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In the title compound, C25H18N2O4, the heterocyclic ring of the indole moiety is slightly distorted towards an envelope conformation. The oxetane plane is almost perpendicular to the indole plane and the dihedral angle between the oxetane and oxazole rings is 65.6 (2)°. The molecular structure is stabilized by C—H...O interactions and the crystal packing is stabilized by intermolecular C—H...O hydrogen bonds as well as dipole–dipole and van der Waals interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803024644/ci6294sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803024644/ci6294Isup2.hkl
Contains datablock I

CCDC reference: 227861

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.060
  • wR factor = 0.136
  • Data-to-parameter ratio = 10.6

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.51 Ratio PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.39 Ratio
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C18 PLAT320_ALERT_2_C Check Hybridisation of C2 in Main Residue . ?
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 3 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 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: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; 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, PARST (Nardelli, 1995) and PLATON (Spek, 1990).

1-Acetyl-4',5a'-diphenyl-2',2a',5',5a'-tetrahydrospiro[1H-indole-3,2'- oxeto[5,4-b]oxazol]-2(3H)-one top
Crystal data top
C25H18N2O4F(000) = 856
Mr = 410.41Dx = 1.339 Mg m3
Monoclinic, P21/cMelting point: 491–493 K K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 16.1912 (10) ÅCell parameters from 4012 reflections
b = 10.3984 (6) Åθ = 2.4–26.8°
c = 12.6742 (8) ŵ = 0.09 mm1
β = 107.432 (1)°T = 293 K
V = 2035.9 (2) Å3Plate, colourless
Z = 40.40 × 0.30 × 0.10 mm
Data collection top
Siemens SMART CCD area-detector
diffractometer
3567 independent reflections
Radiation source: fine-focus sealed tube2683 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
Detector resolution: 8.33 pixels mm-1θmax = 25.0°, θmin = 2.4°
ω scansh = 1919
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 1112
Tmin = 0.964, Tmax = 0.991l = 1510
9901 measured reflections
