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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 12| December 2010| Page o3146
https://doi.org/10.1107/S1600536810045769

1-(1-Hy­dr­oxy-8-methyl-9H-carbazol-2-yl)ethanone

R. Archana,a K. Prabakaran,b K. J. Rajendra Prasad,b A. Thiruvalluvara* and R. J. Butcherc

aPG Research Department of Physics, Rajah Serfoji Government College (Autonomous), Thanjavur 613 005, Tamilnadu, India, bDepartment of Chemistry, Bharathiar University, Coimbatore 641 046, Tamilnadu, India, and cDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA
*Correspondence e-mail: thiruvalluvar.a@gmail.com

(Received 23 October 2010; accepted 7 November 2010; online 13 November 2010)

The title compound, C15H13NO2, crystallizes with four independent mol­ecules (A, B, C and D) in the asymmetric unit. The carbazole units are almost planar [maximum deviations = 0.015 (3) for A, 0.024 (3) for B, 0.026 (3) for C and 0.046 (3) Å for D]. In all four mol­ecules, there is an O—H⋯O hydrogen bond involving the hy­droxy substituent and the carbonyl O atom of the adjacent acetyl group, which forms a six-membered ring. In the crystal, the four independent mol­ecules are linked via N—H⋯O and C—H⋯O inter­actions.

Related literature

For the biological and pharmacological activity of carbazole alkaloids, see: Hagiwara et al. (2000[Hagiwara, H., Choshi, T., Fujimoto, H., Sugino, E. & Hibino, S. (2000). Tetrahedron, 56, 5807-5811.]); Randelia & Patel (1982[Randelia, B. E. & Patel, B. P. J. (1982). Cell. Mol. Life Sci. 38, 529-531.]); Tovey et al. (1998[Tovey, S. C., Longland, C. L., Mezna, M. & Michelangeli, F. (1998). Eur. J. Pharm. 354, 245-251.]). For the synthesis of various hetero-annulated carbazole derivatives, see: Vandana & Prasad (2004[Vandana, T. & Prasad, K. J. R. (2004). J. Chem. Res. pp. 717-721.]); Vandana et al. (2004[Vandana, T., Prasad, K. J. R. & Sowmithran, D. (2004). Indian J. Chem. Sect. B, 43, 2405-2409.]).

[Scheme 1]

Experimental

Crystal data

  • C15H13NO2

  • Mr = 239.26

  • Monoclinic, P 21

  • a = 7.4602 (2) Å

  • b = 12.7353 (3) Å

  • c = 24.9325 (5) Å

  • β = 92.319 (2)°

  • V = 2366.84 (10) Å3

  • Z = 8

  • Cu Kα radiation

  • μ = 0.72 mm−1

  • T = 295 K

  • 0.47 × 0.31 × 0.11 mm
Data collection

  • Oxford Diffraction Xcalibur Ruby Gemini diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]) Tmin = 0.746, Tmax = 1.000

  • 4770 measured reflections

  • 4770 independent reflections

  • 4075 reflections with I > 2σ(I)
Refinement

  • R[F2 > 2σ(F2)] = 0.042

  • wR(F2) = 0.122

  • S = 1.05

  • 4770 reflections

  • 685 parameters

  • 5 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.16 e Å−3

  • Δρmin = −0.18 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1A—H1A⋯O14A 0.85 (4) 1.80 (4) 2.563 (3) 147 (5)
O1B—H1B⋯O14B 0.83 (4) 1.85 (4) 2.574 (4) 145 (5)
O1C—H1C⋯O14C 0.84 (3) 1.79 (3) 2.575 (4) 156 (5)
O1D—H1D⋯O14D 0.85 (4) 1.87 (4) 2.573 (4) 139 (5)
N12A—H12A⋯O14Bi 0.79 (5) 2.27 (5) 3.052 (4) 172 (5)
N12B—H12B⋯O14Ai 0.93 (5) 2.33 (5) 3.176 (4) 153 (5)
N12C—H12C⋯O14Dii 0.88 (4) 2.28 (4) 3.133 (4) 163 (3)
N12D—H12D⋯O14Cii 0.86 (4) 2.26 (4) 3.105 (4) 168 (3)
C15A—H15A⋯O1Biii 0.96 2.47 3.422 (5) 173
C15B—H15D⋯O1Aiii 0.96 2.60 3.433 (5) 145
C15C—H15I⋯O1Div 0.96 2.53 3.445 (5) 160
C15D—H15J⋯O1Civ 0.96 2.44 3.388 (5) 170
Symmetry codes: (i) [-x+1, y-{\script{1\over 2}}, -z]; (ii) [-x+1, y+{\script{1\over 2}}, -z+1]; (iii) [-x+1, y+{\script{1\over 2}}, -z]; (iv) [-x+1, y-{\script{1\over 2}}, -z+1].

Data collection: CrysAlis PRO (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810045769/hg2736sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810045769/hg2736Isup2.hkl

checkCIF report


Comment top

The isolation of carbazole alkaloids became an active area of study since these compounds possess high levels of biological and pharmacological activity (Hagiwara et al., (2000); Randelia & Patel (1982); Tovey et al., (1998)). 2-acetyl-9H-carbazol-1-ol is a versatile intermediate to synthesis various hetero-annulated carbazole derivatives (Vandana & Prasad (2004); Vandana et al., (2004)). The preparation of 2-acetyl-9H-carbazol-1-ol from 1-hydroxycarbazole with acetic acid and ZnCl2/POCl3 was tedious process and poor yield (22%). But in the case of 2,3,4,9-tetrahydrocarbazol-1-one with ethyl acetate in the presence of NaH/KH furnished moderate yield (38%).

The title compound, C15H13NO2, crystallizes in the monoclinic space group P21, with four independent molecules (A,B,C and D) in the asymmetric unit. The carbazole units are almost planar. In all the four molecules, there is an O—H···O hydrogen bond involving the hydroxy substituent and the carbonyl O atom of the adjacent acetyl group, forming six-membered rings. In the crystal structure, molecules A,B,C and D are linked via N—H···O and C—H···O interactions (Table 1 & Fig. 3).

Related literature top

For the biological and pharmacological activity of carbazole alkaloids, see: Hagiwara et al. (2000); Randelia & Patel (1982); Tovey et al. (1998). For the synthesis of various hetero-annulated carbazole derivatives, see: Vandana & Prasad (2004); Vandana et al. (2004).

Experimental top

To the suspension of 60% sodium hydride (2.4 g, 0.06 mol) in benzene (20 ml) 8-methyl-2,3,4,9-tetrahydrocarbazol-1-one (1.6 g, 0.008 mol) was added. It was heated on a water bath for 5 min. Then small amount of potassium hydride was added carefully (caution: Dry potassium hydride is highly pyrophoric since it may contain potassium metal). It was allowed to reflux. To this mixture, ethyl acetate was added drop by drop. After the addition was completed it was allowed to reflux for 2 h. The solution was cooled, neutralized with glacial acetic acid, poured into ice water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and the solvent was removed to get a crude mass. It was purified by column chromatography over silica gel using petroleum ether as eluant (yield: 0.726 g, 38%). It was crystallized from ethanol.

Refinement top

Owing to the absence of any anamalous scatterers in the molecule, the Friedel pairs were merged. The absolute structure in the present model have been chosen arbitrarily. H12A, H12B, H12C & H12D attached to the corresponding N atoms were located in a difference Fourier map and refined freely. H1A, H1B, H1C & H1D attached to the corresponding O atoms were located in a difference Fourier map and refined with O—H DFIX (0.84 (2) Å) restraints. The remaining H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.93 and 0.96 Å for Csp2 and methyl H atoms, respectively. Uiso(H) = xUeq(C), where x = 1.5 for methyl H atoms and 1.2 for other C-bound H atoms.

Structure description top

The isolation of carbazole alkaloids became an active area of study since these compounds possess high levels of biological and pharmacological activity (Hagiwara et al., (2000); Randelia & Patel (1982); Tovey et al., (1998)). 2-acetyl-9H-carbazol-1-ol is a versatile intermediate to synthesis various hetero-annulated carbazole derivatives (Vandana & Prasad (2004); Vandana et al., (2004)). The preparation of 2-acetyl-9H-carbazol-1-ol from 1-hydroxycarbazole with acetic acid and ZnCl2/POCl3 was tedious process and poor yield (22%). But in the case of 2,3,4,9-tetrahydrocarbazol-1-one with ethyl acetate in the presence of NaH/KH furnished moderate yield (38%).

