The title compound, C
20H
15N
3O
2·0.5CH
3OH, has been synthesized from the ene-lactam with P(OEt)
3 under an N
2 atmosphere. The title indole molecules are linked
via N—H
O hydrogen bonds, forming one-dimensional chains.
Supporting information
CCDC reference: 245341
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
No syntax errors found
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
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-2
H-
oxazolo[4',5':5,6]pyrido[3,4-
b]indole methanol hemisolvate
top
Crystal data top
C20H15N3O2·0.5CH4O | F(000) = 1448 |
Mr = 345.37 | Dx = 1.402 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 883 reflections |
a = 17.728 (4) Å | θ = 2.4–22.7° |
b = 8.5045 (19) Å | µ = 0.09 mm−1 |
c = 22.575 (5) Å | T = 293 K |
β = 105.925 (4)° | Block, colourless |
V = 3273.0 (12) Å3 | 0.3 × 0.2 × 0.2 mm |
Z = 8 | |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 2884 independent reflections |
Radiation source: sealed tube | 2232 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.071 |
φ and ω scans | θmax = 25.0°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −17→20 |
Tmin = 0.97, Tmax = 0.98 | k = −10→9 |
7860 measured reflections | l = −26→18 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.147 | H-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 parameters | Δρmax = 0.28 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−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. 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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
C2 | 0.05791 (12) | −0.1542 (3) | 0.47163 (11) | 0.0613 (6) | |
C5 | 0.23704 (11) | 0.1080 (2) | 0.40628 (9) | 0.0428 (5) | |
C7 | 0.45438 (12) | 0.0945 (3) | 0.59654 (10) | 0.0560 (6) | |
H7 | 0.4921 | 0.1612 | 0.5887 | 0.067* | |
C8 | 0.46728 (12) | 0.0166 (3) | 0.65127 (10) | 0.0616 (6) | |
H8 | 0.5147 | 0.0302 | 0.6813 | 0.074* | |
C9 | 0.41084 (13) | −0.0828 (3) | 0.66295 (11) | 0.0605 (6) | |
H9 | 0.4219 | −0.1375 | 0.7000 | 0.073* | |
C10 | 0.33970 (12) | −0.1017 (3) | 0.62118 (10) | 0.0525 (5) | |
H10 | 0.3019 | −0.1659 | 0.6302 | 0.063* | |
C11 | 0.13411 (15) | −0.1204 (3) | 0.61983 (13) | 0.0753 (7) | |
H11A | 0.1709 | −0.0357 | 0.6235 | 0.113* | |
H11B | 0.1432 | −0.1735 | 0.6587 | 0.113* | |
H11C | 0.0817 | −0.0792 | 0.6080 | 0.113* | |
C12 | 0.14410 (12) | −0.2319 (3) | 0.57283 (11) | 0.0599 (6) | |
H12A | 0.1077 | −0.3187 | 0.5696 | 0.072* | |
H12B | 0.1970 | −0.2741 | 0.5848 | 0.072* | |
