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Acta Cryst. (2009). E65, o740    [ doi:10.1107/S1600536809007983 ]

N-[(2-Hydroxy-1-naphthyl)(2-hydroxyphenyl)methyl]acetamide

M. NizamMohideen, S. Thenmozhi, A. SubbiahPandi, N. P. Selvam and P. T. Perumal

Abstract top

In the asymmetric unit of the title compound, C19H17NO3, there are two crystallographically independent molecules, which are connected to each other by O-H...O hydrogen bonds, forming molecular chains as well as cyclic centrosymmetric R22(16) dimers.

Comment top

β-Acetamido ketones serve as potential intermediates in the synthesis of natural products and antibiotics (Wabnitz & Spencer, 2002). Due to the nucleophilic nature of benzylic hydroxyl groups these are usually protected during multi-step organic synthesis (Barker et al., 2008). Amide moiety and their metal ion complexes are widely used for their properties and potential applications (Gade, 2002; Valeur & Leray, 2000; Linton & Hamilton, 1997). The amide linkage [–NHC(O)-] is known to be strong enough to form and maintain protein architectures and has been utilized to create various molecular devices for a spectrum of purposes in organic chemistry. The effect of substituents on the solid state structures of N-aromatic amides have been described in the literature (Gowda et al., 2000, 2006, 2007). As part of our investigations on acetamide derivatives, the title compound, (I), has been prepared and its crystal structure is presented here.

Figs. 1 and 2 show the molecular structures and conformations of the two crystallographically independent molecules, A (C1—C19, N1, O1, O2, O3) and B (C1A—C19A, N1A, O1A, O2A, O3A), in the asymmetric unit of (I), with the atomic numbering scheme. The bond lengths and angles in the two independent molecules agree with each other. The normal probability plot analyses (International Tables for X-ray Crystallography, 1974, Vol. IV, pp. 293–309) for both bond lengths and angles show that the differences between the two symmetry independent molecules are of a statistical nature. The bond distances of C18 = O3 and C18A = O3A [1.245 (2) and 1.244 (2) Å] for the molecules A and B, respectively, which are typical for double bonds (Fun et al., 2008).

In the molecules A and B, benzene and naphthalene rings are individually planar as expected. The deviations of the atoms O2 and O2A from the least-squares plane of the naphthalene rings are -0.075 (1) and 0.164 (1) Å. The deviations of the atoms O1 and O1A from the least-squares plane of the benzene rings are 0.056 (1) and 0.021 (1) Å. The dihedral angles between the naphthalene ring system and benzene rings are 75.7 (1) and 82.9 (1)° for molecules A and B respectively, and those between the fused rings are 0.3 (1) and 2.8 (1) °.

The crystal packing is stabilized by strong O—H···O inter and intramolecular hydrogen bonds and each molecule has a week intramolecular C—H···O interaction (Table 1). Considering only A-type molecules, atom O1 acts as a donar in a strong intermolecular O—H···O interaction via H1 with acetamido atom O3 of a symmetry related molecule, generating centrosymmetric hydrogen bonded dimers with a cyclic R22(16) ring system (Bernstein et al., 1995) (Fig. 3). The interlinking of A and B molecules via strong O—H···O hydrogen bond generates infinite chains running along c axis. The atoms O3 and O3a act as a acceptors for all inter and intramolecular interactions.

Related literature top

For background literature, see: Barker et al. (2008); Gade (2002); Linton & Hamilton (1997); Valeur & Leray (2000); Wabnitz & Spencer (2002). For related structures, see: Gowda et al. (2000, 2006, 2007). For hydrogen-bond motifs, see: Bernstein et al. (1995). For bond-length data, see: Fun et al. (2008); [Please revise scheme to show the acetamide group correctly]

Experimental top

A mixture of 2-hydroxybenzaldehyde (10 mmol), β-naphthol (10 mmol) and iodine (0.4 mmol, 4 mol%) were mixed in acetonitrile (5 ml). To the suspension acetyl chloride (2.8 mmol, 0.2 ml) was added and the reaction mixture was stirred at room temperature for 6 h. After the completion of the reaction (as monitored by TLC), saturated sodium thiosulfate solution (5 ml) was added. The precipitated solid was filtered and dried. The dried sample was washed with diethyl ether (2 × 10 ml) and again dried. Single crystals of the title compound suitable for X-ray diffraction were obtained by slow evaporation of a solution in ethanol.