The title compound, C15H13NO2, crystallizes in the monoclinic space group P21, with four independent molecules (A,B,C and D) in the asymmetric unit. The carbazole units are almost planar. In all the four molecules, there is an O—H···O hydrogen bond involving the hydroxy substituent and the carbonyl O atom of the adjacent acetyl group, forming six-membered rings. In the crystal structure, molecules A,B,C and D are linked via N—H···O and C—H···O interactions (Table 1 & Fig. 3).

For the biological and pharmacological activity of carbazole alkaloids, see: Hagiwara et al. (2000); Randelia & Patel (1982); Tovey et al. (1998). For the synthesis of various hetero-annulated carbazole derivatives, see: Vandana & Prasad (2004); Vandana et al. (2004).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. A view of the molecular structure of the two independent molecules (A and B), showing the atom-numbering scheme and displacement ellipsoids drawn at the 30% probability level. H atoms are shown as small spheres of arbitrary radius and the intramolecular O—H···O hydrogen bonds as dashed lines.
[Figure 2] Fig. 2. A view of the molecular structure of the two independent molecules (C and D), showing the atom-numbering scheme and displacement ellipsoids drawn at the 30% probability level. H atoms are shown as small spheres of arbitrary radius and the intramolecular O—H···O hydrogen bonds as dashed lines.
[Figure 3] Fig. 3. The molecular packing of the title compound, viewed down the a axis. Dashed lines indicate hydrogen bonds. H atoms not involved in hydrogen bonding have been omitted.
1-(1-Hydroxy-8-methyl-9H-carbazol-2-yl)ethanone top
Crystal data top
C15H13NO2F(000) = 1008
Mr = 239.26Dx = 1.343 Mg m−3
Monoclinic, P21Melting point: 485 K
Hall symbol: P 2ybCu Kα radiation, λ = 1.54184 Å
a = 7.4602 (2) ÅCell parameters from 4181 reflections
b = 12.7353 (3) Åθ = 5.0–72.6°
c = 24.9325 (5) ŵ = 0.72 mm−1
β = 92.319 (2)°T = 295 K
V = 2366.84 (10) Å3Plate, pale yellow-orange
Z = 80.47 × 0.31 × 0.11 mm
Data collection top
Oxford Diffraction Xcalibur Ruby Gemini
diffractometer		4770 independent reflections
Radiation source: Enhance (Cu) X-ray Source4075 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.000
Detector resolution: 10.5081 pixels mm-1θmax = 72.8°, θmin = 5.0°
ω scansh = −8→8
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2010)		k = 0→15
Tmin = 0.746, Tmax = 1.000l = 0→30
4770 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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.075P)2]
where P = (Fo2 + 2Fc2)/3
4770 reflections(Δ/σ)max = 0.001
685 parametersΔρmax = 0.16 e Å−3
5 restraintsΔρmin = −0.18 e Å−3
Crystal data top
C15H13NO2V = 2366.84 (10) Å3
Mr = 239.26Z = 8
Monoclinic, P21Cu Kα radiation
a = 7.4602 (2) ŵ = 0.72 mm−1
b = 12.7353 (3) ÅT = 295 K
c = 24.9325 (5) Å0.47 × 0.31 × 0.11 mm
β = 92.319 (2)°
Data collection top
Oxford Diffraction Xcalibur Ruby Gemini
diffractometer		4770 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2010)		4075 reflections with I > 2σ(I)
Tmin = 0.746, Tmax = 1.000Rint = 0.000
4770 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0425 restraints
wR(F2) = 0.122H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.16 e Å−3
4770 reflectionsΔρmin = −0.18 e Å−3
685 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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 > 2σ(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
O1A0.1525 (4)1.05674 (18)−0.05071 (10)0.0640 (8)
O14A0.1171 (4)1.25605 (19)−0.06053 (11)0.0675 (9)
N12A0.2811 (4)0.8882 (2)0.01958 (12)0.0533 (8)
C1A0.2302 (4)1.0783 (3)−0.00238 (13)0.0508 (9)
C2A0.2542 (4)1.1806 (3)0.01736 (13)0.0525 (9)
C3A0.3381 (5)1.1961 (3)0.06884 (14)0.0590 (10)
C4A0.3951 (5)1.1146 (3)0.10034 (14)0.0581 (11)
C5A0.3719 (4)1.0114 (3)0.08106 (13)0.0511 (9)
C6A0.4120 (4)0.9095 (3)0.10274 (14)0.0523 (9)
C7A0.4916 (5)0.8752 (3)0.15137 (15)0.0618 (11)
C8A0.5134 (5)0.7691 (3)0.15940 (16)0.0698 (12)
C9A0.4583 (5)0.6973 (3)0.12009 (16)0.0665 (11)
C10A0.3757 (4)0.7269 (3)0.07168 (15)0.0560 (10)
C11A0.3545 (4)0.8356 (3)0.06368 (14)0.0522 (9)
C13A0.2899 (4)0.9948 (2)0.03020 (13)0.0489 (9)
C14A0.1936 (5)1.2698 (3)−0.01600 (15)0.0578 (10)
C15A0.2219 (6)1.3809 (3)0.00336 (18)0.0706 (15)
C16A0.3108 (6)0.6483 (3)0.03121 (18)0.0725 (15)
O1B0.9083 (4)1.0667 (2)0.08942 (10)0.0659 (8)
O14B0.8515 (4)1.2652 (2)0.07931 (11)0.0722 (9)
N12B0.9425 (4)0.8947 (2)0.16560 (13)0.0597 (9)
C1B0.8865 (4)1.0842 (2)0.14183 (13)0.0501 (9)
C2B0.8459 (4)1.1829 (2)0.16315 (13)0.0507 (9)
C3B0.8269 (4)1.1929 (3)0.21987 (14)0.0590 (10)
C4B0.8462 (5)1.1094 (3)0.25346 (15)0.0611 (11)
C5B0.8831 (4)1.0106 (3)0.23219 (13)0.0544 (10)
C6B0.9096 (4)0.9088 (3)0.25566 (14)0.0593 (11)
C7B0.9062 (5)0.8711 (3)0.30863 (16)0.0723 (12)
C8B0.9356 (6)0.7660 (4)0.31717 (19)0.0838 (17)
C9B0.9663 (6)0.6985 (3)0.2750 (2)0.0818 (14)
C10B0.9708 (5)0.7320 (3)0.22232 (18)0.0702 (13)
C11B0.9446 (5)0.8405 (3)0.21344 (16)0.0597 (11)
C13B0.9033 (4)0.9982 (2)0.17697 (13)0.0515 (9)
C14B0.8236 (4)1.2732 (3)0.12768 (15)0.0587 (11)
C15B0.7684 (7)1.3769 (3)0.14954 (18)0.0799 (15)
C16B0.9942 (7)0.6594 (4)0.1777 (2)0.0906 (17)
O1C0.6222 (4)0.12255 (19)0.39711 (11)0.0732 (9)
O14C0.6010 (4)−0.0771 (2)0.41193 (11)0.0732 (9)
N12C0.5247 (4)0.2935 (2)0.32494 (12)0.0565 (9)