C13 | 0.26387 (11) | 0.1905 (2) | 0.35818 (9) | 0.0443 (5) | |
C14 | 0.21032 (13) | 0.2764 (3) | 0.31347 (10) | 0.0556 (6) | |
H14 | 0.1584 | 0.2830 | 0.3147 | 0.067* | |
C15 | 0.23331 (16) | 0.3520 (3) | 0.26731 (11) | 0.0659 (6) | |
H15 | 0.1967 | 0.4088 | 0.2376 | 0.079* | |
C16 | 0.30952 (15) | 0.3444 (3) | 0.26464 (11) | 0.0646 (6) | |
H16 | 0.3248 | 0.3961 | 0.2335 | 0.077* | |
C17 | 0.36293 (14) | 0.2601 (3) | 0.30833 (11) | 0.0600 (6) | |
H17 | 0.4147 | 0.2547 | 0.3067 | 0.072* | |
C18 | 0.34110 (12) | 0.1829 (2) | 0.35484 (10) | 0.0496 (5) | |
H18 | 0.3781 | 0.1256 | 0.3841 | 0.060* | |
C3A | 0.13925 (11) | −0.0207 (2) | 0.43145 (9) | 0.0480 (5) | |
C5A | 0.28338 (10) | 0.0794 (2) | 0.46650 (9) | 0.0401 (5) | |
C6A | 0.38305 (10) | 0.0706 (2) | 0.55298 (9) | 0.0441 (5) | |
C10A | 0.32386 (10) | −0.0235 (2) | 0.56451 (9) | 0.0420 (5) | |
C10B | 0.25849 (10) | −0.0140 (2) | 0.50990 (9) | 0.0401 (4) | |
C10C | 0.18072 (11) | −0.0647 (2) | 0.48938 (9) | 0.0451 (5) | |
N1 | 0.12976 (10) | −0.1528 (2) | 0.51291 (8) | 0.0546 (5) | |
N4 | 0.16202 (9) | 0.0569 (2) | 0.38948 (8) | 0.0485 (4) | |
N6 | 0.35864 (9) | 0.1299 (2) | 0.49417 (7) | 0.0460 (4) | |
H6 | 0.3861 | 0.1893 | 0.4773 | 0.055* | |
O1 | −0.00186 (9) | −0.2114 (2) | 0.47665 (8) | 0.0847 (6) | |
O3 | 0.06267 (8) | −0.07450 (19) | 0.41982 (7) | 0.0608 (4) | |
C19 | 0.0000 | 0.0843 (8) | 0.2500 | 0.140 (2) | |
H19A | −0.0077 | 0.0780 | 0.2063 | 0.210* | 0.50 |
H19B | −0.0493 | 0.1045 | 0.2584 | 0.210* | 0.50 |
H19C | 0.0360 | 0.1680 | 0.2666 | 0.210* | 0.50 |
O4 | 0.0294 (4) | −0.0473 (9) | 0.2749 (2) | 0.156 (2) | 0.50 |
H4C | 0.0367 | −0.0447 | 0.3137 | 0.188* | 0.50 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C2 | 0.0464 (13) | 0.0796 (16) | 0.0585 (14) | −0.0205 (11) | 0.0153 (11) | −0.0045 (12) |
C5 | 0.0435 (11) | 0.0402 (11) | 0.0439 (11) | −0.0009 (8) | 0.0108 (9) | −0.0042 (8) |
C7 | 0.0348 (11) | 0.0752 (15) | 0.0566 (14) | −0.0069 (10) | 0.0099 (10) | 0.0007 (11) |
C8 | 0.0400 (12) | 0.0867 (17) | 0.0531 (14) | 0.0020 (11) | 0.0045 (10) | 0.0022 (12) |
C9 | 0.0497 (13) | 0.0809 (17) | 0.0480 (13) | 0.0054 (11) | 0.0084 (10) | 0.0113 (11) |
C10 | 0.0482 (12) | 0.0606 (13) | 0.0502 (13) | −0.0017 (9) | 0.0162 (10) | 0.0082 (10) |
C11 | 0.0723 (16) | 0.0778 (17) | 0.0777 (18) | 0.0071 (13) | 0.0235 (14) | −0.0053 (14) |
C12 | 0.0512 (13) | 0.0590 (14) | 0.0733 (16) | −0.0083 (10) | 0.0236 (11) | −0.0036 (12) |
C13 | 0.0494 (11) | 0.0410 (11) | 0.0414 (11) | −0.0038 (8) | 0.0107 (9) | −0.0039 (9) |