Refinement top

All H atoms were positioned geometrically, with N—H = 0.86, O—H = 0.82 and C—H = 0.93, 0.98 and 0.96 Å, for aromatic, methylene and methyl H-atoms, respectively, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C, N), where x = 1.5 for methyl H, and x = 1.2 for all other H atoms.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. One of the two independent molecules in the asymmetric unit of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. The other independent molecules in the asymmetric unit of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 3] Fig. 3. Part of the crystal structure of (I), showing the R22(16) rings. For the sake of clarity, H atoms not involved in the hydrogen bonding have been omitted for clarity. Hydrogen bonding is shown as dashed lines. [Symmetry codes: (*) -x, -y + 1, -z + 1]
N-[(2-Hydroxy-1-naphthyl)(2-hydroxyphenyl)methyl]acetamide top
Crystal data top
C19H17NO3F(000) = 2592
Mr = 307.34Dx = 1.284 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 6464 reflections
a = 21.286 (5) Åθ = 2.5–25°
b = 17.9288 (4) ŵ = 0.09 mm−1
c = 19.524 (7) ÅT = 293 K
β = 121.428 (1)°Prism, colourless
V = 6358 (3) Å30.20 × 0.16 × 0.16 mm
Z = 16
Data collection top
Bruker Kappa APEXII CCD
diffractometer		6464 independent reflections
Radiation source: fine-focus sealed tube4384 reflections with I > 2σ(I)
graphiteRint = 0.034
ω and φ scansθmax = 26.4°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2004)		h = −26→26
Tmin = 0.980, Tmax = 0.986k = −22→22
33278 measured reflectionsl = −24→23
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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0747P)2 + 2.6626P]
where P = (Fo2 + 2Fc2)/3
6464 reflections(Δ/σ)max = 0.005
417 parametersΔρmax = 0.47 e Å−3
0 restraintsΔρmin = −0.49 e Å−3
Crystal data top
C19H17NO3V = 6358 (3) Å3
Mr = 307.34Z = 16
Monoclinic, C2/cMo Kα radiation
a = 21.286 (5) ŵ = 0.09 mm−1
b = 17.9288 (4) ÅT = 293 K
c = 19.524 (7) Å0.20 × 0.16 × 0.16 mm
β = 121.428 (1)°
Data collection top
Bruker Kappa APEXII CCD
diffractometer		6464 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2004)		4384 reflections with I > 2σ(I)
Tmin = 0.980, Tmax = 0.986Rint = 0.034
33278 measured reflectionsθmax = 26.4°
Refinement top
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.146Δρmax = 0.47 e Å−3