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)] = 0.060Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136H atoms treated by a mixture of independent and constrained refinement
S = 1.17 w = 1/[σ2(Fo2) + (0.0494P)2 + 0.7969P]
where P = (Fo2 + 2Fc2)/3
3567 reflections(Δ/σ)max = 0.001
337 parametersΔρmax = 0.16 e Å3
0 restraintsΔρmin = 0.23 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
O10.66990 (9)1.01001 (15)0.60090 (14)0.0437 (4)
O20.78606 (10)1.05041 (16)0.52549 (13)0.0470 (5)
O30.79986 (11)0.77676 (18)0.55875 (16)0.0566 (5)
O41.05555 (13)0.68101 (19)0.59529 (16)0.0639 (6)
N10.77576 (12)0.9336 (2)0.74877 (16)0.0427 (5)
N20.94860 (12)0.81393 (18)0.60713 (15)0.0396 (5)
C10.69765 (15)0.9256 (2)0.6880 (2)0.0391 (6)
C20.74349 (15)1.0906 (2)0.6032 (2)0.0417 (6)
C30.81479 (15)1.0332 (2)0.7010 (2)0.0403 (6)
C40.85690 (14)0.9905 (2)0.61075 (19)0.0376 (6)
C50.94683 (15)1.0351 (2)0.62400 (18)0.0390 (6)
C60.98074 (18)1.1578 (3)0.6394 (2)0.0482 (7)
C71.0695 (2)1.1726 (3)0.6598 (2)0.0586 (8)
C81.1215 (2)1.0670 (4)0.6664 (2)0.0618 (9)
C91.08850 (17)0.9437 (3)0.6518 (2)0.0532 (7)
C100.99992 (15)0.9291 (2)0.62894 (18)0.0399 (6)
C110.86116 (15)0.8469 (2)0.58892 (19)0.0401 (6)
C120.98007 (18)0.6921 (3)0.58910 (19)0.0472 (6)
C130.9182 (2)0.5828 (3)0.5622 (3)0.0667 (8)
H13A0.94960.50390.56490.100*
H13B0.87880.59430.48940.100*
H13C0.88640.57950.61500.100*
C140.71735 (16)1.2276 (2)0.5917 (2)0.0514 (7)
C150.73969 (19)1.3089 (3)0.5185 (3)0.0642 (9)
C160.7142 (2)1.4362 (3)0.5099 (4)0.0891 (13)
C170.6686 (3)1.4833 (4)0.5759 (5)0.1175 (19)
C180.6471 (3)1.4049 (4)0.6488 (5)0.1315 (19)
H180.61601.43730.69390.158*
C190.6709 (3)1.2777 (3)0.6566 (4)0.0919 (13)
C200.63263 (15)0.8359 (2)0.7048 (2)0.0434 (6)
C210.55174 (18)0.8240 (3)0.6287 (3)0.0640 (8)
C220.4937 (2)0.7353 (4)0.6470 (4)0.0876 (12)
C230.5158 (2)0.6613 (4)0.7404 (4)0.0829 (11)
C240.5948 (2)0.6736 (3)0.8164 (3)0.0702 (9)
C250.6537 (2)0.7603 (3)0.7994 (3)0.0550 (7)
H30.8500 (14)1.091 (2)0.7540 (19)0.036 (6)*
H60.9435 (15)1.230 (2)0.635 (2)0.043 (7)*
H71.0923 (18)1.256 (3)0.671 (2)0.064 (8)*
H81.1824 (19)1.078 (3)0.685 (2)0.063 (8)*
H91.1233 (17)0.871 (3)0.656 (2)0.054 (8)*
H150.772 (2)1.274 (3)0.472 (3)0.080 (11)*
H160.728 (2)1.491 (4)0.456 (3)0.097 (12)*
H170.651 (3)1.569 (4)0.569 (3)0.124 (15)*
H190.660 (2)1.227 (3)0.708 (3)0.076 (10)*
H210.5394 (17)0.874 (3)0.565 (2)0.058 (8)*
H220.441 (2)0.734 (3)0.596 (3)0.091 (11)*
H230.473 (2)0.602 (3)0.755 (3)0.100 (11)*
