PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2010 November 1; 66(Pt 11): o2781.
Published online 2010 October 9. doi:  10.1107/S1600536810039656
PMCID: PMC3009366

N-[4-(Phenyl­imino­meth­yl)phen­yl]acetamide 0.67-hydrate

Abstract

The title compound, C15H14N2O·0.67H2O, was prepared by the reaction of 4-acetoamine­benzaldehyde and aniline. The asymmetric unit contains six organic mol­ecules and four water mol­ecules. The dihedral angles between the aromatic ring planes in each organic mol­ecule vary from 42.4 (2) to 53.8 (2)°. In the crystal, an extensive network of inter­molecular N—H(...)O, O—H(...)N and O—H(...)O hydrogen bonds link the mol­ecules into [010] chains.

Related literature

For background to polydentate Schiff bases in coordination chemistry, see: Souza et al. (1985 [triangle]); Dixit et al. (2009 [triangle]). For information on their uses as stereospecific catalysts, see: Kureshy et al. (1999 [triangle]); Aoyama et al. (1986 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o2781-scheme1.jpg

Experimental

Crystal data

  • C15H14N2O·0.67H2O
  • M r = 250.29
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2781-efi1.jpg
  • a = 21.328 (4) Å
  • b = 17.797 (3) Å
  • c = 23.021 (4) Å
  • β = 117.244 (4)°
  • V = 7769 (3) Å3
  • Z = 24
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 100 K
  • 0.60 × 0.35 × 0.10 mm

Data collection

  • Bruker SMART CCD diffractometer
  • 40121 measured reflections
  • 13696 independent reflections
  • 4483 reflections with I > 2σ(I)
  • R int = 0.113

Refinement

  • R[F 2 > 2σ(F 2)] = 0.055
  • wR(F 2) = 0.119
  • S = 0.76
  • 13696 reflections
  • 1057 parameters
  • 23 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.34 e Å−3
  • Δρmin = −0.21 e Å−3

Data collection: SMART (Bruker, 2001 [triangle]); cell refinement: SAINT (Bruker, 2002 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]) and PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: SHELXTL and PLATON.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810039656/hb5642sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810039656/hb5642Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors thank the University of the Punjab and the Higher Education Commission (HEC), Government of Pakistan, for financial support, and are also grateful to the School of Chemistry, The University of Manchester, England, for providing research facilities.

supplementary crystallographic information

Comment

Polydentate Schiff base ligands are widely used in the preparation of transition metal complexes (Souza et al., 1985). Some such complexes possess binding sites and cavities for various cations, anions and organic molecules (Dixit et al., 2009). In addition, Schiff base metal complexes can be effective as stereospecific catalysts for oxidation (Kureshy et al., 1999), reduction (Aoyama et al., 1986) and other transformations in organic and inorganic chemistry. The title Schiff base compound was synthesized from 4-acetoaminebenzaldehyde and aniline as a potential ligand for the preparation of transition metal complexes.

The asymmetric unit contains six molecules of 4-acetylaminobenzylidine aniline (I) and four water molecules. Figure 1 shows a plot of one of the molecules of (I). The dihedral angles between the two aromatic ring planes in each molecule of (I) vary from 42.4 (2) to 53.8 (2)° (Table 2). The six molecules in the asymetric unit are arranged in pairs, one above the other. There are possible π-stacking interactions between the carbonyl group of each molecule in the pair with the central phenyl group of the molecule above or below it, with carbonyl O and C atoms to aromatic ring distances varying from 3.002 (4) to 3.421 (4) Å and 3.191 (6) to 3.492 (6) Å, respectively (Table 3, Figure 2). The paired molecules are further linked to one another by O—H···N and O—H···O hydrogen bonds from two water molecules, one at each side of the pair (Table 1, Figure 2). Each pair of molecules is linked to adjacent pairs on either side by N—H···O contacts (Table 3), either to water O atoms (i.e. the N1—H1···O1S, N3—H3···O2S, N5—H5···O4S and N7—H7···O3S contacts) or to a carbonyl oxygen of the next molecule (i.e. the N11—H11···O2 and the N9—H9···O4 contacts). In this way, the pairs of molecules are linked into chains along b, as shown in Figure 2.

Experimental

0.0163 g (1.0 mmol) of 4-acetoaminebenzaldehyde and 0.0911 ml (1.0 mmol) of aniline were dissolved in 10.0 ml 95% ethanol separately. Both solutions were mixed in 100 ml round bottom flask. The mixture was refluxed for two hours at 423 K. It was then recrystallized by using a mixture of acetonitrile, methanol and water in the ratio 1: 3: 4 respectively.

Refinement

H atoms bonded to C were included in calculated positions using the riding method, with aromatic and methyl C—H distances of 0.98 and 0.95 Å, respectively and Ueq values 1.2 and 1.5 times those of the parent atoms; the torsion angles of the methyl H atoms were optimized to give the best fit to the electron density. H atoms bonded to N and O were found by difference Fourier methods and refined isotropically with restraints on the bond lengths and with the Ueq value constrained to be 1.2 or 1.5 times that of the parent atom. The N—H distances vary from 0.86 (2) to 0.88 (2) Å and the O—H distances range from 0.83 (2) to 0.98 (2) Å.

Figures

Fig. 1.
Plot of one molecule of (I) with ellipsoids drawn at the 50% probability level.
Fig. 2.
Plot showing the packing arrangement of the crystal structure of (I) viewed down a showing pairs of molecules linked to each other by hydrogen bonding interactions, to form a chain along b. Only H atoms involved in hydrogen bonding are shown. Symmetry ...