C1C0.5248 (4)0.1036 (3)0.35163 (13)0.0536 (10)
C2C0.4680 (4)0.0027 (3)0.33534 (13)0.0529 (9)
C3C0.3690 (4)−0.0085 (3)0.28552 (14)0.0561 (10)
C4C0.3249 (4)0.0744 (3)0.25361 (14)0.0563 (10)
C5C0.3806 (4)0.1755 (3)0.26976 (12)0.0506 (9)
C6C0.3622 (4)0.2777 (3)0.24613 (13)0.0525 (9)
C7C0.2774 (5)0.3146 (3)0.19935 (14)0.0613 (11)
C8C0.2835 (5)0.4202 (3)0.18826 (15)0.0677 (11)
C9C0.3741 (5)0.4886 (3)0.22329 (15)0.0678 (11)
C10C0.4615 (5)0.4565 (3)0.26995 (14)0.0596 (11)
C11C0.4534 (4)0.3482 (3)0.28116 (13)0.0528 (9)
C13C0.4791 (4)0.1886 (3)0.31835 (13)0.0511 (9)
C14C0.5118 (5)−0.0873 (3)0.36943 (14)0.0593 (11)
C15C0.4478 (7)−0.1955 (3)0.3533 (2)0.0813 (15)
C16C0.5571 (7)0.5312 (3)0.30756 (18)0.0819 (16)
O1D0.3083 (4)0.13066 (19)0.56704 (10)0.0687 (9)
O14D0.3287 (4)−0.0698 (2)0.57844 (11)0.0747 (9)
N12D0.2317 (4)0.2998 (2)0.49087 (11)0.0527 (8)
C1D0.2471 (4)0.1091 (3)0.51683 (13)0.0516 (9)
C2D0.2215 (4)0.0063 (3)0.49717 (13)0.0522 (10)
C3D0.1537 (5)−0.0082 (3)0.44362 (14)0.0590 (11)
C4D0.1133 (5)0.0739 (3)0.41025 (13)0.0602 (11)
C5D0.1438 (4)0.1768 (3)0.42924 (12)0.0512 (9)
C6D0.1252 (4)0.2783 (3)0.40517 (13)0.0545 (10)
C7D0.0669 (5)0.3119 (3)0.35375 (14)0.0666 (11)
C8D0.0673 (6)0.4169 (3)0.34277 (16)0.0739 (14)
C9D0.1248 (6)0.4891 (3)0.38213 (16)0.0680 (11)
C10D0.1850 (5)0.4605 (3)0.43328 (15)0.0579 (11)
C11D0.1813 (4)0.3520 (3)0.44388 (13)0.0519 (10)
C13D0.2106 (4)0.1931 (2)0.48165 (13)0.0494 (9)
C14D0.2714 (5)−0.0830 (3)0.53138 (15)0.0566 (10)
C15D0.2613 (6)−0.1924 (3)0.51031 (17)0.0701 (11)
C16D0.2479 (6)0.5384 (3)0.47376 (17)0.0713 (15)
H1A0.126 (8)1.115 (3)−0.066 (2)0.1089*
H3A0.354691.264300.081450.0706*
H4A0.448561.126860.134110.0696*
H7A0.528920.923110.177690.0740*
H8A0.565700.744930.191570.0837*
H9A0.477740.626260.126590.0797*
H12A0.237 (7)0.860 (4)−0.0058 (19)0.085 (15)*
H15A0.176401.42889−0.023570.1059*
H15B0.347731.393220.010100.1059*
H15C0.159551.391230.035880.1059*
H16A0.343900.579100.043220.1089*
H16B0.364040.66235−0.002460.1089*
H16C0.182610.652820.026770.1089*
H1B0.908 (9)1.124 (3)0.074 (2)0.1359*
H3B0.800591.258330.234070.0708*
H4B0.835001.117890.290220.0733*
H7B0.884640.916110.337030.0863*
H8B0.934760.739530.351930.1006*
H9B0.984760.627650.282430.0978*
H12B0.955 (7)0.870 (4)0.131 (2)0.091 (15)*
H15D0.734281.422970.120420.1200*
H15E0.866941.407090.170140.1200*
H15F0.668511.367220.172120.1200*
H16D1.032310.592240.191430.1359*
H16E1.083240.686600.154640.1359*
H16F0.882400.651630.157600.1359*
H1C0.617 (9)0.063 (2)0.411 (2)0.1225*
H3C0.33337−0.075370.274510.0673*
H4C0.258900.064600.221560.0675*
H7C0.217270.268620.175870.0734*
H8C0.226640.446030.157110.0810*
H9C0.375590.559630.214690.0811*
H12C0.580 (5)0.320 (3)0.3536 (15)0.051 (9)*
H15G0.49524−0.213800.319300.1219*
H15H0.31910−0.196160.350330.1219*
H15I0.48832−0.245450.379950.1219*
H16G0.490780.538430.339540.1225*
H16H0.567130.598390.290530.1225*
H16I0.674800.504560.316730.1225*
H1D0.345 (7)0.076 (3)0.584 (2)0.1067*
H3D0.13630−0.076240.430860.0708*
H4D0.066500.062290.375620.0723*
H7D0.028790.263660.327720.0799*
H8D0.029010.440590.308930.0886*
H9D0.122590.560070.373430.0816*
H12D0.273 (5)0.326 (3)0.5207 (17)0.065 (11)*
H15J0.30862−0.239990.537160.1051*
H15K0.33029−0.197610.478750.1051*
H15L0.13852−0.209940.501460.1051*
H16J0.256390.606130.457160.1067*
H16K0.363760.517960.488370.1067*
H16L0.164530.541700.502040.1067*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0925 (17)0.0424 (12)0.0558 (13)0.0037 (12)−0.0115 (12)−0.0051 (10)
O14A0.0919 (17)0.0440 (13)0.0659 (15)0.0055 (12)−0.0055 (13)0.0048 (11)
N12A0.0678 (16)0.0357 (13)0.0558 (15)−0.0036 (12)−0.0037 (13)−0.0022 (12)
C1A0.0589 (16)0.0435 (17)0.0501 (16)−0.0022 (13)0.0027 (13)−0.0027 (13)
C2A0.0631 (16)0.0359 (15)0.0588 (17)−0.0010 (13)0.0079 (14)−0.0042 (14)
C3A0.079 (2)0.0380 (16)0.0599 (18)−0.0063 (15)0.0023 (16)−0.0087 (14)
C4A0.073 (2)0.0481 (18)0.0528 (17)−0.0078 (15)−0.0025 (15)−0.0088 (14)
C5A0.0569 (16)0.0431 (16)0.0533 (16)−0.0026 (13)0.0015 (13)−0.0009 (14)
C6A0.0533 (15)0.0473 (17)0.0563 (17)−0.0026 (13)0.0038 (13)−0.0022 (14)
C7A0.0642 (18)0.061 (2)0.0595 (19)−0.0020 (16)−0.0044 (15)0.0045 (16)
C8A0.072 (2)0.070 (2)0.067 (2)0.0025 (18)−0.0035 (17)0.018 (2)
C9A0.073 (2)0.0476 (19)0.079 (2)0.0039 (16)0.0060 (18)0.0154 (18)
C10A0.0602 (17)0.0414 (16)0.0667 (19)−0.0010 (13)0.0070 (15)0.0038 (14)
C11A0.0551 (16)0.0438 (16)0.0580 (17)−0.0044 (13)0.0060 (14)0.0028 (14)
C13A0.0567 (16)0.0349 (15)0.0551 (16)−0.0010 (12)0.0015 (13)−0.0044 (12)
C14A0.0674 (18)0.0377 (16)0.069 (2)0.0005 (14)0.0101 (16)0.0019 (15)
C15A0.095 (3)0.0365 (16)0.080 (3)0.0020 (17)0.000 (2)−0.0004 (17)
C16A0.090 (3)0.0424 (18)0.085 (3)−0.0042 (17)0.002 (2)−0.0031 (17)
O1B0.0975 (17)0.0459 (13)0.0545 (13)0.0059 (12)0.0058 (12)0.0019 (11)
O14B0.1069 (19)0.0479 (14)0.0619 (15)0.0055 (13)0.0038 (14)0.0116 (12)
N12B0.0711 (16)0.0403 (14)0.0672 (18)0.0040 (12)−0.0050 (14)0.0053 (13)
C1B0.0559 (16)0.0400 (16)0.0539 (16)−0.0020 (12)−0.0024 (13)0.0037 (13)
C2B0.0569 (16)0.0369 (14)0.0579 (16)−0.0031 (12)−0.0019 (13)0.0026 (13)
C3B0.0662 (18)0.0492 (17)0.0616 (18)0.0019 (15)0.0016 (15)−0.0046 (15)
C4B0.0716 (19)0.0554 (19)0.0562 (18)−0.0022 (16)0.0005 (15)0.0024 (15)
C5B0.0555 (16)0.0513 (17)0.0559 (17)−0.0055 (14)−0.0041 (13)0.0049 (14)
C6B0.0583 (17)0.0557 (19)0.063 (2)−0.0048 (15)−0.0087 (14)0.0137 (16)
