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The title compound, C11H9NO, crystallizes with four independent mol­ecules in the asymmetric unit. The formyl group in each mol­ecule is coplanar with the attached quinoline ring system. The independent mol­ecules exist as two pseudo-inversion-related pairs. Each set of these mol­ecules forms sheets parallel to the ac plane which are alternately stacked along the b axis. The crystal packing is stabilized by C—H...O inter­molecular hydrogen-bonding inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680703574X/ci2423sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680703574X/ci2423Isup2.hkl
Contains datablock I

CCDC reference: 657841

Key indicators

  • Single-crystal X-ray study
  • T = 203 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.061
  • wR factor = 0.188
  • Data-to-parameter ratio = 25.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 43 Perc. PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.98 PLAT230_ALERT_2_C Hirshfeld Test Diff for C4C - C5C .. 5.68 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C7C - C8C .. 5.57 su PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C11C PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 24
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 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 2 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 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

Quinolines have been interesting to researchers for many years because a large number of natural products contain these heterocycles. They are found in numerous commercial products, including pharmaceuticals, fragrances and dyes. Quinoline alkaloids such as quinine, chloroquin, mefloquine and amodiaquine are used as efficient drugs for the treatment of malaria. Several quinoline derivatives have been evaluated in vitro against several parasites and HTLV-1 transformed cells. Prompted by the varied biological activities, the crystal structure of the title compound is reported.

The asymmetric unit of the title compound contains four independent molecules A, B, C and D; one of the independent molecules, A, is shown in Fig. 1. The N1—C1—C10—C11 torsion angles [(A) 1.7 (2)°, (B) 1.0 (2)°, (C) -1.0 (2)° and (D) 0.2 (2)°] indicate that the acetate group in each independent molecule is coplanar with the attached quinoline ring system.

The independent molecules exist as two pseudo inversion-related pairs (A/C and B/D). In the B/D pair the centroids of the pyridine rings are separated by a distance of 3.7181 (9) Å, indicating π-π stacking interaction. Crystal packing shows each set of these molecules form sheets parallel to the ac plane. One of the sheets is shown in Fig. 2. The sheets formed by the A/C and B/D pairs are alternately stacked along the b axis. The sheets are cross-linked by C—H···O intermolecular hydrogen-bonding interactions (Fig. 3).

Related literature top

For related structures, see: Lynch & McClenaghan (2001); Firley et al. (2005); Yathirajan et al. (2007). For related literature, see: Padwa et al. (1999); Robert & Meunier (1998); Franck et al. (2004).

Experimental top

The title compound was obtained as a gift sample from Sequent Scientific Ltd, Mangalore, India. The sample was crystallized from ethyl acetate (m.p. 325–327 K).

Refinement top

The H atoms were included in the riding model approximation with C—H = 0.94 or 0.97 Å, and with Uiso(H) = 1.18–1.50Ueq(C). A rotating group model was used for the methyl groups. Owing to the poor diffraction quality of the crystal, the ratio of observed to unique reflections is low (43%).

Structure description top

Quinolines have been interesting to researchers for many years because a large number of natural products contain these heterocycles. They are found in numerous commercial products, including pharmaceuticals, fragrances and dyes. Quinoline alkaloids such as quinine, chloroquin, mefloquine and amodiaquine are used as efficient drugs for the treatment of malaria. Several quinoline derivatives have been evaluated in vitro against several parasites and HTLV-1 transformed cells. Prompted by the varied biological activities, the crystal structure of the title compound is reported.

The asymmetric unit of the title compound contains four independent molecules A, B, C and D; one of the independent molecules, A, is shown in Fig. 1. The N1—C1—C10—C11 torsion angles [(A) 1.7 (2)°, (B) 1.0 (2)°, (C) -1.0 (2)° and (D) 0.2 (2)°] indicate that the acetate group in each independent molecule is coplanar with the attached quinoline ring system.

The independent molecules exist as two pseudo inversion-related pairs (A/C and B/D). In the B/D pair the centroids of the pyridine rings are separated by a distance of 3.7181 (9) Å, indicating π-π stacking interaction. Crystal packing shows each set of these molecules form sheets parallel to the ac plane. One of the sheets is shown in Fig. 2. The sheets formed by the A/C and B/D pairs are alternately stacked along the b axis. The sheets are cross-linked by C—H···O intermolecular hydrogen-bonding interactions (Fig. 3).

