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The title compound, C20H15N3O2·0.5CH3OH, has been synthesized from the ene-lactam with P(OEt)3 under an N2 atmosphere. The title indole mol­ecules are linked via N—H...O hydrogen bonds, forming one-dimensional chains.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804015193/ob6377sup1.cif
Contains datablocks global, 2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804015193/ob63772sup2.hkl
Contains datablock 2

CCDC reference: 245341

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • Disorder in solvent or counterion
  • R factor = 0.052
  • wR factor = 0.147
  • Data-to-parameter ratio = 12.0

checkCIF/PLATON results

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Alert level C PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 33.00 Perc.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 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, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and Mercury (Version 1.2.1; Bruno et al., 2002); software used to prepare material for publication: SHELXTL.

1-Ethyl-2-oxo-5-phenyl-1,6-dihydro-2H- oxazolo[4',5':5,6]pyrido[3,4-b]indole methanol hemisolvate top
Crystal data top
C20H15N3O2·0.5CH4OF(000) = 1448
Mr = 345.37Dx = 1.402 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 883 reflections
a = 17.728 (4) Åθ = 2.4–22.7°
b = 8.5045 (19) ŵ = 0.09 mm1
c = 22.575 (5) ÅT = 293 K
β = 105.925 (4)°Block, colourless
V = 3273.0 (12) Å30.3 × 0.2 × 0.2 mm
Z = 8
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2884 independent reflections
Radiation source: sealed tube2232 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.071
φ and ω scansθmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1720
Tmin = 0.97, Tmax = 0.98k = 109
7860 measured reflectionsl = 2618
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) = 0.147H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.081P)2 + 0.3023P]
where P = (Fo2 + 2Fc2)/3
2884 reflections(Δ/σ)max = 0.011
241 parametersΔρmax = 0.28 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. The structure was solved by direct methods (Bruker, 2000) and successive difference Fourier syntheses. 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*/UeqOcc. (<1)
C20.05791 (12)0.1542 (3)0.47163 (11)0.0613 (6)
C50.23704 (11)0.1080 (2)0.40628 (9)0.0428 (5)
C70.45438 (12)0.0945 (3)0.59654 (10)0.0560 (6)
H70.49210.16120.58870.067*
C80.46728 (12)0.0166 (3)0.65127 (10)0.0616 (6)
H80.51470.03020.68130.074*
C90.41084 (13)0.0828 (3)0.66295 (11)0.0605 (6)
H90.42190.13750.70000.073*
C100.33970 (12)0.1017 (3)0.62118 (10)0.0525 (5)
H100.30190.16590.63020.063*
C110.13411 (15)0.1204 (3)0.61983 (13)0.0753 (7)
H11A0.17090.03570.62350.113*
H11B0.14320.17350.65870.113*
H11C0.08170.07920.60800.113*
C120.14410 (12)0.2319 (3)0.57283 (11)0.0599 (6)
H12A0.10770.31870.56960.072*
