0.0222 (14)0.0272 (11)0.0173 (11)
C120.0982 (17)0.0872 (16)0.0704 (14)0.0205 (14)0.0438 (13)0.0349 (12)
C130.0823 (15)0.0612 (12)0.0839 (15)0.0063 (10)0.0355 (12)0.0182 (10)
C140.0660 (11)0.0502 (10)0.0586 (10)0.0101 (8)0.0243 (9)0.0092 (8)
C150.0577 (10)0.0525 (10)0.0491 (9)0.0132 (8)0.0205 (8)0.0056 (7)
C160.0683 (12)0.0496 (10)0.0607 (11)0.0013 (9)0.0155 (9)0.0025 (8)
C170.0531 (9)0.0531 (9)0.0458 (9)0.0087 (7)0.0150 (7)0.0072 (7)
C180.0639 (11)0.0595 (11)0.0489 (9)0.0182 (9)0.0154 (8)0.0035 (8)
C190.0820 (14)0.0698 (13)0.0632 (12)0.0107 (11)0.0152 (11)0.0079 (10)
C200.106 (2)0.0851 (16)0.0752 (15)0.0218 (15)0.0112 (14)0.0227 (13)
C210.107 (2)0.120 (2)0.0596 (14)0.0396 (18)0.0182 (14)0.0211 (14)
C220.0891 (16)0.114 (2)0.0544 (12)0.0383 (15)0.0296 (11)0.0090 (12)
C230.0643 (12)0.0771 (13)0.0510 (10)0.0297 (10)0.0216 (9)0.0110 (9)
C240.0660 (12)0.0830 (14)0.0706 (13)0.0186 (11)0.0380 (10)0.0193 (11)
C250.0521 (10)0.0709 (12)0.0650 (12)0.0050 (9)0.0216 (9)0.0104 (9)
C260.0633 (11)0.0545 (10)0.0545 (10)0.0028 (8)0.0111 (8)0.0050 (8)
C270.0705 (13)0.0533 (11)0.0734 (13)0.0000 (9)0.0041 (10)0.0136 (9)
C280.0806 (17)0.122 (2)0.0781 (17)0.0121 (16)0.0006 (13)0.0120 (16)
C290.0687 (14)0.126 (2)0.0750 (15)0.0336 (15)0.0180 (12)0.0326 (15)
O300.0951 (12)0.0762 (10)0.0837 (11)0.0162 (9)0.0233 (9)0.0011 (8)
C310.0840 (16)0.1029 (18)0.0743 (14)0.0400 (14)0.0222 (12)0.0013 (12)
O320.1075 (13)0.0691 (10)0.0809 (11)0.0245 (9)0.0074 (9)0.0028 (8)
O330.0840 (9)0.0603 (8)0.0574 (8)0.0096 (7)0.0298 (7)0.0014 (6)
Geometric parameters (Å, º) top
N1—C311.453 (3)C14—C161.481 (3)
N1—C51.459 (2)C16—O321.206 (2)
N1—C21.464 (2)C17—O331.215 (2)
C2—C61.523 (2)C17—C181.486 (2)
C2—C161.574 (3)C18—C191.393 (3)
C2—C31.591 (2)C18—C231.400 (3)
C3—C251.529 (3)C19—C201.390 (3)
C3—C171.532 (2)C19—H190.9300
C3—C41.580 (2)C20—C211.381 (4)
C4—C261.480 (3)C20—H200.9300
C4—C51.519 (3)C21—C221.359 (4)
C4—H40.9800C21—H210.9300
C5—H5A0.9700C22—C231.406 (3)
C5—H5B0.9700C22—H220.9300
C6—C71.352 (3)C23—C241.488 (3)
C6—C151.409 (2)C24—C251.525 (3)
C7—C81.416 (3)C24—H24A0.9700
C7—H70.9300C24—H24B0.9700
C8—C91.363 (3)C25—H25A0.9700
C8—H80.9300C25—H25B0.9700
C9—C101.404 (3)C26—C271.328 (3)
C9—H90.9300C26—O301.346 (2)
C10—C151.403 (3)C27—C281.402 (3)
C10—C111.407 (3)C27—H270.9300
C11—C121.348 (4)C28—C291.297 (4)
C11—H110.9300C28—H280.9300
C12—C131.418 (3)C29—O301.412 (3)
C12—H120.9300C29—H290.9300
C13—C141.378 (3)C31—H31A0.9600
C13—H130.9300C31—H31B0.9600