S = 1.02Δρmin = −0.49 e Å−3
6464 reflectionsAbsolute structure: ?
417 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.05068 (7)0.50195 (8)0.59220 (8)0.0556 (4)
H10.00800.51000.57930.083*
O20.30227 (7)0.59048 (8)0.70861 (10)0.0655 (4)
H20.33610.62070.72740.098*
O30.09894 (7)0.46622 (7)0.47788 (7)0.0427 (3)
N10.17949 (8)0.53425 (8)0.58664 (9)0.0413 (4)
H1A0.20110.57680.60170.050*
C10.09638 (10)0.51566 (10)0.67223 (11)0.0415 (4)
C20.07009 (11)0.53887 (11)0.72002 (13)0.0531 (5)
H2A0.02000.54750.69750.064*
C30.11779 (12)0.54928 (13)0.80092 (14)0.0619 (6)
H30.10000.56480.83320.074*
C40.19150 (13)0.53670 (14)0.83396 (13)0.0659 (6)
H40.22380.54360.88870.079*
C50.21785 (11)0.51384 (12)0.78609 (12)0.0533 (5)
H50.26800.50510.80920.064*
C60.17118 (9)0.50360 (10)0.70431 (11)0.0391 (4)
C70.19871 (9)0.47856 (9)0.65004 (10)0.0376 (4)
H70.17270.43230.62370.045*
C80.28056 (9)0.46165 (10)0.69505 (11)0.0399 (4)
C90.33020 (10)0.52005 (11)0.72284 (12)0.0473 (5)
C100.40660 (11)0.50776 (14)0.76622 (13)0.0600 (6)
H100.43900.54790.78340.072*
C110.43294 (11)0.43680 (15)0.78296 (13)0.0641 (6)
H110.48360.42900.81200.077*
C120.38526 (12)0.37479 (13)0.75730 (12)0.0552 (5)
C130.30753 (10)0.38715 (11)0.71243 (10)0.0431 (4)
C140.26164 (12)0.32330 (11)0.68782 (12)0.0531 (5)
H140.21080.32960.65900.064*
C150.28989 (16)0.25316 (13)0.70521 (14)0.0739 (7)
H150.25840.21230.68760.089*
C160.36600 (18)0.24206 (16)0.74933 (16)0.0850 (9)
H160.38500.19390.76150.102*
C170.41189 (15)0.30083 (17)0.77423 (14)0.0747 (8)
H170.46240.29260.80330.090*
C180.13247 (10)0.52537 (10)0.50919 (11)0.0398 (4)
C190.12036 (14)0.59206 (12)0.45734 (14)0.0709 (7)
H19A0.14260.58350.42610.106*
H19B0.14220.63520.49060.106*
H19C0.06850.60020.42210.106*
O1A−0.04220 (8)0.82226 (9)0.16047 (8)0.0572 (4)
H1A10.00180.81900.17650.086*
O2A0.05897 (8)0.65781 (7)0.02450 (8)0.0532 (4)
H2A10.06880.62240.00510.080*
O3A0.11589 (7)0.79276 (7)0.26185 (8)0.0472 (3)
N1A0.06323 (8)0.72763 (8)0.14574 (8)0.0364 (3)
H1A20.05530.68350.12570.044*
C1A−0.08229 (10)0.80834 (10)0.08044 (12)0.0444 (4)
C2A−0.15812 (11)0.80967 (13)0.03873 (14)0.0591 (6)
H2A2−0.18260.81960.06560.071*
C3A−0.19743 (13)0.79645 (16)−0.04221 (16)0.0768 (8)
H3A−0.24860.7973−0.07000.092*
C4A−0.16199 (13)0.78190 (18)−0.08270 (15)0.0820 (8)
H4A−0.18880.7730−0.13770.098*
C5A−0.08569 (12)0.78056 (14)−0.04061 (12)0.0613 (6)