For related structures, see: Lynch & McClenaghan (2001); Firley et al. (2005); Yathirajan et al. (2007). For related literature, see: Padwa et al. (1999); Robert & Meunier (1998); Franck et al. (2004).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. Molecular structure of one of the independent molecules (A) in the title compound. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. A view of a sheet formed by two of the four independent molecules in the title compound, showing π-π stacking among inverted quinoline ring systems.
[Figure 3] Fig. 3. Packing diagram of the title compound, viewed down the a axis. Dashed lines indicate C—H···O hydrogen bonds.
1-(Quinolin-2-yl)ethanone top
Crystal data top
C11H9NOF(000) = 1440
Mr = 171.19Dx = 1.286 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 11806 reflections
a = 10.3292 (4) Åθ = 4.6–32.5°
b = 24.1165 (9) ŵ = 0.08 mm1
c = 15.0923 (5) ÅT = 203 K
β = 109.782 (1)°Prism, colourless
V = 3537.7 (2) Å30.49 × 0.41 × 0.19 mm
Z = 16
Data collection top
Oxford Diffraction Gemini R
diffractometer
5086 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.074
Graphite monochromatorθmax = 32.5°, θmin = 4.6°
φ and ω scansh = 1515
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2007)
k = 3336
Tmin = 0.914, Tmax = 1.000l = 2222
55457 measured reflections1 standard reflections every 50 reflections
11936 independent reflections intensity decay: none
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)] = 0.061Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.188H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0853P)2]
where P = (Fo2 + 2Fc2)/3
11936 reflections(Δ/σ)max = 0.001
473 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = 0.29 e Å3
Crystal data top
C11H9NOV = 3537.7 (2) Å3
Mr = 171.19Z = 16
Monoclinic, P21/cMo Kα radiation
a = 10.3292 (4) ŵ = 0.08 mm1
b = 24.1165 (9) ÅT = 203 K
c = 15.0923 (5) Å0.49 × 0.41 × 0.19 mm
β = 109.782 (1)°
Data collection top
Oxford Diffraction Gemini R
diffractometer
5086 reflections with I > 2σ(I)
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2007)
Rint = 0.074
Tmin = 0.914, Tmax = 1.0001 standard reflections every 50 reflections
55457 measured reflections intensity decay: none
11936 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0610 restraints
wR(F2) = 0.188H-atom parameters constrained
S = 1.01Δρmax = 0.26 e Å3
11936 reflectionsΔρmin = 0.29 e Å3
473 parameters
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
O1A0.07703 (15)1.04971 (5)0.28167 (9)0.0632 (4)