C14—C151.391 (3)C31—H31C0.9600
C31—N1—C5113.8 (2)C10—C15—C6123.46 (18)
C31—N1—C2116.2 (2)O32—C16—C14126.81 (19)
C5—N1—C2106.7 (1)O32—C16—C2125.09 (18)
N1—C2—C6111.17 (15)C14—C16—C2108.05 (16)
N1—C2—C16113.49 (15)O33—C17—C18120.04 (17)
C6—C2—C16101.55 (13)O33—C17—C3121.28 (15)
N1—C2—C3102.31 (13)C18—C17—C3118.66 (15)
C6—C2—C3118.07 (14)C19—C18—C23120.45 (19)
C16—C2—C3110.72 (14)C19—C18—C17118.14 (19)
C25—C3—C17107.67 (14)C23—C18—C17121.32 (18)
C25—C3—C4113.56 (14)C20—C19—C18120.3 (3)
C17—C3—C4109.10 (14)C20—C19—H19119.9
C25—C3—C2115.27 (14)C18—C19—H19119.9
C17—C3—C2108.05 (13)C21—C20—C19119.3 (3)
C4—C3—C2102.95 (13)C21—C20—H20120.3
C26—C4—C5113.60 (15)C19—C20—H20120.3
C26—C4—C3117.45 (16)C22—C21—C20120.7 (2)
C5—C4—C3105.49 (13)C22—C21—H21119.7
C26—C4—H4106.5C20—C21—H21119.7
C5—C4—H4106.5C21—C22—C23121.8 (3)
C3—C4—H4106.5C21—C22—H22119.1
N1—C5—C4103.51 (15)C23—C22—H22119.1
N1—C5—H5A111.1C18—C23—C22117.4 (2)
C4—C5—H5A111.1C18—C23—C24121.05 (17)
N1—C5—H5B111.1C22—C23—C24121.5 (2)
C4—C5—H5B111.1C23—C24—C25113.16 (17)
H5A—C5—H5B109.0C23—C24—H24A108.9
C7—C6—C15118.37 (17)C25—C24—H24A108.9
C7—C6—C2132.16 (16)C23—C24—H24B108.9
C15—C6—C2109.39 (15)C25—C24—H24B108.9
C6—C7—C8119.32 (19)H24A—C24—H24B107.8
C6—C7—H7120.3C24—C25—C3114.08 (16)
C8—C7—H7120.3C24—C25—H25A108.7
C9—C8—C7122.1 (2)C3—C25—H25A108.7
C9—C8—H8118.9C24—C25—H25B108.7
C7—C8—H8118.9C3—C25—H25B108.7
C8—C9—C10120.33 (19)H25A—C25—H25B107.6
C8—C9—H9119.8C27—C26—O30110.17 (18)
C10—C9—H9119.8C27—C26—C4126.45 (18)
C15—C10—C9116.29 (18)O30—C26—C4123.29 (17)
C15—C10—C11115.7 (2)C26—C27—C28107.7 (2)
C9—C10—C11128.0 (2)C26—C27—H27126.2
C12—C11—C10121.2 (2)C28—C27—H27126.2
C12—C11—H11119.4C29—C28—C27107.2 (2)
C10—C11—H11119.4C29—C28—H28126.4
C11—C12—C13123.0 (2)C27—C28—H28126.4
C11—C12—H12118.5C28—C29—O30109.9 (2)
C13—C12—H12118.5C28—C29—H29125.0
C14—C13—C12116.9 (2)O30—C29—H29125.0
C14—C13—H13121.6C26—O30—C29105.05 (18)
C12—C13—H13121.6N1—C31—H31A109.5
C13—C14—C15120.04 (19)N1—C31—H31B109.5
C13—C14—C16132.4 (2)H31A—C31—H31B109.5
C15—C14—C16107.51 (16)N1—C31—H31C109.5
C14—C15—C10123.13 (17)H31A—C31—H31C109.5
C14—C15—C6113.39 (16)H31B—C31—H31C109.5
C31—N1—C2—C662.7 (2)C2—C6—C15—C142.3 (2)
C5—N1—C2—C6169.12 (15)C7—C6—C15—C103.3 (3)
C31—N1—C2—C1651.0 (2)C2—C6—C15—C10179.59 (16)
C5—N1—C2—C1677.15 (19)C13—C14—C16—O324.2 (4)
C31—N1—C2—C3170.34 (18)C15—C14—C16—O32175.8 (2)
C5—N1—C2—C342.17 (18)C13—C14—C16—C2178.2 (2)
N1—C2—C3—C25147.57 (16)C15—C14—C16—C21.8 (2)