H240.612 (2)0.619 (3)0.879 (3)0.083 (11)*
H250.7089 (19)0.775 (3)0.849 (2)0.065 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0336 (9)0.0437 (9)0.0488 (10)0.0012 (7)0.0047 (7)0.0036 (8)
O20.0434 (9)0.0601 (11)0.0357 (9)0.0102 (8)0.0091 (8)0.0029 (8)
O30.0451 (10)0.0582 (12)0.0638 (12)0.0102 (9)0.0122 (9)0.0138 (10)
O40.0564 (12)0.0750 (14)0.0594 (13)0.0269 (10)0.0160 (10)0.0061 (10)
N10.0363 (11)0.0568 (13)0.0357 (11)0.0000 (9)0.0116 (9)0.0012 (10)
N20.0373 (11)0.0480 (12)0.0335 (11)0.0018 (9)0.0109 (9)0.0001 (9)
C10.0382 (13)0.0407 (13)0.0377 (13)0.0051 (11)0.0106 (11)0.0033 (11)
C20.0347 (13)0.0457 (14)0.0442 (14)0.0008 (10)0.0108 (11)0.0019 (11)
C30.0349 (12)0.0489 (15)0.0354 (13)0.0044 (11)0.0083 (11)0.0073 (12)
C40.0319 (12)0.0456 (14)0.0325 (12)0.0013 (10)0.0056 (10)0.0011 (11)
C50.0409 (13)0.0491 (15)0.0278 (12)0.0052 (11)0.0113 (10)0.0004 (11)
C60.0587 (18)0.0504 (17)0.0390 (15)0.0129 (14)0.0197 (13)0.0028 (12)
C70.069 (2)0.073 (2)0.0377 (15)0.0356 (18)0.0222 (14)0.0085 (14)
C80.0437 (17)0.102 (3)0.0417 (16)0.0234 (18)0.0165 (13)0.0064 (16)
C90.0385 (15)0.078 (2)0.0435 (16)0.0007 (15)0.0131 (12)0.0005 (15)
C100.0388 (13)0.0573 (15)0.0243 (12)0.0036 (11)0.0104 (10)0.0002 (11)
C110.0376 (13)0.0510 (15)0.0307 (13)0.0021 (12)0.0088 (11)0.0027 (11)
C120.0581 (17)0.0553 (16)0.0293 (13)0.0168 (13)0.0146 (12)0.0066 (12)
C130.093 (2)0.0509 (17)0.065 (2)0.0014 (16)0.0376 (18)0.0075 (15)
C140.0424 (14)0.0444 (15)0.0675 (18)0.0013 (12)0.0164 (13)0.0006 (14)
C150.0486 (17)0.0560 (19)0.083 (2)0.0044 (14)0.0121 (16)0.0133 (17)
C160.070 (2)0.053 (2)0.132 (4)0.0113 (18)0.011 (2)0.025 (2)
C170.108 (3)0.041 (2)0.197 (6)0.009 (2)0.036 (4)0.005 (3)
C180.173 (5)0.060 (3)0.194 (5)0.030 (3)0.104 (4)0.010 (3)
C190.122 (3)0.055 (2)0.123 (3)0.013 (2)0.073 (3)0.003 (2)
C200.0374 (13)0.0429 (14)0.0517 (16)0.0036 (11)0.0163 (12)0.0041 (12)
C210.0455 (16)0.068 (2)0.072 (2)0.0073 (14)0.0086 (15)0.0118 (17)
C220.0433 (18)0.090 (3)0.119 (3)0.0148 (18)0.009 (2)0.014 (2)
C230.064 (2)0.071 (2)0.127 (3)0.0081 (18)0.048 (2)0.018 (2)
C240.077 (2)0.062 (2)0.084 (2)0.0035 (17)0.043 (2)0.0172 (19)
C250.0551 (17)0.0572 (18)0.0549 (18)0.0002 (14)0.0199 (15)0.0047 (14)
Geometric parameters (Å, º) top
O1—C11.376 (3)C9—H90.93 (3)
O1—C21.450 (3)C12—C131.485 (4)
O2—C21.423 (3)C13—H13A0.96
O2—C41.459 (3)C13—H13B0.96