O1B0.61623 (16)0.69661 (6)0.42156 (10)0.0748 (4)
O1C0.56572 (15)0.94486 (6)0.22088 (10)0.0671 (4)
O1D0.01689 (13)0.78006 (5)0.12826 (9)0.0606 (4)
N1A0.09636 (13)0.98762 (5)0.14437 (8)0.0355 (3)
N1B0.34651 (13)0.78162 (5)0.28716 (8)0.0373 (3)
N1C0.40511 (13)1.02002 (5)0.35393 (8)0.0360 (3)
N1D0.27293 (13)0.70810 (5)0.01421 (8)0.0357 (3)
C1A0.05158 (15)1.02859 (6)0.18400 (10)0.0353 (4)
C2A0.07495 (16)1.08525 (7)0.17001 (11)0.0406 (4)
H2AA0.04081.11310.19980.049*
C3A0.14743 (16)1.09886 (7)0.11289 (11)0.0401 (4)
H3AA0.16391.13630.10280.048*
C4A0.19768 (15)1.05654 (6)0.06896 (10)0.0334 (3)
C5A0.27301 (16)1.06655 (7)0.00820 (10)0.0404 (4)
H5AA0.29231.10330.00420.048*
C6A0.31811 (18)1.02406 (7)0.03262 (11)0.0454 (4)
H6AA0.36881.03140.07260.054*
C7A0.28899 (18)0.96909 (7)0.01509 (11)0.0477 (4)
H7AA0.32010.93980.04380.057*
C8A0.21618 (17)0.95771 (7)0.04305 (11)0.0425 (4)
H8AA0.19760.92070.05420.051*
C9A0.16879 (15)1.00091 (6)0.08646 (9)0.0331 (3)
C10A0.03023 (17)1.01341 (7)0.24530 (11)0.0410 (4)
C11A0.05311 (19)0.95347 (7)0.26026 (12)0.0482 (4)
H11A0.12110.95000.29120.072*
H11B0.03270.93680.29940.072*
H11C0.08580.93460.19990.072*
C1B0.40895 (18)0.73489 (7)0.32194 (10)0.0404 (4)
C2B0.3457 (2)0.68248 (7)0.29934 (13)0.0538 (5)
H2BA0.39410.65000.32530.065*
C3B0.2143 (2)0.67967 (8)0.23973 (14)0.0576 (5)
H3BA0.17080.64500.22450.069*
C4B0.14213 (19)0.72846 (7)0.20026 (11)0.0457 (4)
C5B0.0050 (2)0.72994 (10)0.13782 (14)0.0641 (6)
H5BA0.04460.69670.12060.077*
C6B0.0568 (2)0.77907 (11)0.10202 (14)0.0671 (6)
H6BA0.14800.77930.06010.080*
C7B0.01464 (19)0.82881 (9)0.12728 (12)0.0579 (5)
H7BA0.02850.86240.10220.069*
C8B0.14661 (18)0.82904 (7)0.18805 (11)0.0467 (4)
H8BA0.19360.86290.20470.056*
C9B0.21395 (17)0.77913 (6)0.22641 (10)0.0369 (4)
C10B0.55432 (19)0.73872 (8)0.38828 (11)0.0480 (4)
C11B0.6186 (2)0.79410 (9)0.41227 (14)0.0618 (5)
H11D0.71460.78980.45080.093*
H11E0.57110.81500.44690.093*
H11F0.61230.81380.35490.093*
C1C0.44322 (15)0.97599 (6)0.31720 (10)0.0346 (3)
C2C0.41114 (17)0.92106 (7)0.33494 (11)0.0425 (4)
H2CA0.43890.89100.30590.051*
C3C0.34016 (17)0.91224 (7)0.39416 (11)0.0431 (4)
H3CA0.31870.87590.40700.052*
C4C0.29849 (15)0.95769 (7)0.43651 (10)0.0370 (4)
C5C0.22541 (17)0.95245 (8)0.49916 (11)0.0473 (4)
H5CA0.20400.91690.51580.057*
C6C0.18511 (18)0.99770 (9)0.53622 (12)0.0534 (5)
H6CA0.13520.99340.57760.064*
C7C0.21778 (19)1.05106 (9)0.51296 (13)0.0568 (5)
H7CA0.18931.08230.53880.068*
C8C0.29049 (18)1.05791 (7)0.45319 (12)0.0487 (4)
H8CA0.31271.09380.43870.058*