H12B0.19700.27410.58480.072*
C130.26387 (11)0.1905 (2)0.35818 (9)0.0443 (5)
C140.21032 (13)0.2764 (3)0.31347 (10)0.0556 (6)
H140.15840.28300.31470.067*
C150.23331 (16)0.3520 (3)0.26731 (11)0.0659 (6)
H150.19670.40880.23760.079*
C160.30952 (15)0.3444 (3)0.26464 (11)0.0646 (6)
H160.32480.39610.23350.077*
C170.36293 (14)0.2601 (3)0.30833 (11)0.0600 (6)
H170.41470.25470.30670.072*
C180.34110 (12)0.1829 (2)0.35484 (10)0.0496 (5)
H180.37810.12560.38410.060*
C3A0.13925 (11)0.0207 (2)0.43145 (9)0.0480 (5)
C5A0.28338 (10)0.0794 (2)0.46650 (9)0.0401 (5)
C6A0.38305 (10)0.0706 (2)0.55298 (9)0.0441 (5)
C10A0.32386 (10)0.0235 (2)0.56451 (9)0.0420 (5)
C10B0.25849 (10)0.0140 (2)0.50990 (9)0.0401 (4)
C10C0.18072 (11)0.0647 (2)0.48938 (9)0.0451 (5)
N10.12976 (10)0.1528 (2)0.51291 (8)0.0546 (5)
N40.16202 (9)0.0569 (2)0.38948 (8)0.0485 (4)
N60.35864 (9)0.1299 (2)0.49417 (7)0.0460 (4)
H60.38610.18930.47730.055*
O10.00186 (9)0.2114 (2)0.47665 (8)0.0847 (6)
O30.06267 (8)0.07450 (19)0.41982 (7)0.0608 (4)
C190.00000.0843 (8)0.25000.140 (2)
H19A0.00770.07800.20630.210*0.50
H19B0.04930.10450.25840.210*0.50
H19C0.03600.16800.26660.210*0.50
O40.0294 (4)0.0473 (9)0.2749 (2)0.156 (2)0.50
H4C0.03670.04470.31370.188*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C20.0464 (13)0.0796 (16)0.0585 (14)0.0205 (11)0.0153 (11)0.0045 (12)
C50.0435 (11)0.0402 (11)0.0439 (11)0.0009 (8)0.0108 (9)0.0042 (8)
C70.0348 (11)0.0752 (15)0.0566 (14)0.0069 (10)0.0099 (10)0.0007 (11)
C80.0400 (12)0.0867 (17)0.0531 (14)0.0020 (11)0.0045 (10)0.0022 (12)
C90.0497 (13)0.0809 (17)0.0480 (13)0.0054 (11)0.0084 (10)0.0113 (11)
C100.0482 (12)0.0606 (13)0.0502 (13)0.0017 (9)0.0162 (10)0.0082 (10)
C110.0723 (16)0.0778 (17)0.0777 (18)0.0071 (13)0.0235 (14)0.0053 (14)
C120.0512 (13)0.0590 (14)0.0733 (16)0.0083 (10)0.0236 (11)0.0036 (12)
C130.0494 (11)0.0410 (11)0.0414 (11)0.0038 (8)0.0107 (9)0.0039 (9)
C140.0577 (13)0.0541 (13)0.0520 (13)0.0023 (10)0.0099 (10)0.0000 (11)
C150.0833 (17)0.0618 (15)0.0463 (13)0.0017 (12)0.0072 (12)0.0091 (11)
C160.0886 (18)0.0596 (14)0.0515 (14)0.0048 (12)0.0294 (13)0.0054 (11)
C170.0717 (14)0.0615 (14)0.0554 (14)0.0026 (11)0.0317 (12)0.0023 (11)
C180.0556 (12)0.0491 (12)0.0464 (12)0.0010 (9)0.0178 (10)0.0013 (9)
C3A0.0365 (11)0.0581 (13)0.0470 (12)0.0098 (9)0.0076 (9)0.0081 (10)
C5A0.0367 (10)0.0407 (10)0.0437 (11)0.0029 (7)0.0122 (8)0.0044 (8)
C6A0.0373 (10)0.0514 (11)0.0443 (11)0.0007 (8)0.0124 (8)0.0012 (9)
C10A0.0349 (10)0.0473 (11)0.0445 (11)0.0006 (8)0.0121 (8)0.0024 (9)
C10B0.0370 (10)0.0424 (10)0.0419 (11)0.0024 (8)0.0126 (8)0.0025 (9)
C10C0.0399 (11)0.0498 (12)0.0465 (12)0.0067 (8)0.0136 (9)0.0047 (9)
N10.0432 (10)0.0696 (12)0.0520 (11)0.0177 (8)0.0145 (8)0.0008 (9)
N40.0418 (9)0.0554 (10)0.0462 (10)0.0051 (7)0.0085 (8)0.0028 (8)
N60.0381 (9)0.0549 (10)0.0451 (10)0.0106 (7)0.0117 (7)0.0025 (8)
O10.0489 (9)0.1241 (16)0.0802 (12)0.0388 (10)0.0160 (8)0.0013 (11)