O3—C111.198 (3)C13—H13C0.96
O4—C121.207 (3)C14—C191.372 (4)
N1—C11.271 (3)C14—C151.381 (4)
N1—C31.438 (3)C15—C161.382 (5)
N2—C111.407 (3)C15—H150.97 (3)
N2—C121.409 (3)C16—C171.361 (6)
N2—C101.436 (3)C16—H160.96 (4)
C1—C201.470 (3)C17—C181.354 (7)
C2—C141.481 (4)C17—H170.93 (4)
C2—C31.539 (3)C18—C191.373 (5)
C3—C41.561 (3)C18—H180.93
C3—H30.95 (2)C19—H190.90 (3)
C4—C51.489 (3)C20—C211.380 (4)
C4—C111.524 (3)C20—C251.387 (4)
C5—C61.379 (3)C21—C221.385 (5)
C5—C101.388 (3)C21—H210.94 (3)
C6—C71.390 (4)C22—C231.367 (5)
C6—H60.95 (2)C22—H220.90 (3)
C7—C81.371 (4)C23—C241.357 (5)
C7—H70.94 (3)C23—H230.98 (4)
C8—C91.381 (4)C24—C251.376 (4)
C8—H80.95 (3)C24—H240.95 (3)
C9—C101.384 (3)C25—H250.94 (3)
C1—O1—C2106.49 (17)N2—C11—C4107.86 (19)
C2—O2—C492.82 (16)O4—C12—N2118.9 (3)
C1—N1—C3105.93 (19)O4—C12—C13122.8 (2)
C11—N2—C12125.9 (2)N2—C12—C13118.3 (2)
C11—N2—C10108.93 (19)C12—C13—H13A109.5
C12—N2—C10124.3 (2)C12—C13—H13B109.5
N1—C1—O1118.1 (2)H13A—C13—H13B109.5
N1—C1—C20125.4 (2)C12—C13—H13C109.5
O1—C1—C20116.5 (2)H13A—C13—H13C109.5
O2—C2—O1112.43 (19)H13B—C13—H13C109.5
O2—C2—C14113.5 (2)C19—C14—C15118.1 (3)
O1—C2—C14110.19 (19)C19—C14—C2119.9 (3)
O2—C2—C392.36 (17)C15—C14—C2122.0 (3)
O1—C2—C3101.85 (19)C14—C15—C16120.5 (4)
C14—C2—C3125.2 (2)C14—C15—H15118.7 (19)
N1—C3—C2107.49 (19)C16—C15—H15121 (2)
N1—C3—C4116.6 (2)C17—C16—C15120.0 (4)
C2—C3—C484.69 (17)C17—C16—H16120 (2)
N1—C3—H3113.7 (13)C15—C16—H16120 (2)
C2—C3—H3118.1 (13)C18—C17—C16120.0 (4)
C4—C3—H3113.2 (13)C18—C17—H17120 (3)
O2—C4—C5118.40 (19)C16—C17—H17120 (3)
O2—C4—C11110.62 (18)C17—C18—C19120.3 (5)
C5—C4—C11103.30 (19)C17—C18—H18119.9
O2—C4—C390.12 (16)C19—C18—H18119.9
C5—C4—C3117.12 (19)C14—C19—C18121.1 (4)
C11—C4—C3117.7 (2)C14—C19—H19119 (2)
C6—C5—C10120.9 (2)C18—C19—H19120 (2)
C6—C5—C4129.7 (2)C21—C20—C25119.3 (3)
C10—C5—C4109.2 (2)C21—C20—C1121.8 (2)
C5—C6—C7118.3 (3)C25—C20—C1118.9 (2)
C5—C6—H6120.0 (14)C20—C21—C22119.5 (3)
C7—C6—H6121.7 (14)C20—C21—H21117.9 (17)
C8—C7—C6120.4 (3)C22—C21—H21122.5 (17)
C8—C7—H7121.8 (17)C23—C22—C21120.4 (4)
C6—C7—H7117.8 (17)C23—C22—H22124 (2)
C7—C8—C9121.9 (3)C21—C22—H22116 (2)
C7—C8—H8119.2 (17)C24—C23—C22120.5 (3)
C9—C8—H8118.8 (17)C24—C23—H23120 (2)
C8—C9—C10117.7 (3)C22—C23—H23120 (2)
C8—C9—H9122.6 (16)C23—C24—C25120.1 (3)
C10—C9—H9119.6 (16)C23—C24—H24121 (2)
C9—C10—C5120.8 (2)C25—C24—H24118 (2)