C9C0.33226 (15)1.01170 (7)0.41326 (10)0.0359 (4)
C10C0.52527 (17)0.98490 (7)0.25350 (11)0.0426 (4)
C11C0.55773 (19)1.04276 (7)0.23343 (12)0.0482 (4)
H11G0.61101.04210.19140.072*
H11H0.61051.06090.29190.072*
H11I0.47281.06300.20390.072*
C1D0.19891 (16)0.75186 (6)0.02455 (9)0.0345 (3)
C2D0.24719 (18)0.80692 (7)0.00719 (11)0.0426 (4)
H2DA0.19050.83680.03660.051*
C3D0.37661 (19)0.81588 (7)0.05259 (11)0.0478 (4)
H3DA0.41040.85230.06520.057*
C4D0.46046 (17)0.77089 (7)0.09584 (10)0.0395 (4)
C5D0.59782 (19)0.77644 (9)0.15884 (12)0.0535 (5)
H5DA0.63760.81180.17320.064*
C6D0.67187 (19)0.73061 (9)0.19843 (12)0.0566 (5)
H6DA0.76250.73470.24020.068*
C7D0.61497 (19)0.67772 (9)0.17777 (12)0.0551 (5)
H7DA0.66760.64660.20610.066*
C8D0.48436 (17)0.67053 (7)0.11711 (11)0.0442 (4)
H8DA0.44760.63460.10360.053*
C9D0.40373 (16)0.71704 (6)0.07426 (10)0.0365 (4)
C10D0.05534 (17)0.74153 (7)0.09018 (10)0.0403 (4)
C11D0.00576 (19)0.68309 (8)0.10771 (14)0.0571 (5)
H11J0.08880.68280.15020.086*
H11K0.01070.66590.04860.086*
H11L0.06310.66270.13570.086*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0817 (10)0.0495 (8)0.0786 (9)0.0120 (7)0.0535 (8)0.0025 (6)
O1B0.0790 (10)0.0721 (10)0.0684 (9)0.0381 (8)0.0186 (8)0.0202 (7)
O1C0.0861 (10)0.0576 (9)0.0776 (9)0.0007 (7)0.0538 (8)0.0101 (7)
O1D0.0498 (8)0.0568 (8)0.0599 (8)0.0169 (6)0.0014 (6)0.0007 (6)
N1A0.0360 (7)0.0342 (7)0.0349 (6)0.0040 (6)0.0100 (6)0.0010 (5)
N1B0.0383 (8)0.0360 (7)0.0369 (7)0.0031 (6)0.0117 (6)0.0001 (5)
N1C0.0356 (7)0.0375 (7)0.0352 (6)0.0034 (6)0.0122 (6)0.0005 (5)
N1D0.0356 (7)0.0386 (7)0.0325 (6)0.0060 (6)0.0112 (6)0.0005 (5)
C1A0.0325 (8)0.0378 (9)0.0332 (7)0.0025 (7)0.0080 (7)0.0007 (6)
C2A0.0434 (9)0.0357 (9)0.0417 (8)0.0046 (7)0.0133 (8)0.0058 (7)
C3A0.0424 (9)0.0312 (8)0.0445 (9)0.0023 (7)0.0119 (8)0.0025 (7)
C4A0.0289 (8)0.0355 (8)0.0316 (7)0.0007 (6)0.0045 (6)0.0000 (6)
C5A0.0353 (9)0.0428 (9)0.0403 (8)0.0051 (7)0.0092 (7)0.0037 (7)
C6A0.0427 (10)0.0561 (11)0.0388 (8)0.0042 (8)0.0157 (8)0.0058 (8)
C7A0.0542 (11)0.0474 (10)0.0461 (9)0.0133 (9)0.0229 (9)0.0018 (8)
C8A0.0485 (10)0.0355 (9)0.0459 (9)0.0075 (7)0.0190 (8)0.0002 (7)
C9A0.0322 (8)0.0350 (8)0.0284 (7)0.0034 (6)0.0057 (6)0.0015 (6)
C10A0.0401 (9)0.0430 (10)0.0406 (8)0.0069 (7)0.0144 (7)0.0033 (7)
C11A0.0561 (11)0.0457 (10)0.0482 (9)0.0046 (8)0.0248 (9)0.0074 (8)
C1B0.0524 (10)0.0382 (9)0.0368 (8)0.0079 (8)0.0232 (8)0.0019 (7)
C2B0.0767 (14)0.0375 (10)0.0551 (10)0.0043 (9)0.0326 (11)0.0004 (8)
C3B0.0812 (15)0.0402 (10)0.0643 (11)0.0196 (10)0.0414 (11)0.0133 (9)