Crystal data

C15H14N2O·0.67H2OF(000) = 3184
Mr = 250.29Dx = 1.284 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 766 reflections
a = 21.328 (4) Åθ = 2.9–24.5°
b = 17.797 (3) ŵ = 0.09 mm1
c = 23.021 (4) ÅT = 100 K
β = 117.244 (4)°Plate, colourless
V = 7769 (3) Å30.60 × 0.35 × 0.10 mm
Z = 24

Data collection

Bruker SMART CCD diffractometer4483 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.113
graphiteθmax = 25.0°, θmin = 2.1°
phi and ω scansh = −25→24
40121 measured reflectionsk = −20→21
13696 independent reflectionsl = −27→26

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119H atoms treated by a mixture of independent and constrained refinement
S = 0.76w = 1/[σ2(Fo2) + (0.0147P)2] where P = (Fo2 + 2Fc2)/3
13696 reflections(Δ/σ)max = 0.001
1057 parametersΔρmax = 0.34 e Å3
23 restraintsΔρmin = −0.21 e Å3

Special details

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

xyzUiso*/Ueq
O10.18362 (17)0.05033 (18)0.33952 (15)0.0264 (9)
N10.1999 (2)0.1750 (2)0.3278 (2)0.0174 (10)
H1N0.2190 (19)0.2159 (14)0.3501 (16)0.021*
N20.1041 (2)0.2783 (2)0.03041 (18)0.0190 (11)
C10.2263 (2)0.1271 (2)0.43504 (19)0.0220 (12)
H1A0.18540.13530.44290.033*
H1B0.25680.17160.44890.033*
H1C0.25280.08330.46000.033*
C20.2016 (2)0.1134 (3)0.3628 (2)0.0169 (12)
C30.1748 (2)0.1801 (3)0.2598 (2)0.0175 (12)
C40.1439 (2)0.1227 (3)0.2154 (2)0.0221 (13)
H40.13890.07420.23010.027*
C50.1203 (2)0.1357 (3)0.1500 (2)0.0239 (13)
H50.09950.09550.12010.029*
C60.1259 (2)0.2050 (3)0.1263 (2)0.0151 (12)
C70.1558 (2)0.2640 (3)0.1704 (2)0.0212 (13)
H70.16020.31240.15520.025*
C80.1792 (2)0.2516 (3)0.2364 (2)0.0201 (12)
H80.19850.29210.26620.024*
C90.1008 (3)0.2157 (3)0.0562 (2)0.0221 (13)
H90.08090.17380.02820.027*
C100.0809 (3)0.2823 (3)−0.0384 (2)0.0203 (13)
C110.0973 (2)0.2264 (3)−0.0729 (2)0.0203 (12)
H110.12190.1822−0.05120.024*
C120.0771 (2)0.2368 (3)−0.1387 (2)0.0235 (13)
H120.08810.1994−0.16210.028*
C130.0411 (3)0.3008 (3)−0.1708 (2)0.0245 (14)
H130.02800.3075−0.21590.029*
C140.0244 (3)0.3552 (3)−0.1371 (2)0.0244 (14)
H14−0.00100.3988−0.15930.029*
C150.0447 (3)0.3462 (3)−0.0713 (2)0.0213 (13)
H150.03380.3841−0.04830.026*
O20.31874 (18)0.63435 (18)0.16385 (15)0.0252 (9)
N30.2971 (2)0.5096 (2)0.16793 (19)0.0168 (10)
H3N0.2778 (19)0.4694 (15)0.1456 (17)0.020*
N40.3898 (2)0.3942 (2)0.46400 (18)0.0209 (11)
C160.2677 (2)0.5655 (3)0.0640 (2)0.0287 (13)
H16A0.23270.60480.04150.043*
H16B0.24540.51610.05080.043*
H16C0.30630.56970.05220.043*
C170.2961 (2)0.5746 (3)0.1357 (2)0.0203 (12)
C180.3253 (2)0.4967 (3)0.2350 (2)0.0182 (12)
C190.3067 (2)0.4306 (3)0.2562 (2)0.0196 (12)
H190.27640.39540.22490.024*
C200.3318 (2)0.4156 (3)0.3219 (2)0.0183 (12)
H200.31910.36990.33510.022*
C210.3753 (2)0.4664 (3)0.3694 (2)0.0192 (13)
C220.3943 (2)0.5310 (3)0.3481 (2)0.0209 (13)
H220.42470.56580.37980.025*
C230.3710 (2)0.5473 (3)0.2821 (2)0.0203 (12)
H230.38570.59200.26930.024*
C240.4008 (2)0.4543 (3)0.4389 (2)0.0210 (13)
H240.42740.49330.46780.025*
C250.4151 (3)0.3917 (3)0.5331 (2)0.0202 (13)
C260.4487 (3)0.3259 (3)0.5653 (2)0.0233 (13)
H260.45670.28620.54190.028*
C270.4705 (3)0.3189 (3)0.6320 (3)0.0276 (14)
H270.49390.27450.65420.033*
C280.4581 (2)0.3768 (3)0.6666 (2)0.0268 (14)
H280.47280.37160.71210.032*
C290.4245 (2)0.4418 (3)0.6343 (2)0.0273 (14)
H290.41630.48120.65790.033*
C300.4025 (2)0.4500 (3)0.5670 (2)0.0241 (13)
H300.37920.49450.54490.029*
O30.32175 (18)0.27632 (18)0.16364 (15)0.0270 (9)
N50.3035 (2)0.1528 (2)0.1761 (2)0.0240 (11)
H5N0.293 (2)0.1107 (14)0.1558 (18)0.029*
N60.3977 (2)0.0503 (2)0.47430 (19)0.0223 (11)
C310.2754 (2)0.1980 (2)0.0682 (2)0.0255 (13)
H31A0.24080.23640.04280.038*
H31B0.25310.14830.05750.038*
H31C0.31490.19930.05740.038*
C320.3021 (3)0.2130 (3)0.1394 (2)0.0251 (13)
C330.3298 (2)0.1451 (3)0.2438 (2)0.0178 (12)
C340.3252 (2)0.0740 (3)0.2680 (2)0.0241 (13)
H340.30650.03270.23880.029*
C350.3475 (2)0.0640 (3)0.3333 (2)0.0204 (13)