C14 | 0.0577 (13) | 0.0541 (13) | 0.0520 (13) | −0.0023 (10) | 0.0099 (10) | 0.0000 (11) |
C15 | 0.0833 (17) | 0.0618 (15) | 0.0463 (13) | 0.0017 (12) | 0.0072 (12) | 0.0091 (11) |
C16 | 0.0886 (18) | 0.0596 (14) | 0.0515 (14) | −0.0048 (12) | 0.0294 (13) | 0.0054 (11) |
C17 | 0.0717 (14) | 0.0615 (14) | 0.0554 (14) | −0.0026 (11) | 0.0317 (12) | −0.0023 (11) |
C18 | 0.0556 (12) | 0.0491 (12) | 0.0464 (12) | 0.0010 (9) | 0.0178 (10) | −0.0013 (9) |
C3A | 0.0365 (11) | 0.0581 (13) | 0.0470 (12) | −0.0098 (9) | 0.0076 (9) | −0.0081 (10) |
C5A | 0.0367 (10) | 0.0407 (10) | 0.0437 (11) | −0.0029 (7) | 0.0122 (8) | −0.0044 (8) |
C6A | 0.0373 (10) | 0.0514 (11) | 0.0443 (11) | −0.0007 (8) | 0.0124 (8) | −0.0012 (9) |
C10A | 0.0349 (10) | 0.0473 (11) | 0.0445 (11) | −0.0006 (8) | 0.0121 (8) | −0.0024 (9) |
C10B | 0.0370 (10) | 0.0424 (10) | 0.0419 (11) | −0.0024 (8) | 0.0126 (8) | −0.0025 (9) |
C10C | 0.0399 (11) | 0.0498 (12) | 0.0465 (12) | −0.0067 (8) | 0.0136 (9) | −0.0047 (9) |
N1 | 0.0432 (10) | 0.0696 (12) | 0.0520 (11) | −0.0177 (8) | 0.0145 (8) | 0.0008 (9) |
N4 | 0.0418 (9) | 0.0554 (10) | 0.0462 (10) | −0.0051 (7) | 0.0085 (8) | −0.0028 (8) |
N6 | 0.0381 (9) | 0.0549 (10) | 0.0451 (10) | −0.0106 (7) | 0.0117 (7) | 0.0025 (8) |
O1 | 0.0489 (9) | 0.1241 (16) | 0.0802 (12) | −0.0388 (10) | 0.0160 (8) | −0.0013 (11) |
O3 | 0.0389 (8) | 0.0847 (11) | 0.0554 (10) | −0.0166 (7) | 0.0072 (7) | −0.0016 (8) |
C19 | 0.092 (4) | 0.138 (5) | 0.145 (6) | 0.000 | −0.043 (3) | 0.000 |
O4 | 0.168 (6) | 0.209 (6) | 0.085 (4) | 0.041 (5) | 0.023 (3) | 0.010 (4) |
Geometric parameters (Å, º) top
C2—O1 | 1.199 (2) | C15—C16 | 1.370 (3) |
C2—N1 | 1.356 (3) | C15—H15 | 0.9300 |
C2—O3 | 1.374 (3) | C16—C17 | 1.368 (3) |
C5—N4 | 1.351 (2) | C16—H16 | 0.9300 |
C5—C5A | 1.403 (3) | C17—C18 | 1.381 (3) |
C5—C13 | 1.477 (3) | C17—H17 | 0.9300 |
C7—C8 | 1.365 (3) | C18—H18 | 0.9300 |
C7—C6A | 1.387 (3) | C3A—N4 | 1.306 (3) |
C7—H7 | 0.9300 | C3A—C10C | 1.365 (3) |
C8—C9 | 1.389 (3) | C3A—O3 | 1.388 (2) |
C8—H8 | 0.9300 | C5A—N6 | 1.377 (2) |
C9—C10 | 1.361 (3) | C5A—C10B | 1.423 (3) |
C9—H9 | 0.9300 | C6A—N6 | 1.375 (2) |
C10—C10A | 1.400 (3) | C6A—C10A | 1.400 (3) |
C10—H10 | 0.9300 | C10A—C10B | 1.444 (3) |
C11—C12 | 1.470 (3) | C10B—C10C | 1.397 (3) |
C11—H11A | 0.9600 | C10C—N1 | 1.387 (2) |
C11—H11B | 0.9600 | N6—H6 | 0.8600 |
C11—H11C | 0.9600 | C19—O4i | 1.296 (7) |
C12—N1 | 1.469 (3) | C19—O4 | 1.296 (7) |
C12—H12A | 0.9700 | C19—H19A | 0.9600 |