C4B0.0524 (11)0.0506 (11)0.0424 (9)0.0134 (8)0.0269 (9)0.0115 (8)
C5B0.0569 (13)0.0849 (16)0.0556 (11)0.0321 (12)0.0258 (11)0.0266 (11)
C6B0.0388 (11)0.1102 (19)0.0487 (11)0.0032 (12)0.0102 (9)0.0180 (11)
C7B0.0441 (11)0.0798 (15)0.0437 (9)0.0137 (10)0.0069 (9)0.0084 (9)
C8B0.0430 (10)0.0488 (10)0.0447 (9)0.0045 (8)0.0100 (8)0.0019 (8)
C9B0.0392 (9)0.0420 (9)0.0332 (7)0.0016 (7)0.0170 (7)0.0049 (6)
C10B0.0516 (11)0.0562 (11)0.0388 (8)0.0187 (9)0.0186 (8)0.0082 (8)
C11B0.0444 (11)0.0722 (14)0.0578 (11)0.0055 (10)0.0028 (9)0.0006 (10)
C1C0.0301 (8)0.0373 (9)0.0345 (7)0.0012 (6)0.0084 (7)0.0014 (6)
C2C0.0456 (10)0.0379 (9)0.0428 (8)0.0018 (7)0.0133 (8)0.0004 (7)
C3C0.0436 (9)0.0360 (9)0.0458 (9)0.0073 (7)0.0100 (8)0.0022 (7)
C4C0.0290 (8)0.0460 (9)0.0328 (8)0.0061 (7)0.0061 (7)0.0033 (7)
C5C0.0406 (9)0.0557 (11)0.0439 (9)0.0111 (8)0.0120 (8)0.0040 (8)
C6C0.0397 (10)0.0794 (14)0.0435 (9)0.0074 (9)0.0172 (8)0.0014 (9)
C7C0.0541 (11)0.0648 (13)0.0555 (11)0.0047 (10)0.0237 (10)0.0120 (9)
C8C0.0542 (11)0.0469 (10)0.0495 (9)0.0042 (8)0.0235 (9)0.0036 (8)
C9C0.0284 (8)0.0426 (9)0.0322 (7)0.0030 (7)0.0043 (7)0.0003 (6)
C10C0.0420 (9)0.0483 (10)0.0385 (8)0.0011 (8)0.0149 (8)0.0025 (7)
C11C0.0487 (10)0.0552 (11)0.0438 (9)0.0046 (9)0.0196 (8)0.0072 (8)
C1D0.0370 (8)0.0398 (9)0.0282 (7)0.0071 (7)0.0129 (7)0.0014 (6)
C2D0.0503 (10)0.0360 (9)0.0406 (8)0.0086 (8)0.0142 (8)0.0001 (7)
C3D0.0532 (11)0.0402 (9)0.0477 (9)0.0040 (8)0.0138 (9)0.0057 (7)
C4D0.0378 (9)0.0488 (10)0.0338 (8)0.0004 (7)0.0144 (7)0.0032 (7)
C5D0.0424 (10)0.0699 (13)0.0458 (10)0.0072 (9)0.0116 (9)0.0077 (9)
C6D0.0329 (9)0.0939 (16)0.0384 (9)0.0066 (10)0.0062 (8)0.0008 (10)
C7D0.0491 (11)0.0734 (14)0.0414 (9)0.0198 (10)0.0133 (9)0.0068 (9)
C8D0.0428 (10)0.0514 (10)0.0382 (8)0.0123 (8)0.0135 (8)0.0036 (7)
C9D0.0345 (8)0.0452 (9)0.0318 (7)0.0062 (7)0.0140 (7)0.0011 (6)
C10D0.0385 (9)0.0466 (10)0.0351 (8)0.0067 (8)0.0116 (7)0.0041 (7)
C11D0.0453 (11)0.0532 (11)0.0646 (11)0.0002 (9)0.0077 (9)0.0086 (9)
Geometric parameters (Å, º) top
O1A—C10A1.2170 (19)C8B—C9B1.412 (2)
O1B—C10B1.214 (2)C8B—H8BA0.94
O1C—C10C1.220 (2)C10B—C11B1.481 (3)
O1D—C10D1.2084 (18)C11B—H11D0.97
N1A—C1A1.3173 (19)C11B—H11E0.97
N1A—C9A1.3671 (19)C11B—H11F0.97
N1B—C1B1.3162 (19)C1C—C2C1.413 (2)
N1B—C9B1.367 (2)C1C—C10C1.497 (2)
N1C—C1C1.318 (2)C2C—C3C1.351 (2)
N1C—C9C1.3653 (19)C2C—H2CA0.94
N1D—C1D1.3183 (19)C3C—C4C1.408 (2)
N1D—C9D1.3654 (19)C3C—H3CA0.94
C1A—C2A1.416 (2)C4C—C5C1.401 (2)
C1A—C10A1.494 (2)C4C—C9C1.423 (2)
C2A—C3A1.360 (2)C5C—C6C1.354 (3)