H350.34420.01540.34870.025*
C360.3749 (2)0.1224 (3)0.3781 (2)0.0182 (12)
C370.3796 (2)0.1938 (3)0.3543 (2)0.0227 (13)
H370.39820.23480.38370.027*
C380.3571 (2)0.2049 (3)0.2877 (2)0.0229 (13)
H380.36040.25340.27210.028*
C390.3986 (2)0.1140 (3)0.4476 (2)0.0220 (13)
H390.41540.15710.47480.026*
C400.4198 (2)0.0468 (3)0.5425 (2)0.0184 (12)
C410.4593 (2)−0.0158 (3)0.5761 (2)0.0224 (13)
H410.4716−0.05270.55320.027*
C420.4807 (3)−0.0249 (3)0.6421 (2)0.0233 (13)
H420.5087−0.06710.66450.028*
C430.4617 (2)0.0272 (3)0.6757 (2)0.0244 (13)
H430.47530.02050.72080.029*
C440.4223 (2)0.0896 (3)0.6427 (2)0.0237 (13)
H440.40970.12610.66560.028*
C450.4015 (2)0.0987 (3)0.5769 (2)0.0225 (12)
H450.37410.14140.55480.027*
O40.17838 (17)0.69595 (16)0.33253 (15)0.0282 (8)
N70.2032 (2)0.8216 (2)0.3298 (2)0.0213 (11)
H7N0.216 (2)0.8614 (16)0.3537 (17)0.026*
N80.1046 (2)0.9396 (2)0.03385 (18)0.0231 (10)
C460.2345 (2)0.7620 (2)0.43357 (19)0.0301 (13)
H46A0.19690.76420.44680.045*
H46B0.26380.80730.44880.045*
H46C0.26380.71750.45290.045*
C470.2022 (2)0.7574 (3)0.3598 (2)0.0212 (12)
C480.1736 (2)0.8347 (2)0.2619 (2)0.0154 (11)
C490.1905 (2)0.9016 (2)0.2411 (2)0.0194 (11)
H490.22060.93640.27290.023*
C500.1653 (2)0.9189 (3)0.1764 (2)0.0211 (12)
H500.17790.96500.16370.025*
C510.1202 (2)0.8678 (3)0.1287 (2)0.0211 (13)
C520.1005 (3)0.8029 (3)0.1492 (2)0.0235 (13)
H520.06850.76920.11750.028*
C530.1264 (2)0.7862 (3)0.2149 (2)0.0241 (13)
H530.11190.74150.22780.029*
C540.0920 (3)0.8812 (3)0.0589 (2)0.0255 (13)
H540.06200.84390.03000.031*
C550.0762 (3)0.9445 (3)−0.0355 (2)0.0214 (13)
C560.0460 (2)1.0108 (3)−0.0670 (2)0.0284 (14)
H560.04331.0518−0.04190.034*
C570.0195 (3)1.0197 (3)−0.1337 (2)0.0290 (14)
H57−0.00211.0656−0.15400.035*
C580.0249 (2)0.9607 (3)−0.1710 (2)0.0277 (13)
H580.00770.9661−0.21680.033*
C590.0555 (2)0.8945 (3)−0.1400 (2)0.0279 (14)
H590.06000.8544−0.16510.034*
C600.0800 (2)0.8846 (3)−0.0738 (2)0.0235 (12)
H600.09930.8376−0.05400.028*
O50.17220 (17)0.41264 (18)0.32528 (15)0.0268 (9)
N90.1768 (2)0.5360 (2)0.30192 (19)0.0212 (10)
H9N0.186 (2)0.5795 (13)0.3216 (17)0.025*
N100.0890 (2)0.6160 (2)0.0028 (2)0.0278 (11)
C610.2153 (2)0.4991 (2)0.4143 (2)0.0312 (14)
H61A0.18660.47630.43290.047*
H61B0.21440.55390.41810.047*
H61C0.26390.48110.43820.047*
C620.1860 (3)0.4777 (3)0.3438 (2)0.0225 (13)
C630.1546 (2)0.5338 (3)0.2337 (2)0.0234 (13)
C640.1207 (2)0.4740 (3)0.1929 (2)0.0242 (13)
H640.11150.42910.21000.029*
C650.1004 (2)0.4807 (3)0.1266 (2)0.0255 (13)
H650.07810.43910.09890.031*
C660.1113 (2)0.5452 (3)0.0990 (2)0.0219 (13)
C670.1455 (2)0.6046 (3)0.1412 (2)0.0248 (13)
H670.15410.64970.12400.030*
C680.1668 (2)0.5993 (3)0.2069 (2)0.0206 (13)
H680.19020.64060.23460.025*
C690.0883 (2)0.5532 (3)0.0296 (2)0.0252 (13)
H690.07200.50980.00270.030*
C700.0689 (3)0.6184 (3)−0.0650 (2)0.0228 (13)
C710.0906 (2)0.5658 (3)−0.0972 (2)0.0278 (13)
H710.11850.5240−0.07390.033*
C720.0718 (3)0.5742 (3)−0.1622 (2)0.0303 (13)
H720.08730.5386−0.18360.036*
C730.0302 (3)0.6346 (3)−0.1970 (2)0.0300 (14)
H730.01660.6400−0.24220.036*
C740.0087 (3)0.6869 (3)−0.1652 (2)0.0321 (14)
H74−0.02010.7280−0.18880.039*
C750.0287 (3)0.6797 (3)−0.0999 (2)0.0250 (14)
H750.01510.7167−0.07820.030*
O60.32500 (17)0.91894 (19)0.17329 (16)0.0318 (9)
N110.3190 (2)0.7942 (2)0.1974 (2)0.0313 (11)
H11N0.303 (2)0.7515 (15)0.1780 (19)0.038*
N120.4177 (2)0.7185 (2)0.4983 (2)0.0247 (11)
C760.2809 (2)0.8298 (2)0.0847 (2)0.0339 (13)
H76A0.31950.82700.07290.051*
H76B0.24630.86720.05730.051*
H76C0.25800.78060.07810.051*
C770.3103 (3)0.8524 (3)0.1566 (2)0.0237 (13)
C780.3446 (2)0.7961 (3)0.2651 (2)0.0218 (12)
C790.3814 (2)0.8570 (3)0.3046 (2)0.0268 (14)
H790.39050.90100.28620.032*
C800.4041 (3)0.8512 (3)0.3707 (2)0.0250 (13)
H800.42770.89280.39770.030*
C810.3938 (2)0.7863 (3)0.4002 (2)0.0227 (13)
C820.3566 (2)0.7262 (3)0.3592 (2)0.0260 (13)
H820.34820.68180.37740.031*
C830.3323 (2)0.7318 (3)0.2930 (2)0.0272 (13)