C7B0.074 (2)0.074 (2)0.068 (2)−0.0086 (19)−0.0062 (18)0.0169 (19)
C8B0.096 (3)0.076 (3)0.078 (3)−0.007 (2)−0.012 (2)0.035 (2)
C9B0.087 (2)0.058 (2)0.098 (3)−0.0015 (19)−0.024 (2)0.033 (2)
C10B0.072 (2)0.0476 (18)0.089 (3)0.0035 (16)−0.0194 (19)0.0149 (19)
C11B0.0578 (17)0.0480 (18)0.072 (2)−0.0015 (14)−0.0118 (15)0.0138 (16)
C13B0.0530 (15)0.0395 (15)0.0613 (17)−0.0038 (12)−0.0072 (13)0.0028 (13)
C14B0.0619 (18)0.0439 (17)0.070 (2)−0.0022 (14)−0.0014 (15)0.0033 (15)
C15B0.115 (3)0.0445 (19)0.081 (3)0.012 (2)0.014 (2)0.0106 (18)
C16B0.110 (3)0.062 (3)0.099 (3)0.022 (2)−0.004 (3)0.014 (2)
O1C0.112 (2)0.0433 (13)0.0614 (15)−0.0050 (13)−0.0314 (14)0.0027 (11)
O14C0.1079 (19)0.0457 (14)0.0645 (15)0.0020 (13)−0.0148 (14)0.0041 (12)
N12C0.0740 (17)0.0421 (14)0.0523 (15)−0.0021 (12)−0.0112 (13)−0.0014 (12)
C1C0.0671 (18)0.0423 (16)0.0506 (16)0.0012 (14)−0.0081 (14)−0.0005 (13)
C2C0.0637 (17)0.0391 (15)0.0558 (17)−0.0013 (13)0.0004 (14)−0.0009 (13)
C3C0.0660 (18)0.0427 (16)0.0590 (17)−0.0055 (14)−0.0050 (14)−0.0075 (14)
C4C0.0606 (17)0.0520 (19)0.0553 (17)−0.0046 (14)−0.0082 (14)−0.0069 (14)
C5C0.0527 (15)0.0473 (16)0.0513 (15)0.0036 (13)−0.0029 (12)0.0002 (14)
C6C0.0574 (16)0.0464 (16)0.0534 (16)0.0048 (13)0.0003 (13)0.0005 (13)
C7C0.0684 (19)0.060 (2)0.0549 (17)0.0084 (16)−0.0056 (15)0.0016 (16)
C8C0.078 (2)0.067 (2)0.0572 (19)0.0114 (18)−0.0072 (16)0.0076 (17)
C9C0.089 (2)0.0486 (19)0.066 (2)0.0113 (17)0.0049 (18)0.0114 (16)
C10C0.076 (2)0.0431 (17)0.0596 (18)0.0022 (15)0.0000 (16)0.0030 (14)
C11C0.0625 (17)0.0451 (16)0.0507 (16)0.0021 (13)0.0004 (14)−0.0005 (13)
C13C0.0589 (16)0.0415 (15)0.0525 (16)−0.0026 (13)−0.0043 (13)−0.0023 (13)
C14C0.077 (2)0.0389 (16)0.0619 (19)0.0022 (15)0.0020 (16)0.0004 (14)
C15C0.105 (3)0.0430 (19)0.094 (3)−0.0040 (19)−0.020 (2)0.0043 (19)
C16C0.115 (3)0.045 (2)0.084 (3)−0.010 (2)−0.015 (2)0.0025 (19)
O1D0.1049 (19)0.0458 (13)0.0533 (13)−0.0008 (12)−0.0209 (12)0.0007 (11)
O14D0.1045 (19)0.0544 (15)0.0636 (15)0.0026 (14)−0.0161 (14)0.0079 (12)
N12D0.0693 (16)0.0384 (13)0.0497 (14)0.0044 (11)−0.0058 (12)0.0004 (11)
C1D0.0621 (16)0.0423 (16)0.0498 (16)0.0015 (14)−0.0055 (13)0.0004 (13)
C2D0.0629 (17)0.0400 (16)0.0536 (17)0.0048 (13)0.0008 (14)0.0001 (13)
C3D0.076 (2)0.0411 (16)0.0593 (19)0.0040 (15)−0.0055 (16)−0.0090 (14)
C4D0.079 (2)0.0535 (19)0.0475 (16)0.0047 (16)−0.0050 (15)−0.0059 (14)
C5D0.0627 (16)0.0461 (17)0.0445 (14)0.0053 (14)−0.0011 (12)0.0020 (13)
C6D0.0656 (18)0.0458 (17)0.0522 (16)0.0069 (14)0.0043 (14)−0.0008 (14)
C7D0.091 (2)0.058 (2)0.0502 (17)0.0066 (18)−0.0041 (16)0.0043 (16)
C8D0.095 (3)0.065 (2)0.061 (2)0.012 (2)−0.0045 (19)0.0141 (18)
C9D0.090 (2)0.0450 (18)0.069 (2)0.0080 (17)0.0036 (19)0.0141 (16)
C10D0.0672 (19)0.0424 (17)0.0641 (19)0.0039 (14)0.0025 (15)0.0056 (14)
C11D0.0597 (17)0.0443 (17)0.0516 (17)0.0050 (13)0.0020 (13)0.0028 (13)
C13D0.0580 (15)0.0395 (15)0.0506 (15)0.0021 (13)0.0004 (12)−0.0021 (13)
C14D0.0645 (17)0.0412 (17)0.064 (2)0.0016 (14)0.0003 (15)0.0054 (14)
C15D0.091 (2)0.0459 (19)0.073 (2)0.0061 (17)−0.0031 (19)0.0020 (17)
C16D0.089 (3)0.0414 (18)0.083 (3)−0.0008 (17)−0.004 (2)0.0021 (17)
Geometric parameters (Å, º) top
O1A—C1A1.344 (4)C14B—C15B1.493 (6)
O14A—C14A1.240 (5)C3B—H3B0.9300
O1A—H1A0.85 (4)C4B—H4B0.9300
O1B—C1B1.342 (4)C7B—H7B0.9300
O14B—C14B1.236 (5)C8B—H8B0.9300
O1B—H1B0.83 (4)C9B—H9B0.9300
O1C—C1C1.344 (4)C15B—H15E0.9600
O14C—C14C1.235 (5)C15B—H15F0.9600
O1C—H1C0.84 (3)C15B—H15D0.9600
O1D—C1D1.343 (4)C16B—H16E0.9600
O14D—C14D1.244 (5)C16B—H16F0.9600
O1D—H1D0.85 (4)C16B—H16D0.9600
N12A—C11A1.382 (5)C1C—C2C1.408 (5)
N12A—C13A1.384 (4)C1C—C13C1.398 (5)
N12A—H12A0.79 (5)C2C—C3C1.426 (5)
N12B—C13B1.382 (4)C2C—C14C1.456 (5)
N12B—C11B1.378 (5)C3C—C4C1.355 (5)
N12B—H12B0.93 (5)C4C—C5C1.407 (5)
N12C—C11C1.383 (4)C5C—C6C1.433 (5)
N12C—C13C1.387 (5)C5C—C13C1.401 (4)
N12C—H12C0.88 (4)C6C—C11C1.409 (5)
N12D—C13D1.386 (4)C6C—C7C1.386 (5)
N12D—C11D1.386 (4)C7C—C8C1.374 (5)
N12D—H12D0.86 (4)C8C—C9C1.390 (5)
C1A—C13A1.400 (5)C9C—C10C1.373 (5)
C1A—C2A1.402 (5)C10C—C11C1.409 (5)
C2A—C14A1.468 (5)C10C—C16C1.496 (6)
C2A—C3A1.419 (5)C14C—C15C1.508 (6)
C3A—C4A1.359 (5)C3C—H3C0.9300
C4A—C5A1.408 (5)C4C—H4C0.9300
C5A—C13A1.402 (5)C7C—H7C0.9300
C5A—C6A1.433 (5)C8C—H8C0.9300
C6A—C11A1.409 (5)C9C—H9C0.9300
C6A—C7A1.398 (5)C15C—H15I0.9600
C7A—C8A1.375 (5)C15C—H15G0.9600
C8A—C9A1.390 (6)C15C—H15H0.9600
C9A—C10A1.385 (5)C16C—H16G0.9600
C10A—C16A1.488 (6)C16C—H16H0.9600
C10A—C11A1.407 (5)C16C—H16I0.9600
C14A—C15A1.507 (5)C1D—C2D1.408 (5)
C3A—H3A0.9300C1D—C13D1.403 (5)
C4A—H4A0.9300C2D—C3D1.421 (5)
C7A—H7A0.9300C2D—C14D1.461 (5)
C8A—H8A0.9300C3D—C4D1.362 (5)
C9A—H9A0.9300C4D—C5D1.409 (5)
C15A—H15A0.9600C5D—C6D1.430 (5)
C15A—H15B0.9600C5D—C13D1.395 (4)
C15A—H15C0.9600C6D—C7D1.404 (5)
C16A—H16A0.9600C6D—C11D1.398 (5)
C16A—H16C0.9600C7D—C8D1.365 (5)
C16A—H16B0.9600C8D—C9D1.399 (6)
C1B—C2B1.403 (4)C9D—C10D1.384 (5)
C1B—C13B1.405 (4)C10D—C11D1.407 (5)
C2B—C14B1.456 (5)C10D—C16D1.478 (6)
C2B—C3B1.433 (5)C14D—C15D1.490 (5)
C3B—C4B1.358 (5)C3D—H3D0.9300
C4B—C5B1.397 (5)C4D—H4D0.9300
C5B—C13B1.400 (5)C7D—H7D0.9300
C5B—C6B1.433 (5)C8D—H8D0.9300
C6B—C11B1.398 (5)C9D—H9D0.9300
C6B—C7B1.406 (5)C15D—H15J0.9600
C7B—C8B1.372 (6)C15D—H15K0.9600
C8B—C9B1.384 (7)C15D—H15L0.9600
C9B—C10B1.383 (7)C16D—H16J0.9600