C2A—H2AA0.94C5C—H5CA0.94
C3A—C4A1.408 (2)C6C—C7C1.405 (3)
C3A—H3AA0.94C6C—H6CA0.94
C4A—C5A1.410 (2)C7C—C8C1.365 (2)
C4A—C9A1.419 (2)C7C—H7CA0.94
C5A—C6A1.357 (2)C8C—C9C1.403 (2)
C5A—H5AA0.94C8C—H8CA0.94
C6A—C7A1.404 (2)C10C—C11C1.490 (2)
C6A—H6AA0.94C11C—H11G0.97
C7A—C8A1.363 (2)C11C—H11H0.97
C7A—H7AA0.94C11C—H11I0.97
C8A—C9A1.404 (2)C1D—C2D1.411 (2)
C8A—H8AA0.94C1D—C10D1.499 (2)
C10A—C11A1.494 (2)C2D—C3D1.353 (2)
C11A—H11A0.97C2D—H2DA0.94
C11A—H11B0.97C3D—C4D1.404 (2)
C11A—H11C0.97C3D—H3DA0.94
C1B—C2B1.411 (2)C4D—C9D1.417 (2)
C1B—C10B1.499 (2)C4D—C5D1.422 (2)
C2B—C3B1.352 (3)C5D—C6D1.362 (3)
C2B—H2BA0.94C5D—H5DA0.94
C3B—C4B1.413 (3)C6D—C7D1.395 (3)
C3B—H3BA0.94C6D—H6DA0.94
C4B—C5B1.411 (3)C7D—C8D1.361 (2)
C4B—C9B1.415 (2)C7D—H7DA0.94
C5B—C6B1.367 (3)C8D—C9D1.416 (2)
C5B—H5BA0.94C8D—H8DA0.94
C6B—C7B1.392 (3)C10D—C11D1.492 (2)
C6B—H6BA0.94C11D—H11J0.97
C7B—C8B1.361 (2)C11D—H11K0.97
C7B—H7BA0.94C11D—H11L0.97
C1A—N1A—C9A117.82 (13)H11D—C11B—H11F109.5
C1B—N1B—C9B118.31 (14)H11E—C11B—H11F109.5
C1C—N1C—C9C117.83 (13)N1C—C1C—C2C123.57 (15)
C1D—N1D—C9D117.59 (14)N1C—C1C—C10C117.99 (14)
N1A—C1A—C2A123.53 (15)C2C—C1C—C10C118.44 (15)
N1A—C1A—C10A117.15 (14)C3C—C2C—C1C119.18 (16)
C2A—C1A—C10A119.31 (14)C3C—C2C—H2CA120.4
C3A—C2A—C1A119.06 (15)C1C—C2C—H2CA120.4
C3A—C2A—H2AA120.5C2C—C3C—C4C119.70 (15)
C1A—C2A—H2AA120.5C2C—C3C—H3CA120.1
C2A—C3A—C4A119.57 (15)C4C—C3C—H3CA120.1
C2A—C3A—H3AA120.2C5C—C4C—C3C123.61 (15)
C4A—C3A—H3AA120.2C5C—C4C—C9C118.82 (15)
C3A—C4A—C5A123.68 (14)C3C—C4C—C9C117.57 (14)
C3A—C4A—C9A117.61 (14)C6C—C5C—C4C121.14 (17)
C5A—C4A—C9A118.70 (14)C6C—C5C—H5CA119.4
C6A—C5A—C4A121.06 (15)C4C—C5C—H5CA119.4
C6A—C5A—H5AA119.5C5C—C6C—C7C120.09 (18)
C4A—C5A—H5AA119.5C5C—C6C—H6CA120.0
C5A—C6A—C7A119.94 (16)C7C—C6C—H6CA120.0
C5A—C6A—H6AA120.0C8C—C7C—C6C120.56 (18)
C7A—C6A—H6AA120.0C8C—C7C—H7CA119.7
C8A—C7A—C6A120.76 (16)C6C—C7C—H7CA119.7
C8A—C7A—H7AA119.6C7C—C8C—C9C120.39 (17)
C6A—C7A—H7AA119.6C7C—C8C—H8CA119.8
C7A—C8A—C9A120.43 (16)C9C—C8C—H8CA119.8
C7A—C8A—H8AA119.8N1C—C9C—C8C118.89 (15)
C9A—C8A—H8AA119.8N1C—C9C—C4C122.12 (14)
N1A—C9A—C8A118.49 (14)C8C—C9C—C4C118.99 (15)
N1A—C9A—C4A122.41 (13)O1C—C10C—C11C121.86 (16)
C8A—C9A—C4A119.10 (14)O1C—C10C—C1C119.43 (16)
O1A—C10A—C11A121.36 (16)C11C—C10C—C1C118.70 (15)
O1A—C10A—C1A119.82 (15)C10C—C11C—H11G109.5
C11A—C10A—C1A118.83 (14)C10C—C11C—H11H109.5
C10A—C11A—H11A109.5H11G—C11C—H11H109.5
C10A—C11A—H11B109.5C10C—C11C—H11I109.5
H11A—C11A—H11B109.5H11G—C11C—H11I109.5
C10A—C11A—H11C109.5H11H—C11C—H11I109.5