H830.30670.69120.26570.033*
C840.4202 (2)0.7804 (3)0.4706 (2)0.0277 (14)
H840.43990.82360.49690.033*
C850.4417 (3)0.7169 (3)0.5663 (2)0.0263 (13)
C860.4285 (2)0.7739 (3)0.6005 (2)0.0284 (14)
H860.40420.81790.57800.034*
C870.4501 (2)0.7675 (3)0.6665 (2)0.0311 (14)
H870.44030.80670.68920.037*
C880.4860 (3)0.7042 (3)0.7001 (2)0.0324 (14)
H880.50160.70030.74580.039*
C890.4991 (3)0.6464 (3)0.6666 (2)0.0321 (14)
H890.52380.60280.68940.039*
C900.4764 (3)0.6522 (3)0.6004 (2)0.0287 (14)
H900.48430.61170.57760.034*
O1S0.25984 (18)0.30429 (19)0.40922 (16)0.0264 (9)
H1O0.3019 (11)0.307 (2)0.417 (2)0.040*
H2O0.2331 (19)0.3415 (17)0.3852 (18)0.040*
O2S0.22697 (18)0.38491 (18)0.08542 (16)0.0281 (9)
H3O0.1920 (16)0.356 (2)0.0685 (18)0.042*
H4O0.2586 (19)0.351 (2)0.102 (2)0.042*
O3S0.27737 (17)0.94103 (17)0.41746 (15)0.0292 (8)
H5O0.3144 (15)0.958 (2)0.417 (2)0.044*
H6O0.2460 (18)0.9762 (19)0.3956 (19)0.044*
O4S0.23815 (18)0.02510 (18)0.08989 (16)0.0360 (9)
H7O0.2016 (16)−0.004 (2)0.0729 (19)0.054*
H8O0.2736 (18)−0.010 (2)0.1188 (18)0.054*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.030 (2)0.021 (2)0.024 (2)−0.0057 (17)0.0088 (16)0.0027 (17)
N10.018 (2)0.010 (2)0.023 (3)−0.0049 (19)0.0082 (19)−0.0028 (19)
N20.015 (2)0.027 (3)0.016 (3)−0.007 (2)0.0076 (19)−0.010 (2)
C10.024 (3)0.024 (3)0.017 (3)−0.002 (2)0.008 (2)−0.003 (2)
C20.010 (3)0.016 (3)0.025 (3)0.001 (2)0.008 (2)−0.002 (2)
C30.016 (3)0.022 (3)0.015 (3)0.007 (2)0.007 (2)0.003 (2)
C40.021 (3)0.016 (3)0.027 (3)−0.003 (2)0.009 (2)0.002 (2)
C50.024 (3)0.027 (3)0.016 (3)−0.007 (2)0.006 (2)−0.007 (2)
C60.013 (3)0.016 (3)0.012 (3)0.001 (2)0.002 (2)−0.002 (2)
C70.024 (3)0.021 (3)0.022 (3)−0.001 (2)0.012 (2)0.001 (2)
C80.017 (3)0.017 (3)0.024 (3)−0.003 (2)0.008 (2)−0.008 (2)
C90.016 (3)0.021 (3)0.029 (3)−0.003 (3)0.011 (3)−0.007 (3)
C100.016 (3)0.024 (3)0.024 (3)−0.007 (2)0.012 (2)−0.003 (3)
C110.013 (3)0.024 (3)0.023 (3)0.002 (2)0.006 (2)0.001 (2)
C120.020 (3)0.031 (3)0.017 (3)−0.006 (2)0.007 (2)−0.009 (2)
C130.024 (3)0.036 (4)0.013 (3)−0.004 (3)0.008 (2)−0.002 (3)
C140.022 (3)0.024 (3)0.023 (3)−0.002 (3)0.005 (2)0.007 (3)
C150.018 (3)0.025 (3)0.021 (3)−0.002 (3)0.009 (2)−0.006 (3)
O20.033 (2)0.018 (2)0.025 (2)−0.0072 (17)0.0134 (16)−0.0051 (17)
N30.021 (3)0.013 (2)0.011 (2)−0.0001 (19)0.0037 (19)−0.0033 (19)
N40.022 (3)0.022 (3)0.018 (3)0.003 (2)0.009 (2)0.006 (2)
C160.029 (3)0.028 (3)0.031 (3)−0.001 (2)0.016 (3)0.004 (3)
C170.018 (3)0.024 (3)0.021 (3)0.001 (2)0.011 (2)0.006 (3)
C180.018 (3)0.020 (3)0.023 (3)−0.004 (2)0.014 (2)−0.006 (2)
C190.015 (3)0.024 (3)0.018 (3)−0.004 (2)0.006 (2)−0.005 (2)
C200.024 (3)0.008 (3)0.027 (3)−0.002 (2)0.016 (2)−0.003 (2)
C210.015 (3)0.019 (3)0.027 (3)0.002 (2)0.012 (2)0.004 (3)
C220.021 (3)0.014 (3)0.019 (3)−0.002 (2)0.002 (2)−0.004 (2)
C230.024 (3)0.016 (3)0.020 (3)−0.001 (2)0.010 (2)0.001 (2)
C240.012 (3)0.026 (3)0.023 (3)−0.002 (2)0.007 (2)−0.007 (3)
C250.015 (3)0.021 (3)0.021 (3)−0.006 (2)0.006 (2)0.000 (3)
C260.024 (3)0.023 (3)0.024 (3)−0.007 (3)0.011 (2)−0.003 (3)
C270.021 (3)0.027 (3)0.034 (4)−0.003 (3)0.011 (3)0.006 (3)
C280.017 (3)0.043 (4)0.017 (3)−0.002 (3)0.005 (2)0.006 (3)
C290.023 (3)0.032 (3)0.025 (3)−0.004 (2)0.010 (2)−0.007 (3)
C300.023 (3)0.024 (3)0.022 (3)−0.006 (2)0.008 (2)−0.004 (2)
O30.031 (2)0.019 (2)0.027 (2)−0.0077 (17)0.0102 (16)−0.0071 (17)
N50.028 (3)0.021 (3)0.025 (3)0.000 (2)0.013 (2)−0.006 (2)
N60.021 (2)0.019 (3)0.027 (3)0.0032 (19)0.0101 (19)0.003 (2)
C310.021 (3)0.029 (3)0.029 (3)−0.005 (2)0.013 (2)−0.001 (2)
C320.018 (3)0.032 (4)0.029 (3)0.000 (3)0.013 (2)0.002 (3)
C330.015 (3)0.016 (3)0.025 (3)−0.003 (2)0.010 (2)−0.006 (2)
C340.026 (3)0.024 (3)0.023 (3)0.000 (2)0.011 (2)0.002 (2)
C350.020 (3)0.014 (3)0.031 (3)0.001 (2)0.015 (2)−0.003 (3)
C360.015 (3)0.022 (3)0.021 (3)0.000 (2)0.011 (2)0.004 (2)
C370.016 (3)0.020 (3)0.032 (3)−0.001 (2)0.011 (2)−0.005 (2)
C380.025 (3)0.016 (3)0.034 (3)0.001 (2)0.019 (3)−0.001 (2)