C12—H12B | 0.9700 | C19—H19B | 0.9601 |
C13—C14 | 1.389 (3) | C19—H19C | 0.9600 |
C13—C18 | 1.393 (3) | O4—O4i | 1.307 (11) |
C14—C15 | 1.378 (3) | O4—H4C | 0.8500 |
C14—H14 | 0.9300 | | |
| | | |
O1—C2—N1 | 128.8 (2) | C18—C17—H17 | 119.5 |
O1—C2—O3 | 122.9 (2) | C17—C18—C13 | 120.3 (2) |
N1—C2—O3 | 108.37 (17) | C17—C18—H18 | 119.9 |
N4—C5—C5A | 119.09 (18) | C13—C18—H18 | 119.9 |
N4—C5—C13 | 115.92 (18) | N4—C3A—C10C | 129.89 (18) |
C5A—C5—C13 | 124.99 (17) | N4—C3A—O3 | 120.70 (18) |
C8—C7—C6A | 117.65 (19) | C10C—C3A—O3 | 109.41 (18) |
C8—C7—H7 | 121.2 | N6—C5A—C5 | 128.48 (17) |
C6A—C7—H7 | 121.2 | N6—C5A—C10B | 107.87 (16) |
C7—C8—C9 | 121.1 (2) | C5—C5A—C10B | 123.64 (17) |
C7—C8—H8 | 119.4 | N6—C6A—C7 | 127.94 (18) |
C9—C8—H8 | 119.4 | N6—C6A—C10A | 109.65 (16) |
C10—C9—C8 | 121.3 (2) | C7—C6A—C10A | 122.42 (19) |
C10—C9—H9 | 119.4 | C10—C10A—C6A | 117.95 (17) |
C8—C9—H9 | 119.4 | C10—C10A—C10B | 136.01 (17) |
C9—C10—C10A | 119.51 (19) | C6A—C10A—C10B | 106.04 (16) |
C9—C10—H10 | 120.2 | C10C—C10B—C5A | 114.12 (17) |
C10A—C10—H10 | 120.2 | C10C—C10B—C10A | 138.92 (18) |
C12—C11—H11A | 109.5 | C5A—C10B—C10A | 106.93 (15) |
C12—C11—H11B | 109.5 | C3A—C10C—N1 | 106.20 (16) |
H11A—C11—H11B | 109.5 | C3A—C10C—C10B | 117.13 (18) |
C12—C11—H11C | 109.5 | N1—C10C—C10B | 136.66 (19) |
H11A—C11—H11C | 109.5 | C2—N1—C10C | 109.22 (18) |
H11B—C11—H11C | 109.5 | C2—N1—C12 | 121.43 (17) |
C11—C12—N1 | 110.2 (2) | C10C—N1—C12 | 129.32 (16) |
C11—C12—H12A | 109.6 | C3A—N4—C5 | 115.79 (17) |
N1—C12—H12A | 109.6 | C6A—N6—C5A | 109.43 (15) |
C11—C12—H12B | 109.6 | C6A—N6—H6 | 125.3 |
N1—C12—H12B | 109.6 | C5A—N6—H6 | 125.3 |
H12A—C12—H12B | 108.1 | C2—O3—C3A | 106.68 (16) |
C14—C13—C18 | 118.11 (19) | O4i—C19—O4 | 60.5 (6) |
C14—C13—C5 | 119.38 (18) | O4i—C19—H19A | 65.1 |
C18—C13—C5 | 122.50 (18) | O4—C19—H19A | 109.0 |
C15—C14—C13 | 120.7 (2) | O4i—C19—H19B | 87.8 |
C15—C14—H14 | 119.7 | O4—C19—H19B | 110.4 |
C13—C14—H14 | 119.7 | H19A—C19—H19B | 109.5 |
C16—C15—C14 | 120.7 (2) | O4i—C19—H19C | 162.5 |
C16—C15—H15 | 119.6 | O4—C19—H19C | 109.1 |
C14—C15—H15 | 119.6 | H19A—C19—H19C | 109.5 |
C17—C16—C15 | 119.3 (2) | H19B—C19—H19C | 109.5 |
C17—C16—H16 | 120.4 | C19—O4—O4i | 59.7 (3) |
C15—C16—H16 | 120.4 | C19—O4—H4C | 110.7 |
C16—C17—C18 | 121.0 (2) | O4i—O4—H4C | 138.4 |
C16—C17—H17 | 119.5 | | |
Symmetry code: (i) −x, y, −z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N6—H6···O1ii | 0.86 | 2.16 | 2.938 (2) | 150 |
Symmetry code: (ii) x+1/2, y+1/2, z. |