H11A—C11A—H11C109.5N1D—C1D—C2D123.74 (14)
H11B—C11A—H11C109.5N1D—C1D—C10D117.10 (14)
N1B—C1B—C2B123.13 (17)C2D—C1D—C10D119.16 (14)
N1B—C1B—C10B117.29 (15)C3D—C2D—C1D118.76 (15)
C2B—C1B—C10B119.58 (16)C3D—C2D—H2DA120.6
C3B—C2B—C1B118.95 (17)C1D—C2D—H2DA120.6
C3B—C2B—H2BA120.5C2D—C3D—C4D120.10 (16)
C1B—C2B—H2BA120.5C2D—C3D—H3DA120.0
C2B—C3B—C4B120.43 (17)C4D—C3D—H3DA120.0
C2B—C3B—H3BA119.8C3D—C4D—C9D117.36 (15)
C4B—C3B—H3BA119.8C3D—C4D—C5D123.86 (16)
C5B—C4B—C3B124.74 (18)C9D—C4D—C5D118.78 (16)
C5B—C4B—C9B118.52 (18)C6D—C5D—C4D120.14 (18)
C3B—C4B—C9B116.73 (17)C6D—C5D—H5DA119.9
C6B—C5B—C4B120.96 (19)C4D—C5D—H5DA119.9
C6B—C5B—H5BA119.5C5D—C6D—C7D120.83 (17)
C4B—C5B—H5BA119.5C5D—C6D—H6DA119.6
C5B—C6B—C7B120.34 (19)C7D—C6D—H6DA119.6
C5B—C6B—H6BA119.8C8D—C7D—C6D120.91 (17)
C7B—C6B—H6BA119.8C8D—C7D—H7DA119.5
C8B—C7B—C6B120.33 (19)C6D—C7D—H7DA119.5
C8B—C7B—H7BA119.8C7D—C8D—C9D120.14 (17)
C6B—C7B—H7BA119.8C7D—C8D—H8DA119.9
C7B—C8B—C9B120.97 (17)C9D—C8D—H8DA119.9
C7B—C8B—H8BA119.5N1D—C9D—C8D118.36 (15)
C9B—C8B—H8BA119.5N1D—C9D—C4D122.46 (14)
N1B—C9B—C8B118.68 (14)C8D—C9D—C4D119.18 (15)
N1B—C9B—C4B122.45 (15)O1D—C10D—C11D121.49 (15)
C8B—C9B—C4B118.86 (16)O1D—C10D—C1D119.99 (15)
O1B—C10B—C11B121.54 (18)C11D—C10D—C1D118.52 (14)
O1B—C10B—C1B119.53 (18)C10D—C11D—H11J109.5
C11B—C10B—C1B118.93 (15)C10D—C11D—H11K109.5
C10B—C11B—H11D109.5H11J—C11D—H11K109.5
C10B—C11B—H11E109.5C10D—C11D—H11L109.5
H11D—C11B—H11E109.5H11J—C11D—H11L109.5
C10B—C11B—H11F109.5H11K—C11D—H11L109.5
C9A—N1A—C1A—C2A0.2 (2)C9C—N1C—C1C—C2C0.9 (2)
C9A—N1A—C1A—C10A178.60 (12)C9C—N1C—C1C—C10C178.92 (13)
N1A—C1A—C2A—C3A0.1 (2)N1C—C1C—C2C—C3C1.5 (2)
C10A—C1A—C2A—C3A178.89 (14)C10C—C1C—C2C—C3C178.34 (14)
C1A—C2A—C3A—C4A0.0 (2)C1C—C2C—C3C—C4C0.5 (2)
C2A—C3A—C4A—C5A179.59 (14)C2C—C3C—C4C—C5C179.58 (15)
C2A—C3A—C4A—C9A0.4 (2)C2C—C3C—C4C—C9C0.9 (2)
C3A—C4A—C5A—C6A179.58 (15)C3C—C4C—C5C—C6C178.47 (15)
C9A—C4A—C5A—C6A0.4 (2)C9C—C4C—C5C—C6C1.1 (2)
C4A—C5A—C6A—C7A0.5 (2)C4C—C5C—C6C—C7C0.8 (3)
C5A—C6A—C7A—C8A0.3 (3)C5C—C6C—C7C—C8C0.2 (3)
C6A—C7A—C8A—C9A0.1 (2)C6C—C7C—C8C—C9C0.8 (3)
C1A—N1A—C9A—C8A179.46 (13)C1C—N1C—C9C—C8C179.97 (14)
C1A—N1A—C9A—C4A0.6 (2)C1C—N1C—C9C—C4C0.6 (2)
C7A—C8A—C9A—N1A179.89 (14)C7C—C8C—C9C—N1C179.86 (15)
C7A—C8A—C9A—C4A0.0 (2)C7C—C8C—C9C—C4C0.4 (2)
C3A—C4A—C9A—N1A0.7 (2)C5C—C4C—C9C—N1C178.95 (13)
C5A—C4A—C9A—N1A179.96 (13)C3C—C4C—C9C—N1C1.5 (2)
C3A—C4A—C9A—C8A179.38 (13)C5C—C4C—C9C—C8C0.5 (2)
C5A—C4A—C9A—C8A0.1 (2)C3C—C4C—C9C—C8C179.09 (14)
N1A—C1A—C10A—O1A178.13 (15)N1C—C1C—C10C—O1C177.67 (15)