H5A−0.06170.7708−0.06800.074*
C6A−0.04459 (10)0.79339 (10)0.04089 (11)0.0412 (4)
C7A0.03910 (9)0.79041 (9)0.08923 (10)0.0361 (4)
H7A0.05620.83610.12140.043*
C8A0.07419 (9)0.78832 (9)0.03854 (10)0.0361 (4)
C9A0.08438 (10)0.72246 (10)0.00967 (11)0.0421 (4)
C10A0.11902 (12)0.72005 (12)−0.03502 (12)0.0547 (5)
H10A0.12680.6744−0.05200.066*
C11A0.14087 (12)0.78344 (13)−0.05326 (12)0.0573 (6)
H11A0.16440.7810−0.08210.069*
C12A0.12871 (10)0.85341 (11)−0.02947 (11)0.0471 (5)
C13A0.09502 (9)0.85622 (10)0.01715 (10)0.0385 (4)
C14A0.08239 (10)0.92775 (10)0.03835 (12)0.0478 (5)
H14A0.06050.93150.06890.057*
C15A0.10157 (12)0.99152 (12)0.01502 (14)0.0618 (6)
H15A0.09271.03780.02990.074*
C16A0.13439 (13)0.98752 (14)−0.03111 (15)0.0678 (7)
H16A0.14711.0310−0.04710.081*
C17A0.14749 (12)0.92046 (14)−0.05222 (13)0.0609 (6)
H17A0.16950.9183−0.08260.073*
C18A0.09592 (9)0.73285 (9)0.22438 (10)0.0376 (4)
C19A0.10774 (14)0.66185 (12)0.26910 (13)0.0664 (6)
H19D0.15760.64550.29120.100*
H19E0.07460.62450.23320.100*
H19F0.09860.66980.31180.100*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0317 (7)0.0809 (10)0.0451 (8)0.0032 (6)0.0138 (6)−0.0079 (7)
O20.0455 (8)0.0528 (9)0.0865 (11)−0.0171 (6)0.0263 (8)−0.0101 (8)
O30.0459 (7)0.0437 (7)0.0373 (7)−0.0037 (5)0.0210 (6)0.0021 (5)
N10.0413 (8)0.0384 (8)0.0412 (9)−0.0073 (6)0.0195 (7)0.0029 (6)
C10.0359 (10)0.0454 (10)0.0392 (10)−0.0024 (7)0.0170 (8)−0.0011 (8)
C20.0417 (11)0.0628 (13)0.0575 (13)0.0017 (9)0.0278 (10)−0.0055 (10)
C30.0575 (14)0.0827 (16)0.0557 (14)−0.0054 (11)0.0367 (12)−0.0149 (11)
C40.0558 (14)0.0982 (18)0.0403 (12)−0.0084 (12)0.0226 (11)−0.0121 (11)
C50.0383 (10)0.0776 (14)0.0405 (12)−0.0030 (9)0.0181 (9)−0.0024 (10)
C60.0347 (9)0.0431 (9)0.0384 (10)−0.0037 (7)0.0183 (8)0.0017 (8)
C70.0344 (9)0.0394 (9)0.0353 (10)−0.0045 (7)0.0156 (8)0.0017 (7)
C80.0336 (9)0.0510 (10)0.0345 (10)−0.0024 (7)0.0173 (8)−0.0013 (8)
C90.0376 (10)0.0579 (12)0.0466 (12)−0.0060 (8)0.0221 (9)−0.0049 (9)
C100.0359 (11)0.0898 (17)0.0515 (13)−0.0125 (11)0.0208 (10)−0.0118 (11)
C110.0339 (11)0.108 (2)0.0452 (13)0.0087 (11)0.0170 (9)−0.0039 (12)
C120.0496 (12)0.0800 (15)0.0343 (11)0.0183 (11)0.0207 (9)0.0040 (10)
C130.0440 (10)0.0565 (11)0.0288 (9)0.0069 (8)0.0190 (8)0.0016 (8)
C140.0631 (13)0.0502 (11)0.0416 (11)0.0043 (9)0.0243 (10)0.0037 (9)
C150.103 (2)0.0525 (13)0.0569 (15)0.0120 (12)0.0349 (14)0.0057 (11)