C6—C2—C3—C2590.06 (19)N1—C2—C16—O3255.3 (3)
C16—C2—C3—C2526.3 (2)C6—C2—C16—O32174.7 (2)
N1—C2—C3—C1791.98 (16)C3—C2—C16—O3259.1 (3)
C6—C2—C3—C1730.4 (2)N1—C2—C16—C14122.35 (16)
C16—C2—C3—C17146.78 (15)C6—C2—C16—C142.96 (19)
N1—C2—C3—C423.37 (17)C3—C2—C16—C14123.26 (16)
C6—C2—C3—C4145.74 (15)C25—C3—C17—O33146.39 (17)
C16—C2—C3—C497.88 (16)C4—C3—C17—O3322.7 (2)
C25—C3—C4—C264.2 (2)C2—C3—C17—O3388.50 (19)
C17—C3—C4—C26115.93 (16)C25—C3—C17—C1835.11 (19)
C2—C3—C4—C26129.48 (16)C4—C3—C17—C18158.77 (15)
C25—C3—C4—C5123.58 (17)C2—C3—C17—C1889.99 (17)
C17—C3—C4—C5116.32 (16)O33—C17—C18—C197.3 (3)
C2—C3—C4—C51.73 (18)C3—C17—C18—C19171.23 (16)
C31—N1—C5—C4173.55 (18)O33—C17—C18—C23176.03 (17)
C2—N1—C5—C444.0 (2)C3—C17—C18—C235.5 (2)
C26—C4—C5—N1156.49 (16)C23—C18—C19—C202.1 (3)
C3—C4—C5—N126.5 (2)C17—C18—C19—C20174.60 (19)
N1—C2—C6—C752.4 (3)C18—C19—C20—C210.3 (4)
C16—C2—C6—C7173.4 (2)C19—C20—C21—C221.3 (4)
C3—C2—C6—C765.3 (3)C20—C21—C22—C231.1 (4)
N1—C2—C6—C15124.17 (16)C19—C18—C23—C222.2 (3)
C16—C2—C6—C153.14 (18)C17—C18—C23—C22174.39 (17)
C3—C2—C6—C15118.08 (16)C19—C18—C23—C24177.62 (17)
C15—C6—C7—C82.8 (3)C17—C18—C23—C245.8 (3)
C2—C6—C7—C8179.13 (19)C21—C22—C23—C180.6 (3)
C6—C7—C8—C90.5 (3)C21—C22—C23—C24179.2 (2)
C7—C8—C9—C101.5 (4)C18—C23—C24—C2515.1 (3)
C8—C9—C10—C151.0 (3)C22—C23—C24—C25164.74 (18)
C8—C9—C10—C11177.9 (2)C23—C24—C25—C347.8 (2)
C15—C10—C11—C121.9 (3)C17—C3—C25—C2456.3 (2)
C9—C10—C11—C12177.0 (2)C4—C3—C25—C24177.21 (16)
C10—C11—C12—C130.5 (4)C2—C3—C25—C2464.4 (2)
C11—C12—C13—C140.4 (4)C5—C4—C26—C27130.4 (2)
C12—C13—C14—C150.1 (3)C3—C4—C26—C27105.9 (2)
C12—C13—C14—C16179.9 (2)C5—C4—C26—O3045.9 (3)
C13—C14—C15—C101.7 (3)C3—C4—C26—O3077.8 (2)
C16—C14—C15—C10178.37 (17)O30—C26—C27—C280.5 (3)
C13—C14—C15—C6179.73 (17)C4—C26—C27—C28176.1 (2)
C16—C14—C15—C60.3 (2)C26—C27—C28—C290.9 (3)
C9—C10—C15—C14176.56 (18)C27—C28—C29—O300.8 (3)
C11—C10—C15—C142.5 (3)C27—C26—O30—C290.1 (2)
C9—C10—C15—C61.3 (3)C4—C26—O30—C29176.75 (19)
C11—C10—C15—C6179.60 (17)C28—C29—O30—C260.5 (3)
C7—C6—C15—C14174.79 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4···O330.982.212.762 (2)114
C5—H5B···O320.972.513.071 (3)117
C25—H25A···O320.972.483.141 (3)126
C29—H29···O33i0.932.523.417 (3)163
C28—H28···O32ii0.932.583.217 (4)126
C8—H8···O33iii0.932.523.392 (3)156
Symmetry codes: (i) x+2, y+1/2, z+1/2; (ii) x+2, y1/2, z+1/2; (iii) x+1, y+1, z.
 

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