C2A—C1A—C10A—O1A0.8 (2)C2C—C1C—C10C—O1C2.2 (2)
N1A—C1A—C10A—C11A1.7 (2)N1C—C1C—C10C—C11C1.0 (2)
C2A—C1A—C10A—C11A179.44 (14)C2C—C1C—C10C—C11C179.15 (14)
C9B—N1B—C1B—C2B0.2 (2)C9D—N1D—C1D—C2D0.2 (2)
C9B—N1B—C1B—C10B179.92 (13)C9D—N1D—C1D—C10D179.85 (12)
N1B—C1B—C2B—C3B0.5 (3)N1D—C1D—C2D—C3D0.1 (2)
C10B—C1B—C2B—C3B179.72 (15)C10D—C1D—C2D—C3D179.60 (14)
C1B—C2B—C3B—C4B0.5 (3)C1D—C2D—C3D—C4D0.2 (2)
C2B—C3B—C4B—C5B179.74 (17)C2D—C3D—C4D—C9D0.1 (2)
C2B—C3B—C4B—C9B0.1 (3)C2D—C3D—C4D—C5D179.46 (16)
C3B—C4B—C5B—C6B179.29 (18)C3D—C4D—C5D—C6D179.45 (16)
C9B—C4B—C5B—C6B1.0 (3)C9D—C4D—C5D—C6D1.0 (2)
C4B—C5B—C6B—C7B0.5 (3)C4D—C5D—C6D—C7D0.3 (3)
C5B—C6B—C7B—C8B0.2 (3)C5D—C6D—C7D—C8D0.4 (3)
C6B—C7B—C8B—C9B0.2 (3)C6D—C7D—C8D—C9D0.3 (3)
C1B—N1B—C9B—C8B179.41 (14)C1D—N1D—C9D—C8D179.52 (13)
C1B—N1B—C9B—C4B0.3 (2)C1D—N1D—C9D—C4D0.3 (2)
C7B—C8B—C9B—N1B179.98 (15)C7D—C8D—C9D—N1D179.66 (14)
C7B—C8B—C9B—C4B0.3 (2)C7D—C8D—C9D—C4D0.4 (2)
C5B—C4B—C9B—N1B179.38 (14)C3D—C4D—C9D—N1D0.1 (2)
C3B—C4B—C9B—N1B0.3 (2)C5D—C4D—C9D—N1D179.74 (14)
C5B—C4B—C9B—C8B0.9 (2)C3D—C4D—C9D—C8D179.36 (14)
C3B—C4B—C9B—C8B179.36 (15)C5D—C4D—C9D—C8D1.0 (2)
N1B—C1B—C10B—O1B179.49 (15)N1D—C1D—C10D—O1D179.47 (14)
C2B—C1B—C10B—O1B0.3 (2)C2D—C1D—C10D—O1D0.8 (2)
N1B—C1B—C10B—C11B1.0 (2)N1D—C1D—C10D—C11D0.2 (2)
C2B—C1B—C10B—C11B179.21 (16)C2D—C1D—C10D—C11D179.92 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3B—H3BA···O1Ai0.942.483.410 (2)169
C6D—H6DA···O1Dii0.942.493.399 (2)163
Symmetry codes: (i) x, y1/2, z+1/2; (ii) x+1, y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC11H9NO
Mr171.19
Crystal system, space groupMonoclinic, P21/c
Temperature (K)203
a, b, c (Å)10.3292 (4), 24.1165 (9), 15.0923 (5)
β (°) 109.782 (1)
V3)3537.7 (2)
Z16
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.49 × 0.41 × 0.19
Data collection
DiffractometerOxford Diffraction Gemini R
Absorption correctionMulti-scan
(CrysAlis PRO; Oxford Diffraction, 2007)
Tmin, Tmax0.914, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
55457, 11936, 5086
Rint0.074
(sin θ/λ)max1)0.757
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.061, 0.188, 1.01
No. of reflections11936
No. of parameters473
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.26, 0.29

Computer programs: CrysAlis PRO (Oxford Diffraction, 2007), CrysAlis PRO, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3B—H3BA···O1Ai0.942.483.410 (2)169
C6D—H6DA···O1Dii0.942.493.399 (2)163
Symmetry codes: (i) x, y1/2, z+1/2; (ii) x+1, y+3/2, z+1/2.
 

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