C10B—C16B1.462 (7)C16D—H16K0.9600
C10B—C11B1.412 (5)C16D—H16L0.9600
O1A···O14A2.563 (3)C14C···H7Bvii2.9300
O1A···N12A2.909 (4)C14D···H16Kiv3.0700
O1B···C13Ai3.386 (4)C14D···H1D2.46 (4)
O1B···O14B2.574 (4)C15A···H16Ax2.8500
O1B···N12B2.904 (4)C15A···H3A2.6100
O1B···C1Ai3.387 (4)C15B···H3B2.6000
O1C···N12C2.898 (4)C15C···H3C2.6100
O1C···C15Dii3.388 (5)C15D···H16Jvii2.8900
O1C···O14C2.575 (4)C15D···H3D2.6100
O1D···O14D2.573 (4)C16A···H12A2.90 (5)
O1D···N12D2.913 (4)C16A···H1Bv3.05 (5)
O14A···C16Biii3.247 (6)C16B···H1Av2.95 (5)
O14A···N12Biii3.176 (4)C16B···H12B2.93 (5)
O14A···O1A2.563 (3)C16C···H12C2.93 (4)
O14B···O1B2.574 (4)C16C···H1Dii2.83 (5)
O14B···N12Aiii3.052 (4)C16D···H1Cii3.02 (5)
O14B···C16Aiii3.317 (5)C16D···H12D2.95 (4)
O14C···N12Div3.105 (4)H1A···H16Fiii2.3300
O14C···C16Div3.361 (5)H1A···H16Cvi2.5800
O14C···O1C2.575 (4)H1A···O14A1.80 (4)
O14D···C16Civ3.204 (5)H1A···C16Biii2.95 (5)
O14D···N12Civ3.133 (4)H1A···C14A2.38 (4)
O14D···O1D2.573 (4)H1B···C16Aiii3.05 (6)
O1A···H12A2.81 (5)H1B···C14B2.42 (5)
O1A···H15Dv2.6000H1B···C2Ai3.08 (6)
O1A···H16Cvi2.8700H1B···O14B1.85 (4)
O1B···H15Av2.4700H1C···H16Kiv2.5700
O1B···H12B2.73 (5)H1C···C16Div3.02 (5)
O1C···H15Jii2.4400H1C···O14C1.79 (3)
O1C···H12C2.75 (4)H1C···C14C2.30 (4)
O1D···H15Iii2.5300H1D···H16Giv2.2700
O1D···H12D2.75 (4)H1D···O14D1.87 (4)
O14A···H1A1.80 (4)H1D···C14D2.46 (4)
O14A···H16Fiii2.7600H1D···C16Civ2.83 (5)
O14A···H12Biii2.33 (5)H3A···C7Cx3.0900
O14A···H16Eiii2.8700H3A···H15C2.4300
O14A···H16Cvi2.7500H3A···C15A2.6100
O14B···H12Aiii2.27 (5)H3A···H15B2.4200
O14B···H16Biii2.7800H3B···H15E2.5400
O14B···H1B1.85 (4)H3B···C15B2.6000
O14C···H7Bvii2.8800H3B···H15F2.2700
O14C···H12Div2.26 (4)H3C···H15H2.4400
O14C···H1C1.79 (3)H3C···H15G2.3900
O14C···H16Kiv2.7700H3C···C15C2.6100
O14D···H16Giv2.7700H3D···C15D2.6100
O14D···H1D1.87 (4)H3D···H15K2.4000
O14D···H12Civ2.28 (4)H3D···H15L2.4500
O14D···H16Iiv2.7800H4B···H7Dxi2.5100
N12A···O14Bv3.052 (4)H4B···C1Cx2.8300
N12A···O1A2.909 (4)H4B···C13Cx2.9200
N12B···C7A3.377 (5)H4C···C5Bxii2.9100
N12B···O14Av3.176 (4)H4C···C13Bxii2.9600
N12B···O1B2.904 (4)H4D···H7Bxii2.4800
N12C···O1C2.898 (4)H7A···C13B2.9500
N12C···O14Dii3.133 (4)H7B···C14Cx2.9300
N12D···O14Cii3.105 (4)H7B···H4Dxi2.4800
N12D···O1D2.913 (4)H7B···O14Cx2.8800
N12A···H15Bv2.9000H7C···C3Avii3.0000
N12B···H16E2.8700H7C···C4Avii3.0600
N12C···H16I2.9200H7C···C2Bxii2.9800
N12D···H16K2.9500H7D···H4Bxii2.5100
N12D···H15Lviii2.7800H7D···C4Bxii2.9900
C1A···O1Bix3.387 (4)H8A···C10B3.0900
C1C···C4D3.474 (5)H8C···H16Dix2.5300
C1C···C4Bvii3.496 (5)H8D···H9Bix2.4900
C2A···C16Aiii3.533 (5)H9A···H16A2.3500
C2C···C4D3.422 (5)H9A···H9C2.5000
C3D···C14C3.460 (5)H9B···H16D2.3500
C4B···C13Cx3.390 (5)H9B···H8Di2.4900
C4B···C4Cxi3.599 (5)H9B···H9Di2.6000
C4B···C1Cx3.496 (5)H9C···H9A2.5000
C4C···C4Bxii3.599 (5)H9C···H16H2.3800
C4C···C5Bxii3.416 (4)H9C···C9A3.0200
C4D···C2C3.422 (5)H9D···H16J2.3500
C4D···C1C3.474 (5)H9D···H9Bix2.6000
C5B···C4Cxi3.416 (4)H12A···C16A2.90 (5)
C6C···C7D3.567 (5)H12A···O14Bv2.27 (5)
C7A···N12B3.377 (5)H12A···O1A2.81 (5)
C7A···C13B3.484 (5)H12B···C16B2.93 (5)
C7B···C14Cx3.405 (5)H12B···H16E2.5800
C7D···C6C3.567 (5)H12B···O14Av2.33 (5)
C7D···C13C3.595 (5)H12B···O1B2.73 (5)
C7D···C11C3.497 (5)H12C···O1C2.75 (4)
C8A···C11B3.555 (5)H12C···O14Dii2.28 (4)
C8D···C11C3.432 (5)H12C···C16C2.93 (4)
C8D···C10C3.554 (6)H12D···C16D2.95 (4)
C10A···C14Av3.593 (5)H12D···O1D2.75 (4)
C10C···C8D3.554 (6)H12D···O14Cii2.26 (4)
C10D···C14Dviii3.594 (5)H15A···O1Biii2.4700
C11B···C8A3.555 (5)H15B···H3A2.4200
C11C···C8D3.432 (5)H15B···C3A2.9100
C11C···C7D3.497 (5)H15B···C11Aiii3.0300
C11D···C15Dviii3.582 (5)H15B···H16Ax2.5100
C11D···C14Dviii3.555 (5)H15B···N12Aiii2.9000
C13A···O1Bix3.386 (4)H15C···C3A2.9200
C13B···C7A3.484 (5)H15C···H3A2.4300
C13C···C4Bvii3.390 (5)H15D···O1Aiii2.6000
C13C···C7D3.595 (5)H15E···H3B2.5400
C14A···C10Aiii3.593 (5)H15E···C3B3.0200
C14C···C3D3.460 (5)H15F···C9Cx3.0100
C14C···C7Bvii3.405 (5)H15F···C3B2.7600
C14D···C10Dxiii3.594 (5)H15F···C7Cx3.1000
C14D···C11Dxiii3.555 (5)H15F···C8Cx2.9900
C15A···C16Ax3.533 (5)H15F···H3B2.2700
C15D···C11Dxiii3.582 (5)H15G···H3C2.3900
C15D···O1Civ3.388 (5)H15G···C3C2.8900
C15D···C16Dvii3.548 (5)H15G···H16Hvii2.5600
C16A···C15Avii3.533 (5)H15H···C3C2.9200
C16A···C2Av3.533 (5)H15H···H3C2.4400
C16A···O14Bv3.317 (5)H15H···C8Bxii2.9800
C16B···O14Av3.247 (6)H15I···O1Div2.5300
C16C···O14Dii3.204 (5)H15J···O1Civ2.4400
C16D···O14Cii3.361 (5)H15K···C3D2.8700
C16D···C15Dx3.548 (5)H15K···H3D2.4000
C1C···H4Bvii2.8300H15L···H3D2.4500
C2A···H1Bix3.08 (6)H15L···C3D2.9500
C2A···H16Biii2.9000H15L···C11Dxiii2.9000
C2B···H7Cxi2.9800H15L···N12Dxiii2.7800
C2D···H16Lxiii2.9200H15L···C13Dxiii2.9300
C3A···H7Cx3.0000H16A···H15Bvii2.5100
C3A···H15C2.9200H16A···C15Avii2.8500
C3A···H15B2.9100H16A···H9A2.3500
C3A···H16Biii2.8600H16B···C2Av2.9000
C3B···H15E3.0200H16B···O14Bv2.7800
C3B···H15F2.7600H16B···C3Av2.8600
C3C···H15H2.9200H16C···O1Axiv2.8700
C3C···H15G2.8900H16C···O14Axiv2.7500
C3D···H15K2.8700H16C···H1Axiv2.5800
C3D···H16Lxiii2.8500H16D···H8Ci2.5300
C3D···H15L2.9500H16D···H9B2.3500
C4A···H7Cx3.0600H16D···C9Ci2.9500
C4B···H7Dxi2.9900H16D···C8Ci2.8900
C5B···H4Cxi2.9100H16E···H12B2.5800
C7C···H15Fvii3.1000H16E···N12B2.8700
C7C···H3Avii3.0900H16E···C9Ai2.9600
C8B···H15Hxi2.9800H16E···O14Av2.8700
C8C···H15Fvii2.9900H16F···H1Av2.3300