O30.0389 (8)0.0847 (11)0.0554 (10)0.0166 (7)0.0072 (7)0.0016 (8)
C190.092 (4)0.138 (5)0.145 (6)0.0000.043 (3)0.000
O40.168 (6)0.209 (6)0.085 (4)0.041 (5)0.023 (3)0.010 (4)
Geometric parameters (Å, º) top
C2—O11.199 (2)C15—C161.370 (3)
C2—N11.356 (3)C15—H150.9300
C2—O31.374 (3)C16—C171.368 (3)
C5—N41.351 (2)C16—H160.9300
C5—C5A1.403 (3)C17—C181.381 (3)
C5—C131.477 (3)C17—H170.9300
C7—C81.365 (3)C18—H180.9300
C7—C6A1.387 (3)C3A—N41.306 (3)
C7—H70.9300C3A—C10C1.365 (3)
C8—C91.389 (3)C3A—O31.388 (2)
C8—H80.9300C5A—N61.377 (2)
C9—C101.361 (3)C5A—C10B1.423 (3)
C9—H90.9300C6A—N61.375 (2)
C10—C10A1.400 (3)C6A—C10A1.400 (3)
C10—H100.9300C10A—C10B1.444 (3)
C11—C121.470 (3)C10B—C10C1.397 (3)
C11—H11A0.9600C10C—N11.387 (2)
C11—H11B0.9600N6—H60.8600
C11—H11C0.9600C19—O4i1.296 (7)
C12—N11.469 (3)C19—O41.296 (7)
C12—H12A0.9700C19—H19A0.9600
C12—H12B0.9700C19—H19B0.9601
C13—C141.389 (3)C19—H19C0.9600
C13—C181.393 (3)O4—O4i1.307 (11)
C14—C151.378 (3)O4—H4C0.8500
C14—H140.9300
O1—C2—N1128.8 (2)C18—C17—H17119.5
O1—C2—O3122.9 (2)C17—C18—C13120.3 (2)
N1—C2—O3108.37 (17)C17—C18—H18119.9
N4—C5—C5A119.09 (18)C13—C18—H18119.9
N4—C5—C13115.92 (18)N4—C3A—C10C129.89 (18)
C5A—C5—C13124.99 (17)N4—C3A—O3120.70 (18)
C8—C7—C6A117.65 (19)C10C—C3A—O3109.41 (18)
C8—C7—H7121.2N6—C5A—C5128.48 (17)
C6A—C7—H7121.2N6—C5A—C10B107.87 (16)
C7—C8—C9121.1 (2)C5—C5A—C10B123.64 (17)
C7—C8—H8119.4N6—C6A—C7127.94 (18)
C9—C8—H8119.4N6—C6A—C10A109.65 (16)
C10—C9—C8121.3 (2)C7—C6A—C10A122.42 (19)
C10—C9—H9119.4C10—C10A—C6A117.95 (17)
C8—C9—H9119.4C10—C10A—C10B136.01 (17)
C9—C10—C10A119.51 (19)C6A—C10A—C10B106.04 (16)
C9—C10—H10120.2C10C—C10B—C5A114.12 (17)
C10A—C10—H10120.2C10C—C10B—C10A138.92 (18)
C12—C11—H11A109.5C5A—C10B—C10A106.93 (15)
C12—C11—H11B109.5C3A—C10C—N1106.20 (16)
H11A—C11—H11B109.5C3A—C10C—C10B117.13 (18)
C12—C11—H11C109.5N1—C10C—C10B136.66 (19)
H11A—C11—H11C109.5C2—N1—C10C109.22 (18)
H11B—C11—H11C109.5C2—N1—C12121.43 (17)
C11—C12—N1110.2 (2)C10C—N1—C12129.32 (16)
C11—C12—H12A109.6C3A—N4—C5115.79 (17)
N1—C12—H12A109.6C6A—N6—C5A109.43 (15)
C11—C12—H12B109.6C6A—N6—H6125.3
N1—C12—H12B109.6C5A—N6—H6125.3
H12A—C12—H12B108.1C2—O3—C3A106.68 (16)
C14—C13—C18118.11 (19)O4i—C19—O460.5 (6)
C14—C13—C5119.38 (18)O4i—C19—H19A65.1
C18—C13—C5122.50 (18)O4—C19—H19A109.0
C15—C14—C13120.7 (2)O4i—C19—H19B87.8
C15—C14—H14119.7O4—C19—H19B110.4
C13—C14—H14119.7H19A—C19—H19B109.5
C16—C15—C14120.7 (2)O4i—C19—H19C162.5
C16—C15—H15119.6O4—C19—H19C109.1
C14—C15—H15119.6H19A—C19—H19C109.5
C17—C16—C15119.3 (2)H19B—C19—H19C109.5
C17—C16—H16120.4C19—O4—O4i59.7 (3)
C15—C16—H16120.4C19—O4—H4C110.7
C16—C17—C18121.0 (2)O4i—O4—H4C138.4
C16—C17—H17119.5
Symmetry code: (i) x, y, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N6—H6···O1ii0.862.162.938 (2)150
Symmetry code: (ii) x+1/2, y+1/2, z.
 

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