C9—C10—N2129.4 (2)C24—C25—C20120.3 (3)
C5—C10—N2109.8 (2)C24—C25—H25124.5 (18)
O3—C11—N2126.9 (2)C20—C25—H25115.3 (18)
O3—C11—C4125.2 (2)
C3—N1—C1—O12.4 (3)C11—N2—C10—C9179.7 (2)
C3—N1—C1—C20179.8 (2)C12—N2—C10—C99.9 (4)
C2—O1—C1—N10.0 (3)C11—N2—C10—C50.5 (3)
C2—O1—C1—C20178.1 (2)C12—N2—C10—C5169.9 (2)
C4—O2—C2—O1103.03 (19)C12—N2—C11—O32.5 (4)
C4—O2—C2—C14131.1 (2)C10—N2—C11—O3172.7 (2)
C4—O2—C2—C30.82 (18)C12—N2—C11—C4175.6 (2)
C1—O1—C2—O299.7 (2)C10—N2—C11—C45.4 (2)
C1—O1—C2—C14132.6 (2)O2—C4—C11—O341.7 (3)
C1—O1—C2—C32.1 (2)C5—C4—C11—O3169.3 (2)
C1—N1—C3—C23.6 (3)C3—C4—C11—O359.9 (3)
C1—N1—C3—C489.2 (2)O2—C4—C11—N2136.54 (18)
O2—C2—C3—N1116.99 (19)C5—C4—C11—N28.9 (2)
O1—C2—C3—N13.5 (2)C3—C4—C11—N2121.9 (2)
C14—C2—C3—N1121.9 (3)C11—N2—C12—O4171.1 (2)
O2—C2—C3—C40.77 (17)C10—N2—C12—O42.3 (3)
O1—C2—C3—C4112.74 (18)C11—N2—C12—C138.4 (3)
C14—C2—C3—C4121.9 (3)C10—N2—C12—C13177.2 (2)
C2—O2—C4—C5122.1 (2)O2—C2—C14—C19176.0 (3)
C2—O2—C4—C11119.0 (2)O1—C2—C14—C1948.9 (4)
C2—O2—C4—C30.81 (18)C3—C2—C14—C1972.9 (4)
N1—C3—C4—O2107.7 (2)O2—C2—C14—C155.3 (3)
C2—C3—C4—O20.75 (17)O1—C2—C14—C15132.4 (3)
N1—C3—C4—C5130.0 (2)C3—C2—C14—C15105.8 (3)
C2—C3—C4—C5123.1 (2)C19—C14—C15—C161.3 (5)
N1—C3—C4—C115.8 (3)C2—C14—C15—C16180.0 (3)
C2—C3—C4—C11112.8 (2)C14—C15—C16—C171.7 (6)
O2—C4—C5—C653.5 (3)C15—C16—C17—C181.0 (7)
C11—C4—C5—C6176.2 (2)C16—C17—C18—C190.1 (8)
C3—C4—C5—C652.7 (3)C15—C14—C19—C180.2 (6)
O2—C4—C5—C10131.9 (2)C2—C14—C19—C18178.9 (4)
C11—C4—C5—C109.3 (2)C17—C18—C19—C140.5 (8)
C3—C4—C5—C10121.8 (2)N1—C1—C20—C21173.2 (3)
C10—C5—C6—C70.2 (4)O1—C1—C20—C219.0 (3)
C4—C5—C6—C7174.1 (2)N1—C1—C20—C256.2 (4)
C5—C6—C7—C81.3 (4)O1—C1—C20—C25171.6 (2)
C6—C7—C8—C90.9 (4)C25—C20—C21—C221.2 (5)
C7—C8—C9—C100.6 (4)C1—C20—C21—C22178.2 (3)
C8—C9—C10—C51.7 (4)C20—C21—C22—C230.9 (6)
C8—C9—C10—N2178.0 (2)C21—C22—C23—C240.0 (6)
C6—C5—C10—C91.4 (4)C22—C23—C24—C250.5 (6)
C4—C5—C10—C9173.7 (2)C23—C24—C25—C200.1 (5)
C6—C5—C10—N2178.4 (2)C21—C20—C25—C240.7 (4)
C4—C5—C10—N26.5 (3)C1—C20—C25—C24178.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···O4i0.95 (2)2.26 (2)3.192 (3)165 (2)
C9—H9···O40.93 (3)2.28 (3)2.834 (4)117 (2)
C15—H15···O20.97 (3)2.41 (3)2.785 (4)102 (2)
C21—H21···O10.93 (3)2.47 (3)2.816 (4)102 (2)
C25—H25···N10.94 (3)2.52 (3)2.885 (4)104 (2)
Symmetry code: (i) x+2, y+1/2, z+3/2.
 

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