C8C···H16Dix2.8900H16F···O14Av2.7600
C9A···H16Eix2.9600H16G···C9D3.0400
C9A···H9C3.0200H16G···O14Dii2.7700
C9C···H15Fvii3.0100H16G···H1Dii2.2700
C9C···H16Dix2.9500H16H···H9C2.3800
C9D···H16G3.0400H16H···H15Gx2.5600
C10B···H8A3.0900H16I···N12C2.9200
C11A···H15Bv3.0300H16I···O14Dii2.7800
C11D···H15Lviii2.9000H16J···C15Dx2.8900
C13B···H4Cxi2.9600H16J···H9D2.3500
C13B···H7A2.9500H16K···N12D2.9500
C13C···H4Bvii2.9200H16K···O14Cii2.7700
C13D···H15Lviii2.9300H16K···C14Dii3.0700
C14A···H1A2.38 (4)H16K···H1Cii2.5700
C14B···H1B2.42 (5)H16L···C2Dviii2.9200
C14C···H1C2.30 (4)H16L···C3Dviii2.8500
C1A—O1A—H1A108 (3)H15D—C15B—H15E110.00
C1B—O1B—H1B108 (3)H15E—C15B—H15F109.00
C1C—O1C—H1C99 (4)H16D—C16B—H16E109.00
C1D—O1D—H1D113 (3)C10B—C16B—H16E110.00
C11A—N12A—C13A108.0 (3)H16D—C16B—H16F109.00
C11A—N12A—H12A124 (4)C10B—C16B—H16F110.00
C13A—N12A—H12A128 (4)C10B—C16B—H16D110.00
C11B—N12B—C13B107.2 (3)H16E—C16B—H16F109.00
C13B—N12B—H12B123 (3)C2C—C1C—C13C118.2 (3)
C11B—N12B—H12B130 (3)O1C—C1C—C2C123.6 (3)
C11C—N12C—C13C107.9 (3)O1C—C1C—C13C118.2 (3)
C13C—N12C—H12C125 (2)C1C—C2C—C14C119.5 (3)
C11C—N12C—H12C127 (2)C3C—C2C—C14C121.7 (3)
C11D—N12D—C13D107.8 (3)C1C—C2C—C3C118.8 (3)
C13D—N12D—H12D124 (3)C2C—C3C—C4C122.6 (3)
C11D—N12D—H12D128 (3)C3C—C4C—C5C118.9 (3)
O1A—C1A—C2A123.3 (3)C4C—C5C—C13C119.7 (3)
C2A—C1A—C13A118.0 (3)C6C—C5C—C13C106.6 (3)
O1A—C1A—C13A118.7 (3)C4C—C5C—C6C133.7 (3)
C1A—C2A—C3A119.5 (3)C5C—C6C—C11C106.8 (3)
C3A—C2A—C14A121.3 (3)C7C—C6C—C11C119.9 (3)
C1A—C2A—C14A119.2 (3)C5C—C6C—C7C133.4 (3)
C2A—C3A—C4A122.2 (3)C6C—C7C—C8C118.9 (3)
C3A—C4A—C5A119.0 (3)C7C—C8C—C9C120.4 (3)
C4A—C5A—C6A134.1 (3)C8C—C9C—C10C123.3 (4)
C6A—C5A—C13A106.4 (3)C11C—C10C—C16C121.4 (3)
C4A—C5A—C13A119.5 (3)C9C—C10C—C11C115.9 (3)
C7A—C6A—C11A119.8 (3)C9C—C10C—C16C122.7 (3)
C5A—C6A—C11A106.9 (3)N12C—C11C—C6C109.2 (3)
C5A—C6A—C7A133.2 (3)C6C—C11C—C10C121.6 (3)
C6A—C7A—C8A118.5 (4)N12C—C11C—C10C129.2 (3)
C7A—C8A—C9A120.9 (4)N12C—C13C—C1C128.5 (3)
C8A—C9A—C10A122.9 (4)C1C—C13C—C5C121.9 (3)
C11A—C10A—C16A122.3 (3)N12C—C13C—C5C109.6 (3)
C9A—C10A—C11A115.8 (3)C2C—C14C—C15C120.2 (3)
C9A—C10A—C16A121.9 (3)O14C—C14C—C2C121.2 (3)
C6A—C11A—C10A122.0 (3)O14C—C14C—C15C118.6 (3)
N12A—C11A—C6A109.0 (3)C2C—C3C—H3C119.00
N12A—C11A—C10A129.0 (3)C4C—C3C—H3C119.00
C1A—C13A—C5A121.8 (3)C5C—C4C—H4C121.00
N12A—C13A—C5A109.7 (3)C3C—C4C—H4C121.00
N12A—C13A—C1A128.5 (3)C6C—C7C—H7C121.00
C2A—C14A—C15A120.6 (3)C8C—C7C—H7C121.00
O14A—C14A—C2A121.2 (3)C7C—C8C—H8C120.00
O14A—C14A—C15A118.2 (3)C9C—C8C—H8C120.00
C2A—C3A—H3A119.00C8C—C9C—H9C118.00
C4A—C3A—H3A119.00C10C—C9C—H9C118.00
C5A—C4A—H4A121.00C14C—C15C—H15H109.00
C3A—C4A—H4A120.00C14C—C15C—H15I109.00
C6A—C7A—H7A121.00H15G—C15C—H15H109.00
C8A—C7A—H7A121.00C14C—C15C—H15G109.00
C7A—C8A—H8A120.00H15G—C15C—H15I109.00
C9A—C8A—H8A119.00H15H—C15C—H15I109.00
C10A—C9A—H9A119.00H16G—C16C—H16I109.00
C8A—C9A—H9A119.00C10C—C16C—H16I109.00
C14A—C15A—H15C109.00H16G—C16C—H16H110.00
H15B—C15A—H15C109.00C10C—C16C—H16G109.00
C14A—C15A—H15B109.00C10C—C16C—H16H109.00
C14A—C15A—H15A109.00H16H—C16C—H16I109.00
H15A—C15A—H15C110.00C2D—C1D—C13D118.1 (3)
H15A—C15A—H15B110.00O1D—C1D—C2D123.4 (3)
H16A—C16A—H16B109.00O1D—C1D—C13D118.5 (3)
C10A—C16A—H16C109.00C1D—C2D—C3D119.1 (3)
C10A—C16A—H16B109.00C1D—C2D—C14D119.5 (3)
H16A—C16A—H16C109.00C3D—C2D—C14D121.4 (3)
H16B—C16A—H16C109.00C2D—C3D—C4D122.4 (3)
C10A—C16A—H16A109.00C3D—C4D—C5D118.7 (3)
C2B—C1B—C13B118.5 (3)C6D—C5D—C13D106.5 (3)
O1B—C1B—C13B117.8 (3)C4D—C5D—C6D133.5 (3)
O1B—C1B—C2B123.7 (3)C4D—C5D—C13D120.0 (3)
C1B—C2B—C3B119.0 (3)C5D—C6D—C7D132.9 (3)
C3B—C2B—C14B121.1 (3)C5D—C6D—C11D107.2 (3)
C1B—C2B—C14B119.9 (3)C7D—C6D—C11D119.9 (3)
C2B—C3B—C4B121.8 (3)C6D—C7D—C8D118.6 (3)
C3B—C4B—C5B119.3 (3)C7D—C8D—C9D120.4 (4)
C6B—C5B—C13B106.3 (3)C8D—C9D—C10D123.5 (4)
C4B—C5B—C13B120.4 (3)C9D—C10D—C16D122.3 (3)
C4B—C5B—C6B133.3 (3)C9D—C10D—C11D115.1 (3)
C5B—C6B—C11B106.4 (3)C11D—C10D—C16D122.6 (3)
C5B—C6B—C7B133.2 (3)N12D—C11D—C6D109.0 (3)
C7B—C6B—C11B120.4 (3)N12D—C11D—C10D128.5 (3)
C6B—C7B—C8B118.0 (4)C6D—C11D—C10D122.5 (3)
C7B—C8B—C9B121.2 (4)C1D—C13D—C5D121.7 (3)
C8B—C9B—C10B122.8 (4)N12D—C13D—C1D128.8 (3)
C11B—C10B—C16B121.3 (4)N12D—C13D—C5D109.6 (3)
C9B—C10B—C11B116.3 (4)O14D—C14D—C2D121.0 (3)
C9B—C10B—C16B122.4 (4)O14D—C14D—C15D118.0 (3)
C6B—C11B—C10B121.3 (4)C2D—C14D—C15D120.9 (3)
N12B—C11B—C10B128.5 (4)C2D—C3D—H3D119.00
N12B—C11B—C6B110.1 (3)C4D—C3D—H3D119.00
N12B—C13B—C5B110.0 (3)C3D—C4D—H4D121.00
N12B—C13B—C1B129.0 (3)C5D—C4D—H4D121.00
C1B—C13B—C5B121.0 (3)C6D—C7D—H7D121.00
C2B—C14B—C15B120.2 (3)C8D—C7D—H7D121.00
O14B—C14B—C15B119.3 (3)C7D—C8D—H8D120.00
O14B—C14B—C2B120.5 (3)C9D—C8D—H8D120.00
C2B—C3B—H3B119.00C8D—C9D—H9D118.00
C4B—C3B—H3B119.00C10D—C9D—H9D118.00
C3B—C4B—H4B120.00C14D—C15D—H15J109.00
C5B—C4B—H4B120.00C14D—C15D—H15K109.00
C8B—C7B—H7B121.00C14D—C15D—H15L109.00
C6B—C7B—H7B121.00H15J—C15D—H15K110.00
C7B—C8B—H8B119.00H15J—C15D—H15L110.00
C9B—C8B—H8B119.00H15K—C15D—H15L110.00
C10B—C9B—H9B119.00C10D—C16D—H16J109.00
C8B—C9B—H9B119.00C10D—C16D—H16K109.00
C14B—C15B—H15E109.00C10D—C16D—H16L109.00
C14B—C15B—H15F109.00H16J—C16D—H16K109.00
C14B—C15B—H15D109.00H16J—C16D—H16L109.00
H15D—C15B—H15F109.00H16K—C16D—H16L109.00
C13A—N12A—C11A—C6A−0.4 (4)C6B—C7B—C8B—C9B−0.5 (6)
C13A—N12A—C11A—C10A−179.8 (3)C7B—C8B—C9B—C10B0.5 (7)