C160.116 (2)0.0699 (17)0.0615 (16)0.0430 (17)0.0412 (17)0.0142 (14)
C170.0735 (16)0.096 (2)0.0478 (14)0.0407 (15)0.0266 (12)0.0112 (13)
C180.0392 (10)0.0421 (10)0.0400 (11)0.0004 (7)0.0220 (8)0.0062 (8)
C190.0904 (17)0.0539 (13)0.0561 (14)−0.0071 (11)0.0296 (13)0.0165 (11)
O1A0.0482 (8)0.0822 (10)0.0491 (9)0.0035 (7)0.0308 (7)−0.0040 (7)
O2A0.0785 (10)0.0377 (7)0.0558 (9)−0.0008 (6)0.0437 (8)−0.0059 (6)
O3A0.0497 (8)0.0510 (8)0.0430 (8)−0.0150 (6)0.0257 (6)−0.0112 (6)
N1A0.0441 (8)0.0343 (7)0.0327 (8)0.0001 (6)0.0212 (7)−0.0004 (6)
C1A0.0443 (11)0.0470 (10)0.0448 (11)0.0062 (8)0.0253 (9)0.0098 (8)
C2A0.0468 (12)0.0752 (15)0.0633 (15)0.0115 (10)0.0343 (11)0.0171 (11)
C3A0.0406 (12)0.117 (2)0.0626 (16)0.0098 (12)0.0201 (12)0.0232 (14)
C4A0.0492 (14)0.140 (3)0.0415 (13)0.0071 (14)0.0133 (11)0.0125 (14)
C5A0.0530 (13)0.0939 (17)0.0376 (12)0.0075 (11)0.0242 (10)0.0092 (11)
C6A0.0427 (10)0.0449 (10)0.0398 (10)0.0053 (7)0.0241 (8)0.0085 (8)
C7A0.0433 (10)0.0335 (8)0.0362 (10)0.0019 (7)0.0241 (8)0.0024 (7)
C8A0.0378 (9)0.0396 (9)0.0314 (9)0.0033 (7)0.0184 (8)0.0018 (7)
C9A0.0482 (11)0.0436 (10)0.0361 (10)0.0038 (8)0.0231 (9)0.0012 (8)
C10A0.0682 (14)0.0587 (13)0.0486 (12)0.0087 (10)0.0384 (11)−0.0051 (10)
C11A0.0640 (14)0.0759 (15)0.0486 (13)0.0025 (11)0.0410 (11)−0.0010 (10)
C12A0.0430 (11)0.0617 (12)0.0361 (10)−0.0028 (8)0.0203 (9)0.0056 (9)
C13A0.0350 (9)0.0464 (10)0.0310 (9)−0.0001 (7)0.0151 (8)0.0038 (7)
C14A0.0511 (11)0.0443 (10)0.0497 (12)0.0021 (8)0.0275 (10)0.0048 (9)
C15A0.0647 (14)0.0450 (11)0.0678 (15)−0.0017 (9)0.0291 (12)0.0083 (10)
C16A0.0716 (15)0.0637 (15)0.0650 (15)−0.0153 (11)0.0335 (13)0.0165 (12)
C17A0.0608 (13)0.0790 (16)0.0479 (13)−0.0136 (11)0.0319 (11)0.0091 (11)
C18A0.0360 (9)0.0429 (10)0.0353 (10)−0.0027 (7)0.0194 (8)−0.0010 (8)
C19A0.0892 (17)0.0554 (13)0.0411 (12)−0.0012 (11)0.0245 (12)0.0092 (10)
Geometric parameters (Å, °) top
O1—C11.365 (2)O1A—H1A10.8200
O1—H10.8200O2A—C9A1.372 (2)
O2—C91.361 (2)O2A—H2A10.8200
O2—H20.8200O3A—C18A1.243 (2)
O3—C181.246 (2)N1A—C18A1.318 (2)
N1—C181.317 (2)N1A—C7A1.469 (2)
N1—C71.473 (2)N1A—H1A20.8600
N1—H1A0.8600C1A—C2A1.378 (3)
C1—C21.379 (3)C1A—C6A1.400 (3)
C1—C61.391 (2)C2A—C3A1.369 (3)
C2—C31.374 (3)C2A—H2A20.9300
C2—H2A0.9300C3A—C4A1.373 (4)
C3—C41.369 (3)C3A—H3A0.9300
C3—H30.9300C4A—C5A1.386 (3)
C4—C51.380 (3)C4A—H4A0.9300