C390.016 (3)0.018 (3)0.033 (3)−0.001 (2)0.012 (2)−0.006 (3)
C400.012 (3)0.019 (3)0.020 (3)−0.002 (2)0.004 (2)0.004 (2)
C410.021 (3)0.020 (3)0.028 (3)−0.006 (2)0.013 (2)−0.004 (2)
C420.021 (3)0.023 (3)0.031 (3)0.004 (2)0.016 (3)0.001 (3)
C430.017 (3)0.032 (3)0.022 (3)−0.002 (3)0.007 (2)0.000 (3)
C440.017 (3)0.029 (3)0.026 (3)−0.004 (2)0.011 (2)−0.013 (3)
C450.021 (3)0.017 (3)0.029 (3)−0.004 (2)0.011 (2)−0.002 (2)
O40.037 (2)0.0192 (19)0.029 (2)−0.0047 (17)0.0163 (17)−0.0014 (17)
N70.023 (3)0.017 (3)0.024 (3)−0.006 (2)0.011 (2)−0.005 (2)
N80.021 (2)0.025 (3)0.021 (3)−0.001 (2)0.0082 (19)−0.001 (2)
C460.029 (3)0.034 (3)0.025 (3)−0.006 (3)0.011 (2)0.001 (3)
C470.022 (3)0.018 (3)0.031 (3)−0.006 (2)0.018 (2)−0.010 (3)
C480.014 (3)0.013 (3)0.018 (3)0.004 (2)0.006 (2)0.002 (2)
C490.028 (3)0.012 (3)0.019 (3)−0.004 (2)0.011 (2)−0.004 (2)
C500.017 (3)0.021 (3)0.025 (3)−0.007 (2)0.009 (2)−0.005 (2)
C510.020 (3)0.028 (3)0.015 (3)0.003 (2)0.008 (2)−0.003 (2)
C520.017 (3)0.026 (3)0.025 (3)−0.003 (2)0.008 (2)−0.004 (3)
C530.018 (3)0.025 (3)0.026 (3)−0.008 (2)0.006 (2)−0.006 (2)
C540.017 (3)0.019 (3)0.039 (4)−0.004 (2)0.012 (3)−0.010 (3)
C550.019 (3)0.020 (3)0.025 (3)−0.004 (2)0.010 (2)−0.005 (3)
C560.023 (3)0.032 (3)0.036 (4)0.005 (3)0.019 (3)0.003 (3)
C570.030 (3)0.029 (3)0.031 (4)0.002 (3)0.016 (3)0.007 (3)
C580.026 (3)0.035 (3)0.025 (3)−0.001 (2)0.013 (2)0.004 (3)
C590.021 (3)0.036 (3)0.028 (3)−0.006 (2)0.012 (2)−0.009 (3)
C600.019 (3)0.020 (3)0.028 (3)−0.005 (2)0.008 (2)0.004 (2)
O50.032 (2)0.016 (2)0.031 (2)0.0005 (17)0.0135 (17)0.0008 (18)
N90.024 (2)0.010 (2)0.032 (3)−0.001 (2)0.015 (2)−0.005 (2)
N100.031 (3)0.022 (3)0.036 (3)0.005 (2)0.021 (2)−0.001 (2)
C610.030 (3)0.029 (3)0.033 (3)0.002 (3)0.013 (3)−0.003 (3)
C620.016 (3)0.028 (3)0.027 (3)0.002 (3)0.012 (2)−0.003 (3)
C630.016 (3)0.030 (3)0.028 (3)0.000 (2)0.013 (2)0.001 (3)
C640.019 (3)0.019 (3)0.031 (3)−0.004 (2)0.008 (2)0.003 (3)
C650.021 (3)0.027 (3)0.026 (3)−0.002 (2)0.008 (2)−0.008 (3)
C660.014 (3)0.021 (3)0.030 (3)−0.004 (2)0.010 (2)−0.004 (3)
C670.023 (3)0.024 (3)0.032 (3)0.002 (2)0.015 (2)0.008 (3)
C680.017 (3)0.015 (3)0.036 (3)−0.008 (2)0.018 (3)−0.015 (3)
C690.020 (3)0.030 (3)0.022 (3)0.000 (2)0.007 (2)−0.003 (3)
C700.019 (3)0.026 (3)0.022 (3)−0.003 (2)0.009 (2)−0.002 (2)
C710.018 (3)0.032 (3)0.033 (3)0.007 (2)0.013 (2)−0.004 (3)
C720.031 (3)0.032 (3)0.027 (3)0.003 (3)0.013 (2)0.000 (2)
C730.025 (3)0.044 (4)0.023 (3)−0.002 (3)0.014 (2)0.002 (3)
C740.027 (3)0.033 (3)0.040 (4)0.005 (3)0.018 (3)0.014 (3)
C750.030 (3)0.017 (3)0.035 (4)−0.001 (2)0.022 (3)−0.002 (3)
O60.030 (2)0.029 (2)0.036 (2)−0.0012 (18)0.0143 (17)−0.0042 (19)
N110.025 (3)0.032 (3)0.033 (3)−0.002 (2)0.009 (2)−0.003 (2)
N120.023 (3)0.017 (3)0.035 (3)−0.002 (2)0.015 (2)−0.003 (2)
C760.032 (3)0.041 (3)0.027 (3)0.004 (3)0.012 (2)−0.005 (3)
C770.016 (3)0.017 (3)0.033 (3)0.003 (2)0.007 (2)0.000 (3)
C780.023 (3)0.021 (3)0.020 (3)0.004 (2)0.009 (2)−0.005 (2)
C790.024 (3)0.024 (3)0.033 (3)0.001 (2)0.014 (3)−0.008 (3)
C800.022 (3)0.018 (3)0.032 (3)−0.004 (2)0.010 (2)−0.008 (3)
C810.015 (3)0.021 (3)0.033 (3)−0.002 (2)0.012 (3)−0.009 (3)
C820.022 (3)0.023 (3)0.038 (3)−0.002 (2)0.017 (3)−0.008 (3)
C830.025 (3)0.022 (3)0.037 (4)−0.003 (2)0.016 (3)0.004 (3)
C840.021 (3)0.025 (3)0.042 (4)0.002 (2)0.019 (3)−0.008 (3)
C850.021 (3)0.024 (3)0.037 (3)−0.004 (2)0.016 (3)−0.006 (3)
C860.025 (3)0.016 (3)0.044 (4)0.005 (2)0.016 (3)0.005 (3)
C870.026 (3)0.033 (3)0.032 (3)0.005 (2)0.012 (2)−0.002 (3)
C880.034 (3)0.030 (3)0.036 (3)0.004 (3)0.019 (3)0.004 (3)
C890.034 (3)0.028 (3)0.040 (4)0.004 (3)0.022 (3)0.005 (3)
C900.029 (3)0.015 (3)0.045 (4)0.003 (2)0.020 (3)0.003 (3)
O1S0.026 (2)0.022 (2)0.028 (2)−0.0022 (17)0.0093 (18)0.0002 (16)
O2S0.027 (2)0.025 (2)0.029 (2)−0.0046 (16)0.0093 (18)−0.0038 (17)
O3S0.031 (2)0.023 (2)0.034 (2)−0.0034 (16)0.0147 (18)−0.0014 (16)
O4S0.039 (2)0.027 (2)0.035 (2)−0.0100 (18)0.0113 (18)−0.0014 (17)