C11A—N12A—C13A—C1A−179.2 (3)C8B—C9B—C10B—C16B−176.8 (4)
C11A—N12A—C13A—C5A0.9 (4)C8B—C9B—C10B—C11B0.9 (6)
C11B—N12B—C13B—C1B179.8 (3)C9B—C10B—C11B—N12B180.0 (4)
C13B—N12B—C11B—C6B−0.9 (4)C16B—C10B—C11B—C6B175.4 (4)
C13B—N12B—C11B—C10B177.1 (4)C16B—C10B—C11B—N12B−2.3 (6)
C11B—N12B—C13B—C5B0.9 (4)C9B—C10B—C11B—C6B−2.3 (5)
C11C—N12C—C13C—C5C0.9 (4)O1C—C1C—C2C—C3C−178.4 (3)
C13C—N12C—C11C—C10C179.1 (3)O1C—C1C—C13C—C5C178.9 (3)
C11C—N12C—C13C—C1C178.4 (3)C2C—C1C—C13C—N12C−177.6 (3)
C13C—N12C—C11C—C6C−0.3 (4)C2C—C1C—C13C—C5C−0.4 (5)
C11D—N12D—C13D—C1D178.9 (3)O1C—C1C—C2C—C14C1.4 (5)
C13D—N12D—C11D—C10D−177.9 (3)C13C—C1C—C2C—C3C0.9 (4)
C13D—N12D—C11D—C6D1.1 (4)C13C—C1C—C2C—C14C−179.3 (3)
C11D—N12D—C13D—C5D−1.1 (4)O1C—C1C—C13C—N12C1.7 (5)
O1A—C1A—C13A—N12A0.2 (5)C3C—C2C—C14C—O14C178.4 (3)
C13A—C1A—C2A—C14A179.8 (3)C3C—C2C—C14C—C15C−1.8 (5)
C2A—C1A—C13A—N12A−180.0 (3)C1C—C2C—C3C—C4C−1.1 (5)
C2A—C1A—C13A—C5A−0.2 (5)C14C—C2C—C3C—C4C179.1 (3)
O1A—C1A—C13A—C5A−179.9 (3)C1C—C2C—C14C—O14C−1.4 (5)
C13A—C1A—C2A—C3A0.4 (5)C1C—C2C—C14C—C15C178.4 (3)
O1A—C1A—C2A—C3A−179.8 (3)C2C—C3C—C4C—C5C0.8 (5)
O1A—C1A—C2A—C14A−0.5 (5)C3C—C4C—C5C—C6C178.3 (3)
C3A—C2A—C14A—O14A−178.6 (3)C3C—C4C—C5C—C13C−0.4 (5)
C1A—C2A—C3A—C4A−0.7 (5)C4C—C5C—C13C—N12C177.8 (3)
C14A—C2A—C3A—C4A180.0 (3)C4C—C5C—C13C—C1C0.2 (5)
C1A—C2A—C14A—O14A2.1 (5)C6C—C5C—C13C—N12C−1.2 (4)
C3A—C2A—C14A—C15A1.0 (5)C4C—C5C—C6C—C7C2.5 (6)
C1A—C2A—C14A—C15A−178.3 (3)C4C—C5C—C6C—C11C−177.8 (3)
C2A—C3A—C4A—C5A0.7 (5)C13C—C5C—C6C—C7C−178.7 (4)
C3A—C4A—C5A—C6A−179.0 (4)C13C—C5C—C6C—C11C1.0 (3)
C3A—C4A—C5A—C13A−0.4 (5)C6C—C5C—C13C—C1C−178.8 (3)
C6A—C5A—C13A—N12A−1.0 (3)C5C—C6C—C11C—C10C−179.9 (3)
C13A—C5A—C6A—C7A−179.6 (4)C7C—C6C—C11C—C10C−0.1 (5)
C13A—C5A—C6A—C11A0.8 (3)C11C—C6C—C7C—C8C−0.4 (5)
C4A—C5A—C6A—C7A−0.8 (6)C7C—C6C—C11C—N12C179.3 (3)
C4A—C5A—C6A—C11A179.5 (4)C5C—C6C—C7C—C8C179.4 (3)
C4A—C5A—C13A—C1A0.2 (5)C5C—C6C—C11C—N12C−0.4 (4)
C4A—C5A—C13A—N12A−180.0 (3)C6C—C7C—C8C—C9C0.3 (6)
C6A—C5A—C13A—C1A179.1 (3)C7C—C8C—C9C—C10C0.1 (6)
C5A—C6A—C11A—C10A179.2 (3)C8C—C9C—C10C—C11C−0.6 (5)
C5A—C6A—C11A—N12A−0.2 (4)C8C—C9C—C10C—C16C−179.4 (4)
C7A—C6A—C11A—N12A−180.0 (3)C9C—C10C—C11C—C6C0.5 (5)
C7A—C6A—C11A—C10A−0.5 (5)C16C—C10C—C11C—N12C0.1 (6)
C11A—C6A—C7A—C8A0.7 (5)C16C—C10C—C11C—C6C179.4 (3)
C5A—C6A—C7A—C8A−178.9 (3)C9C—C10C—C11C—N12C−178.8 (3)
C6A—C7A—C8A—C9A0.2 (6)O1D—C1D—C2D—C3D179.1 (3)
C7A—C8A—C9A—C10A−1.5 (6)O1D—C1D—C2D—C14D−3.2 (5)
C8A—C9A—C10A—C11A1.7 (5)C13D—C1D—C2D—C3D−2.4 (4)
C8A—C9A—C10A—C16A−177.3 (4)C13D—C1D—C2D—C14D175.3 (3)
C9A—C10A—C11A—N12A178.7 (3)O1D—C1D—C13D—N12D1.2 (5)
C9A—C10A—C11A—C6A−0.7 (5)O1D—C1D—C13D—C5D−178.9 (3)
C16A—C10A—C11A—C6A178.3 (3)C2D—C1D—C13D—N12D−177.3 (3)
C16A—C10A—C11A—N12A−2.4 (5)C2D—C1D—C13D—C5D2.6 (4)
O1B—C1B—C2B—C3B−179.5 (3)C1D—C2D—C3D—C4D0.4 (5)
C13B—C1B—C2B—C3B1.3 (4)C14D—C2D—C3D—C4D−177.2 (3)
C13B—C1B—C2B—C14B−178.6 (3)C1D—C2D—C14D—O14D3.2 (5)
O1B—C1B—C2B—C14B0.6 (5)C1D—C2D—C14D—C15D−174.6 (3)
O1B—C1B—C13B—N12B0.9 (5)C3D—C2D—C14D—O14D−179.2 (3)
O1B—C1B—C13B—C5B179.7 (3)C3D—C2D—C14D—C15D3.1 (5)
C2B—C1B—C13B—N12B−179.8 (3)C2D—C3D—C4D—C5D1.5 (5)
C2B—C1B—C13B—C5B−1.1 (4)C3D—C4D—C5D—C6D176.7 (3)
C3B—C2B—C14B—O14B175.4 (3)C3D—C4D—C5D—C13D−1.3 (5)
C1B—C2B—C3B—C4B−0.4 (5)C4D—C5D—C6D—C7D1.1 (6)
C14B—C2B—C3B—C4B179.6 (3)C4D—C5D—C6D—C11D−178.3 (3)
C3B—C2B—C14B—C15B−4.0 (5)C13D—C5D—C6D—C7D179.3 (3)
C1B—C2B—C14B—C15B175.9 (3)C13D—C5D—C6D—C11D0.0 (3)
C1B—C2B—C14B—O14B−4.7 (5)C4D—C5D—C13D—N12D179.2 (3)
C2B—C3B—C4B—C5B−0.9 (5)C4D—C5D—C13D—C1D−0.7 (5)
C3B—C4B—C5B—C13B1.2 (5)C6D—C5D—C13D—N12D0.7 (3)
C3B—C4B—C5B—C6B−179.6 (3)C6D—C5D—C13D—C1D−179.3 (3)
C4B—C5B—C6B—C11B−179.2 (4)C5D—C6D—C7D—C8D−179.0 (4)
C6B—C5B—C13B—N12B−0.6 (3)C11D—C6D—C7D—C8D0.3 (5)
C4B—C5B—C6B—C7B0.8 (6)C5D—C6D—C11D—N12D−0.6 (3)
C4B—C5B—C13B—N12B178.8 (3)C5D—C6D—C11D—C10D178.4 (3)
C13B—C5B—C6B—C7B−179.9 (3)C7D—C6D—C11D—N12D179.9 (3)
C13B—C5B—C6B—C11B0.1 (3)C7D—C6D—C11D—C10D−1.1 (5)
C6B—C5B—C13B—C1B−179.6 (3)C6D—C7D—C8D—C9D0.0 (6)
C4B—C5B—C13B—C1B−0.2 (5)C7D—C8D—C9D—C10D0.6 (7)
C5B—C6B—C11B—C10B−177.6 (3)C8D—C9D—C10D—C11D−1.3 (6)
C11B—C6B—C7B—C8B−0.9 (5)C8D—C9D—C10D—C16D178.9 (4)
C5B—C6B—C11B—N12B0.5 (4)C9D—C10D—C11D—N12D−179.7 (3)
C7B—C6B—C11B—N12B−179.5 (3)C9D—C10D—C11D—C6D1.5 (5)
C7B—C6B—C11B—C10B2.3 (5)C16D—C10D—C11D—N12D0.1 (6)
C5B—C6B—C7B—C8B179.1 (4)C16D—C10D—C11D—C6D−178.7 (3)
Symmetry codes: (i) x+1, y, z; (ii) −x+1, y+1/2, −z+1; (iii) −x+1, y+1/2, −z; (iv) −x+1, y−1/2, −z+1; (v) −x+1, y−1/2, −z; (vi) −x, y+1/2, −z; (vii) x, y−1, z; (viii) −x, y+1/2, −z+1; (ix) x−1, y, z; (x) x, y+1, z; (xi) x+1, y+1, z; (xii) x−1, y−1, z; (xiii) −x, y−1/2, −z+1; (xiv) −x, y−1/2, −z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1A—H1A···O14A0.85 (4)1.80 (4)2.563 (3)147 (5)
O1B—H1B···O14B0.83 (4)1.85 (4)2.574 (4)145 (5)
O1C—H1C···O14C0.84 (3)1.79 (3)2.575 (4)156 (5)
O1D—H1D···O14D0.85 (4)1.87 (4)2.573 (4)139 (5)
N12A—H12A···O14Bv0.79 (5)2.27 (5)3.052 (4)172 (5)
N12B—H12B···O14Av0.93 (5)2.33 (5)3.176 (4)153 (5)
N12C—H12C···O14Dii0.88 (4)2.28 (4)3.133 (4)163 (3)
N12D—H12D···O14Cii0.86 (4)2.26 (4)3.105 (4)168 (3)
C15A—H15A···O1Biii0.962.473.422 (5)173
C15B—H15D···O1Aiii0.962.603.433 (5)145
C15C—H15I···O1Div0.962.533.445 (5)160
C15D—H15J···O1Civ0.962.443.388 (5)170
Symmetry codes: (ii) −x+1, y+1/2, −z+1; (iii) −x+1, y+1/2, −z; (iv) −x+1, y−1/2, −z+1; (v) −x+1, y−1/2, −z.