C4—H40.9300C5A—C6A1.378 (3)
C5—C61.384 (3)C5A—H5A0.9300
C5—H50.9300C6A—C7A1.521 (2)
C6—C71.521 (3)C7A—C8A1.520 (2)
C7—C81.518 (2)C7A—H7A0.9800
C7—H70.9800C8A—C9A1.374 (2)
C8—C91.382 (3)C8A—C13A1.430 (2)
C8—C131.423 (3)C9A—C10A1.406 (3)
C9—C101.405 (3)C10A—C11A1.344 (3)
C10—C111.360 (3)C10A—H10A0.9300
C10—H100.9300C11A—C12A1.408 (3)
C11—C121.410 (3)C11A—H11A0.9300
C11—H110.9300C12A—C17A1.410 (3)
C12—C171.412 (3)C12A—C13A1.423 (3)
C12—C131.429 (3)C13A—C14A1.416 (3)
C13—C141.416 (3)C14A—C15A1.370 (3)
C14—C151.358 (3)C14A—H14A0.9300
C14—H140.9300C15A—C16A1.400 (4)
C15—C161.397 (4)C15A—H15A0.9300
C15—H150.9300C16A—C17A1.347 (3)
C16—C171.344 (4)C16A—H16A0.9300
C16—H160.9300C17A—H17A0.9300
C17—H170.9300C18A—O3A1.243 (2)
C18—O31.246 (2)C18A—O3A1.243 (2)
C18—C191.499 (3)C18A—C19A1.489 (3)
C19—H19A0.9600C19A—H19D0.9600
C19—H19B0.9600C19A—H19E0.9600
C19—H19C0.9600C19A—H19F0.9600
O1A—C1A1.357 (2)
C1—O1—H1109.5C9A—O2A—H2A1109.5
C9—O2—H2109.5C18A—N1A—C7A125.89 (14)
C18—N1—C7126.49 (14)C18A—N1A—H1A2117.1
C18—N1—H1A116.8C7A—N1A—H1A2117.1
C7—N1—H1A116.8O1A—C1A—C2A121.13 (18)
O1—C1—C2122.04 (16)O1A—C1A—C6A118.25 (16)
O1—C1—C6116.91 (17)C2A—C1A—C6A120.61 (19)
C2—C1—C6121.03 (17)C3A—C2A—C1A120.1 (2)
C3—C2—C1120.10 (18)C3A—C2A—H2A2119.9
C3—C2—H2A120.0C1A—C2A—H2A2119.9
C1—C2—H2A120.0C2A—C3A—C4A120.6 (2)
C4—C3—C2119.9 (2)C2A—C3A—H3A119.7
C4—C3—H3120.1C4A—C3A—H3A119.7
C2—C3—H3120.1C3A—C4A—C5A119.2 (2)
C3—C4—C5120.1 (2)C3A—C4A—H4A120.4
C3—C4—H4120.0C5A—C4A—H4A120.4
C5—C4—H4120.0C6A—C5A—C4A121.6 (2)
C6—C5—C4121.34 (19)C6A—C5A—H5A119.2
C6—C5—H5119.3C4A—C5A—H5A119.2
C4—C5—H5119.3C5A—C6A—C1A117.88 (17)
C5—C6—C1117.60 (18)C5A—C6A—C7A122.95 (17)
C5—C6—C7122.49 (16)C1A—C6A—C7A119.16 (16)
C1—C6—C7119.90 (16)N1A—C7A—C8A111.85 (13)
N1—C7—C8110.73 (14)N1A—C7A—C6A109.32 (13)
N1—C7—C6110.26 (14)C8A—C7A—C6A114.26 (14)
C8—C7—C6113.48 (14)N1A—C7A—H7A107.0
N1—C7—H7107.4C8A—C7A—H7A107.0
C8—C7—H7107.4C6A—C7A—H7A107.0
C6—C7—H7107.4C9A—C8A—C13A118.19 (16)
C9—C8—C13119.13 (17)C9A—C8A—C7A121.65 (15)
C9—C8—C7119.21 (16)C13A—C8A—C7A120.11 (15)
C13—C8—C7121.61 (15)O2A—C9A—C8A118.40 (16)
O2—C9—C8117.37 (16)O2A—C9A—C10A119.78 (16)
O2—C9—C10120.90 (18)C8A—C9A—C10A121.81 (17)
C8—C9—C10121.71 (19)C11A—C10A—C9A120.26 (18)
C11—C10—C9119.6 (2)C11A—C10A—H10A119.9
C11—C10—H10120.2C9A—C10A—H10A119.9
C9—C10—H10120.2C10A—C11A—C12A121.17 (19)