Geometric parameters (Å, °)

O1—C21.227 (5)N8—C541.277 (6)
N1—C21.350 (6)N8—C551.427 (6)
N1—C31.407 (6)C46—C471.515 (6)
N1—H1N0.877 (17)C46—H46A0.9800
N2—C91.279 (6)C46—H46B0.9800
N2—C101.429 (6)C46—H46C0.9800
C1—C21.517 (6)C48—C531.390 (6)
C1—H1A0.9800C48—C491.392 (6)
C1—H1B0.9800C49—C501.368 (6)
C1—H1C0.9800C49—H490.9500
C3—C41.381 (6)C50—C511.410 (6)
C3—C81.403 (6)C50—H500.9500
C4—C51.370 (6)C51—C521.384 (6)
C4—H40.9500C51—C541.454 (6)
C5—C61.377 (6)C52—C531.384 (6)
C5—H50.9500C52—H520.9500
C6—C71.395 (6)C53—H530.9500
C6—C91.461 (7)C54—H540.9500
C7—C81.382 (6)C55—C561.379 (6)
C7—H70.9500C55—C601.410 (6)
C8—H80.9500C56—C571.381 (6)
C9—H90.9500C56—H560.9500
C10—C151.388 (6)C57—C581.393 (6)
C10—C111.415 (6)C57—H570.9500
C11—C121.383 (6)C58—C591.378 (6)
C11—H110.9500C58—H580.9500
C12—C131.385 (6)C59—C601.379 (6)
C12—H120.9500C59—H590.9500
C13—C141.386 (6)C60—H600.9500
C13—H130.9500O5—C621.222 (5)
C14—C151.382 (6)N9—C621.368 (6)
C14—H140.9500N9—C631.418 (6)
C15—H150.9500N9—H9N0.873 (17)
O2—C171.224 (5)N10—C691.280 (6)
N3—C171.368 (6)N10—C701.418 (6)
N3—C181.396 (6)C61—C621.499 (6)
N3—H3N0.868 (17)C61—H61A0.9800
N4—C241.286 (6)C61—H61B0.9800
N4—C251.427 (6)C61—H61C0.9800
C16—C171.485 (6)C63—C641.385 (6)
C16—H16A0.9800C63—C681.399 (6)
C16—H16B0.9800C64—C651.390 (6)
C16—H16C0.9800C64—H640.9500
C18—C191.400 (6)C65—C661.381 (6)
C18—C231.402 (6)C65—H650.9500
C19—C201.379 (6)C66—C671.393 (6)
C19—H190.9500C66—C691.449 (6)
C20—C211.394 (6)C67—C681.369 (6)
C20—H200.9500C67—H670.9500
C21—C221.381 (6)C68—H680.9500
C21—C241.452 (6)C69—H690.9500
C22—C231.396 (6)C70—C751.393 (6)
C22—H220.9500C70—C711.398 (6)
C23—H230.9500C71—C721.367 (6)
C24—H240.9500C71—H710.9500
C25—C261.397 (6)C72—C731.392 (6)
C25—C301.397 (6)C72—H720.9500
C26—C271.391 (7)C73—C741.386 (6)
C26—H260.9500C73—H730.9500
C27—C281.399 (6)C74—C751.367 (6)
C27—H270.9500C74—H740.9500
C28—C291.384 (6)C75—H750.9500
C28—H280.9500O6—C771.240 (5)
C29—C301.405 (6)N11—C771.353 (6)
C29—H290.9500N11—C781.396 (6)
C30—H300.9500N11—H11N0.867 (18)
O3—C321.242 (5)N12—C841.285 (6)
N5—C321.357 (6)N12—C851.406 (6)
N5—C331.401 (6)C76—C771.531 (6)
N5—H5N0.857 (17)C76—H76A0.9800
N6—C391.294 (6)C76—H76B0.9800
N6—C401.419 (6)C76—H76C0.9800
C31—C321.493 (6)C78—C831.395 (6)
C31—H31A0.9800C78—C791.402 (6)
C31—H31B0.9800C79—C801.374 (6)
C31—H31C0.9800C79—H790.9500
C33—C381.398 (6)C80—C811.406 (6)
C33—C341.404 (6)C80—H800.9500
C34—C351.364 (6)C81—C821.406 (6)
C34—H340.9500C81—C841.457 (6)
C35—C361.391 (6)C82—C831.370 (6)
C35—H350.9500C82—H820.9500
C36—C371.406 (6)C83—H830.9500
C36—C391.449 (6)C84—H840.9500
C37—C381.395 (6)C85—C861.392 (6)
C37—H370.9500C85—C901.399 (6)
C38—H380.9500C86—C871.377 (6)
C39—H390.9500C86—H860.9500
C40—C451.384 (6)C87—C881.381 (6)
C40—C411.398 (6)C87—H870.9500
C41—C421.382 (6)C88—C891.389 (6)
C41—H410.9500C88—H880.9500
C42—C431.383 (6)C89—C901.374 (6)
C42—H420.9500C89—H890.9500
C43—C441.389 (6)C90—H900.9500
C43—H430.9500O1S—H1O0.832 (19)
C44—C451.380 (6)O1S—H2O0.884 (18)
C44—H440.9500O2S—H3O0.845 (18)
C45—H450.9500O2S—H4O0.857 (19)
O4—C471.247 (5)O3S—H5O0.848 (18)
N7—C471.341 (6)O3S—H6O0.886 (18)
N7—C481.411 (6)O4S—H7O0.870 (19)
N7—H7N0.860 (18)O4S—H8O0.977 (19)
C2—N1—C3127.5 (4)C48—N7—H7N115 (3)
C2—N1—H1N117 (3)C54—N8—C55119.1 (4)