Experimental details

Crystal data
Chemical formulaC15H13NO2
Mr239.26
Crystal system, space groupMonoclinic, P21
Temperature (K)295
a, b, c (Å)7.4602 (2), 12.7353 (3), 24.9325 (5)
β (°) 92.319 (2)
V (Å3)2366.84 (10)
Z8
Radiation typeCu Kα
µ (mm−1)0.72
Crystal size (mm)0.47 × 0.31 × 0.11
Data collection
DiffractometerOxford Diffraction Xcalibur Ruby Gemini
Absorption correctionMulti-scan
(CrysAlis PRO; Oxford Diffraction, 2010)
Tmin, Tmax0.746, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections		4770, 4770, 4075
Rint0.000
(sin θ/λ)max (Å−1)0.619
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.122, 1.05
No. of reflections4770
No. of parameters685
No. of restraints5
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.16, −0.18

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1A—H1A···O14A0.85 (4)1.80 (4)2.563 (3)147 (5)
O1B—H1B···O14B0.83 (4)1.85 (4)2.574 (4)145 (5)
O1C—H1C···O14C0.84 (3)1.79 (3)2.575 (4)156 (5)
O1D—H1D···O14D0.85 (4)1.87 (4)2.573 (4)139 (5)
N12A—H12A···O14Bi0.79 (5)2.27 (5)3.052 (4)172 (5)
N12B—H12B···O14Ai0.93 (5)2.33 (5)3.176 (4)153 (5)
N12C—H12C···O14Dii0.88 (4)2.28 (4)3.133 (4)163 (3)
N12D—H12D···O14Cii0.86 (4)2.26 (4)3.105 (4)168 (3)
C15A—H15A···O1Biii0.962.473.422 (5)173
C15B—H15D···O1Aiii0.962.603.433 (5)145
C15C—H15I···O1Div0.962.533.445 (5)160
C15D—H15J···O1Civ0.962.443.388 (5)170
Symmetry codes: (i) −x+1, y−1/2, −z; (ii) −x+1, y+1/2, −z+1; (iii) −x+1, y+1/2, −z; (iv) −x+1, y−1/2, −z+1.
 

Acknowledgements

RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase an X-ray diffractometer.

References

First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
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 First citationOxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.  Google Scholar
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 First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationTovey, S. C., Longland, C. L., Mezna, M. & Michelangeli, F. (1998). Eur. J. Pharm. 354, 245–251.  CrossRef CAS Google Scholar
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 First citationVandana, T., Prasad, K. J. R. & Sowmithran, D. (2004). Indian J. Chem. Sect. B, 43, 2405–2409.  Google Scholar

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ISSN: 2056-9890
Volume 66| Part 12| December 2010| Page o3146
https://doi.org/10.1107/S1600536810045769
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