C10—C11—C12121.49 (19)C10A—C11A—H11A119.4
C10—C11—H11119.3C12A—C11A—H11A119.4
C12—C11—H11119.3C11A—C12A—C17A121.7 (2)
C11—C12—C17122.1 (2)C11A—C12A—C13A118.89 (17)
C11—C12—C13118.98 (19)C17A—C12A—C13A119.44 (19)
C17—C12—C13119.0 (2)C14A—C13A—C12A117.06 (16)
C14—C13—C8123.81 (17)C14A—C13A—C8A123.40 (17)
C14—C13—C12117.12 (18)C12A—C13A—C8A119.53 (16)
C8—C13—C12119.06 (18)C15A—C14A—C13A121.6 (2)
C15—C14—C13121.8 (2)C15A—C14A—H14A119.2
C15—C14—H14119.1C13A—C14A—H14A119.2
C13—C14—H14119.1C14A—C15A—C16A120.4 (2)
C14—C15—C16120.4 (3)C14A—C15A—H15A119.8
C14—C15—H15119.8C16A—C15A—H15A119.8
C16—C15—H15119.8C17A—C16A—C15A119.7 (2)
C17—C16—C15120.1 (2)C17A—C16A—H16A120.2
C17—C16—H16119.9C15A—C16A—H16A120.2
C15—C16—H16119.9C16A—C17A—C12A121.8 (2)
C16—C17—C12121.6 (2)C16A—C17A—H17A119.1
C16—C17—H17119.2C12A—C17A—H17A119.1
C12—C17—H17119.2O3A—C18A—N1A123.91 (16)
O3—C18—N1124.33 (16)O3A—C18A—N1A123.91 (16)
O3—C18—N1124.33 (16)O3A—C18A—N1A123.91 (16)
O3—C18—C19119.64 (17)O3A—C18A—C19A119.49 (17)
O3—C18—C19119.64 (17)O3A—C18A—C19A119.49 (17)
N1—C18—C19116.02 (17)O3A—C18A—C19A119.49 (17)
C18—C19—H19A109.5N1A—C18A—C19A116.59 (16)
C18—C19—H19B109.5C18A—C19A—H19D109.5
H19A—C19—H19B109.5C18A—C19A—H19E109.5
C18—C19—H19C109.5H19D—C19A—H19E109.5
H19A—C19—H19C109.5C18A—C19A—H19F109.5
H19B—C19—H19C109.5H19D—C19A—H19F109.5
C1A—O1A—H1A1109.5H19E—C19A—H19F109.5
O1—C1—C2—C3177.50 (19)C6A—C1A—C2A—C3A−0.1 (3)
C6—C1—C2—C3−1.1 (3)C1A—C2A—C3A—C4A−0.1 (4)
C1—C2—C3—C40.1 (3)C2A—C3A—C4A—C5A0.1 (4)
C2—C3—C4—C50.2 (4)C3A—C4A—C5A—C6A0.1 (4)
C3—C4—C5—C60.4 (4)C4A—C5A—C6A—C1A−0.3 (3)
C4—C5—C6—C1−1.3 (3)C4A—C5A—C6A—C7A178.4 (2)
C4—C5—C6—C7179.9 (2)O1A—C1A—C6A—C5A−178.92 (18)
O1—C1—C6—C5−177.01 (17)C2A—C1A—C6A—C5A0.3 (3)
C2—C1—C6—C51.7 (3)O1A—C1A—C6A—C7A2.3 (2)
O1—C1—C6—C71.8 (2)C2A—C1A—C6A—C7A−178.44 (17)
C2—C1—C6—C7−179.54 (17)C18A—N1A—C7A—C8A122.33 (17)
C18—N1—C7—C8120.86 (18)C18A—N1A—C7A—C6A−110.10 (18)
C18—N1—C7—C6−112.71 (19)C5A—C6A—C7A—N1A−114.0 (2)
C5—C6—C7—N1−121.32 (19)C1A—C6A—C7A—N1A64.7 (2)
C1—C6—C7—N159.9 (2)C5A—C6A—C7A—C8A12.2 (2)
C5—C6—C7—C83.5 (2)C1A—C6A—C7A—C8A−169.11 (15)
C1—C6—C7—C8−175.20 (15)N1A—C7A—C8A—C9A39.0 (2)
N1—C7—C8—C949.0 (2)C6A—C7A—C8A—C9A−85.9 (2)
C6—C7—C8—C9−75.7 (2)N1A—C7A—C8A—C13A−143.40 (15)
N1—C7—C8—C13−133.86 (17)C6A—C7A—C8A—C13A91.73 (19)
C6—C7—C8—C13101.53 (19)C13A—C8A—C9A—O2A−174.72 (15)
C13—C8—C9—O2−176.66 (17)C7A—C8A—C9A—O2A2.9 (3)