C3—N1—H1N116 (3)C47—C46—H46A109.5
C9—N2—C10119.5 (4)C47—C46—H46B109.5
C2—C1—H1A109.5H46A—C46—H46B109.5
C2—C1—H1B109.5C47—C46—H46C109.5
H1A—C1—H1B109.5H46A—C46—H46C109.5
C2—C1—H1C109.5H46B—C46—H46C109.5
H1A—C1—H1C109.5O4—C47—N7126.0 (4)
H1B—C1—H1C109.5O4—C47—C46118.9 (4)
O1—C2—N1124.4 (4)N7—C47—C46115.1 (4)
O1—C2—C1120.6 (4)C53—C48—C49118.2 (4)
N1—C2—C1115.0 (4)C53—C48—N7123.9 (4)
C4—C3—C8118.7 (4)C49—C48—N7117.8 (4)
C4—C3—N1125.8 (5)C50—C49—C48122.2 (4)
C8—C3—N1115.4 (5)C50—C49—H49118.9
C5—C4—C3119.9 (5)C48—C49—H49118.9
C5—C4—H4120.0C49—C50—C51119.4 (4)
C3—C4—H4120.0C49—C50—H50120.3
C4—C5—C6122.2 (5)C51—C50—H50120.3
C4—C5—H5118.9C52—C51—C50118.6 (4)
C6—C5—H5118.9C52—C51—C54118.4 (5)
C5—C6—C7118.6 (4)C50—C51—C54123.0 (5)
C5—C6—C9120.1 (5)C51—C52—C53121.3 (5)
C7—C6—C9121.4 (5)C51—C52—H52119.4
C8—C7—C6119.7 (5)C53—C52—H52119.4
C8—C7—H7120.1C52—C53—C48120.2 (5)
C6—C7—H7120.1C52—C53—H53119.9
C7—C8—C3120.8 (5)C48—C53—H53119.9
C7—C8—H8119.6N8—C54—C51124.5 (5)
C3—C8—H8119.6N8—C54—H54117.8
N2—C9—C6123.7 (5)C51—C54—H54117.8
N2—C9—H9118.1C56—C55—C60117.6 (4)
C6—C9—H9118.1C56—C55—N8119.9 (5)
C15—C10—C11119.3 (5)C60—C55—N8122.4 (5)
C15—C10—N2118.0 (5)C55—C56—C57122.6 (5)
C11—C10—N2122.6 (5)C55—C56—H56118.7
C12—C11—C10119.2 (5)C57—C56—H56118.7
C12—C11—H11120.4C56—C57—C58119.4 (5)
C10—C11—H11120.4C56—C57—H57120.3
C11—C12—C13120.9 (5)C58—C57—H57120.3
C11—C12—H12119.5C59—C58—C57118.6 (5)
C13—C12—H12119.5C59—C58—H58120.7
C12—C13—C14119.8 (5)C57—C58—H58120.7
C12—C13—H13120.1C58—C59—C60122.0 (5)
C14—C13—H13120.1C58—C59—H59119.0
C15—C14—C13120.1 (5)C60—C59—H59119.0
C15—C14—H14119.9C59—C60—C55119.6 (5)
C13—C14—H14119.9C59—C60—H60120.2
C14—C15—C10120.7 (5)C55—C60—H60120.2
C14—C15—H15119.7C62—N9—C63128.8 (4)
C10—C15—H15119.7C62—N9—H9N112 (3)
C17—N3—C18129.1 (4)C63—N9—H9N119 (3)
C17—N3—H3N119 (3)C69—N10—C70119.4 (5)
C18—N3—H3N112 (3)C62—C61—H61A109.5
C24—N4—C25118.2 (4)C62—C61—H61B109.5
C17—C16—H16A109.5H61A—C61—H61B109.5
C17—C16—H16B109.5C62—C61—H61C109.5
H16A—C16—H16B109.5H61A—C61—H61C109.5
C17—C16—H16C109.5H61B—C61—H61C109.5
H16A—C16—H16C109.5O5—C62—N9122.7 (5)
H16B—C16—H16C109.5O5—C62—C61122.2 (5)
O2—C17—N3122.9 (4)N9—C62—C61115.1 (4)
O2—C17—C16122.9 (5)C64—C63—C68119.2 (4)
N3—C17—C16114.1 (4)C64—C63—N9125.3 (5)
N3—C18—C19118.4 (4)C68—C63—N9115.5 (5)
N3—C18—C23123.0 (4)C63—C64—C65118.8 (5)
C19—C18—C23118.6 (4)C63—C64—H64120.6
C20—C19—C18121.0 (5)C65—C64—H64120.6
C20—C19—H19119.5C66—C65—C64122.9 (5)
C18—C19—H19119.5C66—C65—H65118.6
C19—C20—C21121.3 (5)C64—C65—H65118.6
C19—C20—H20119.4C65—C66—C67117.1 (4)
C21—C20—H20119.4C65—C66—C69122.9 (5)
C22—C21—C20117.4 (4)C67—C66—C69120.0 (5)
C22—C21—C24119.5 (5)C68—C67—C66121.4 (5)
C20—C21—C24123.1 (5)C68—C67—H67119.3
C21—C22—C23122.9 (5)C66—C67—H67119.3
C21—C22—H22118.5C67—C68—C63120.6 (5)
C23—C22—H22118.5C67—C68—H68119.7
C22—C23—C18118.8 (5)C63—C68—H68119.7
C22—C23—H23120.6N10—C69—C66122.9 (5)
C18—C23—H23120.6N10—C69—H69118.5
N4—C24—C21124.4 (5)C66—C69—H69118.5
N4—C24—H24117.8C75—C70—C71119.0 (5)
C21—C24—H24117.8C75—C70—N10117.0 (5)
C26—C25—C30120.5 (5)C71—C70—N10123.9 (5)
C26—C25—N4117.3 (5)C72—C71—C70120.3 (5)
C30—C25—N4121.9 (5)C72—C71—H71119.9
C27—C26—C25119.5 (5)C70—C71—H71119.9
C27—C26—H26120.2C71—C72—C73120.3 (5)
C25—C26—H26120.2C71—C72—H72119.9
C26—C27—C28120.5 (5)C73—C72—H72119.9