C7—C8—C9—O20.6 (3)C13A—C8A—C9A—C10A4.5 (3)
C13—C8—C9—C101.5 (3)C7A—C8A—C9A—C10A−177.87 (17)
C7—C8—C9—C10178.75 (18)O2A—C9A—C10A—C11A176.72 (19)
O2—C9—C10—C11176.8 (2)C8A—C9A—C10A—C11A−2.5 (3)
C8—C9—C10—C11−1.3 (3)C9A—C10A—C11A—C12A−1.0 (3)
C9—C10—C11—C120.4 (3)C10A—C11A—C12A—C17A−176.2 (2)
C10—C11—C12—C17179.9 (2)C10A—C11A—C12A—C13A2.3 (3)
C10—C11—C12—C130.2 (3)C11A—C12A—C13A—C14A−178.70 (18)
C9—C8—C13—C14179.16 (18)C17A—C12A—C13A—C14A−0.2 (3)
C7—C8—C13—C142.0 (3)C11A—C12A—C13A—C8A−0.2 (3)
C9—C8—C13—C12−0.8 (3)C17A—C12A—C13A—C8A178.39 (17)
C7—C8—C13—C12−177.97 (17)C9A—C8A—C13A—C14A175.33 (17)
C11—C12—C13—C14179.99 (19)C7A—C8A—C13A—C14A−2.4 (3)
C17—C12—C13—C140.3 (3)C9A—C8A—C13A—C12A−3.1 (2)
C11—C12—C13—C8−0.1 (3)C7A—C8A—C13A—C12A179.18 (15)
C17—C12—C13—C8−179.79 (19)C12A—C13A—C14A—C15A0.1 (3)
C8—C13—C14—C15179.4 (2)C8A—C13A—C14A—C15A−178.39 (18)
C12—C13—C14—C15−0.7 (3)C13A—C14A—C15A—C16A0.2 (3)
C13—C14—C15—C160.9 (4)C14A—C15A—C16A—C17A−0.4 (3)
C14—C15—C16—C17−0.7 (4)C15A—C16A—C17A—C12A0.3 (4)
C15—C16—C17—C120.3 (4)C11A—C12A—C17A—C16A178.5 (2)
C11—C12—C17—C16−179.8 (2)C13A—C12A—C17A—C16A−0.1 (3)
C13—C12—C17—C16−0.1 (4)C7A—N1A—C18A—O3A−5.8 (3)
C7—N1—C18—O3−2.7 (3)C7A—N1A—C18A—O3A−5.8 (3)
C7—N1—C18—O3−2.7 (3)C7A—N1A—C18A—O3A−5.8 (3)
C7—N1—C18—C19177.57 (19)C7A—N1A—C18A—C19A173.15 (18)
O1A—C1A—C2A—C3A179.1 (2)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O3i0.821.992.792 (2)166
O2A—H2A1···O3ii0.821.892.702 (2)170
O2—H2···O3Aiii0.821.812.588 (2)159
O1A—H1A1···O3A0.822.162.928 (2)156
C7—H7···O30.982.512.901 (2)104
C7A—H7A···O3A0.982.472.879 (2)105
Symmetry codes: (i) −x, −y+1, −z+1; (ii) x, −y+1, z−1/2; (iii) −x+1/2, −y+3/2, −z+1.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O3i0.821.992.792 (2)166
O2A—H2A1···O3ii0.821.892.702 (2)170
O2—H2···O3Aiii0.821.812.588 (2)159
O1A—H1A1···O3A0.822.162.928 (2)156
C7—H7···O30.982.512.901 (2)104
C7A—H7A···O3A0.982.472.879 (2)105
Symmetry codes: (i) −x, −y+1, −z+1; (ii) x, −y+1, z−1/2; (iii) −x+1/2, −y+3/2, −z+1.
Acknowledgements top

The authors thank Dr Babu Vargheese, SAIF, IIT, Madras, India, for his help in collecting the X-ray intensity data. MNM and ASP thank Dr J. Jothi Kumar, Principal of Presidency College, Chennai, India, for providing computer and internet facilities.

references
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