C26—C27—H27119.7C74—C73—C72119.6 (5)
C28—C27—H27119.7C74—C73—H73120.2
C29—C28—C27119.7 (5)C72—C73—H73120.2
C29—C28—H28120.1C75—C74—C73120.3 (5)
C27—C28—H28120.1C75—C74—H74119.9
C28—C29—C30120.6 (5)C73—C74—H74119.9
C28—C29—H29119.7C74—C75—C70120.6 (5)
C30—C29—H29119.7C74—C75—H75119.7
C25—C30—C29119.1 (5)C70—C75—H75119.7
C25—C30—H30120.4C77—N11—C78128.0 (4)
C29—C30—H30120.4C77—N11—H11N115 (3)
C32—N5—C33130.9 (4)C78—N11—H11N117 (3)
C32—N5—H5N115 (3)C84—N12—C85119.5 (5)
C33—N5—H5N113 (3)C77—C76—H76A109.5
C39—N6—C40119.6 (4)C77—C76—H76B109.5
C32—C31—H31A109.5H76A—C76—H76B109.5
C32—C31—H31B109.5C77—C76—H76C109.5
H31A—C31—H31B109.5H76A—C76—H76C109.5
C32—C31—H31C109.5H76B—C76—H76C109.5
H31A—C31—H31C109.5O6—C77—N11125.5 (5)
H31B—C31—H31C109.5O6—C77—C76120.4 (5)
O3—C32—N5121.9 (5)N11—C77—C76114.0 (4)
O3—C32—C31122.5 (5)C83—C78—N11115.8 (5)
N5—C32—C31115.6 (4)C83—C78—C79120.2 (5)
C38—C33—N5123.4 (5)N11—C78—C79124.0 (5)
C38—C33—C34118.8 (5)C80—C79—C78117.9 (5)
N5—C33—C34117.7 (4)C80—C79—H79121.1
C35—C34—C33120.1 (5)C78—C79—H79121.1
C35—C34—H34120.0C79—C80—C81122.9 (5)
C33—C34—H34120.0C79—C80—H80118.6
C34—C35—C36122.5 (5)C81—C80—H80118.6
C34—C35—H35118.8C80—C81—C82117.8 (5)
C36—C35—H35118.8C80—C81—C84122.0 (5)
C35—C36—C37117.8 (4)C82—C81—C84120.2 (5)
C35—C36—C39124.0 (5)C83—C82—C81120.0 (5)
C37—C36—C39118.2 (5)C83—C82—H82120.0
C38—C37—C36120.4 (5)C81—C82—H82120.0
C38—C37—H37119.8C82—C83—C78121.1 (5)
C36—C37—H37119.8C82—C83—H83119.4
C37—C38—C33120.4 (5)C78—C83—H83119.4
C37—C38—H38119.8N12—C84—C81122.1 (5)
C33—C38—H38119.8N12—C84—H84119.0
N6—C39—C36122.7 (5)C81—C84—H84119.0
N6—C39—H39118.6C86—C85—C90118.3 (5)
C36—C39—H39118.6C86—C85—N12123.3 (5)
C45—C40—C41118.2 (5)C90—C85—N12118.2 (5)
C45—C40—N6124.5 (5)C87—C86—C85120.8 (5)
C41—C40—N6117.2 (5)C87—C86—H86119.6
C42—C41—C40120.9 (5)C85—C86—H86119.6
C42—C41—H41119.6C86—C87—C88120.3 (5)
C40—C41—H41119.6C86—C87—H87119.8
C41—C42—C43120.2 (5)C88—C87—H87119.8
C41—C42—H42119.9C87—C88—C89119.7 (5)
C43—C42—H42119.9C87—C88—H88120.2
C42—C43—C44119.3 (5)C89—C88—H88120.2
C42—C43—H43120.3C90—C89—C88120.1 (5)
C44—C43—H43120.3C90—C89—H89120.0
C45—C44—C43120.3 (5)C88—C89—H89120.0
C45—C44—H44119.8C89—C90—C85120.8 (5)
C43—C44—H44119.8C89—C90—H90119.6
C44—C45—C40121.1 (5)C85—C90—H90119.6
C44—C45—H45119.5H1O—O1S—H2O114 (4)
C40—C45—H45119.5H3O—O2S—H4O97 (4)
C47—N7—C48127.3 (4)H5O—O3S—H6O102 (4)
C47—N7—H7N117 (3)H7O—O4S—H8O100 (4)
C3—N1—C2—O13.4 (8)C48—N7—C47—O44.7 (8)
C3—N1—C2—C1−175.3 (4)C48—N7—C47—C46−176.3 (4)
C2—N1—C3—C43.3 (8)C47—N7—C48—C5313.3 (8)
C2—N1—C3—C8179.8 (4)C47—N7—C48—C49−169.6 (4)
C8—C3—C4—C52.1 (7)C53—C48—C49—C50−3.6 (7)
N1—C3—C4—C5178.5 (5)N7—C48—C49—C50179.2 (4)
C3—C4—C5—C6−0.4 (8)C48—C49—C50—C510.3 (7)
C4—C5—C6—C7−0.8 (8)C49—C50—C51—C522.9 (7)
C4—C5—C6—C9179.2 (5)C49—C50—C51—C54−179.0 (4)
C5—C6—C7—C80.2 (7)C50—C51—C52—C53−2.8 (7)
C9—C6—C7—C8−179.8 (4)C54—C51—C52—C53178.9 (5)
C6—C7—C8—C31.6 (7)C51—C52—C53—C48−0.4 (8)
C4—C3—C8—C7−2.7 (7)C49—C48—C53—C523.6 (7)
N1—C3—C8—C7−179.5 (4)N7—C48—C53—C52−179.3 (4)
C10—N2—C9—C6177.3 (5)C55—N8—C54—C51177.2 (5)
C5—C6—C9—N2179.9 (5)C52—C51—C54—N8178.1 (5)
C7—C6—C9—N2−0.1 (8)C50—C51—C54—N8−0.1 (8)
C9—N2—C10—C15141.4 (5)C54—N8—C55—C56136.3 (5)
C9—N2—C10—C11−42.8 (7)C54—N8—C55—C60−46.3 (7)
C15—C10—C11—C120.2 (7)C60—C55—C56—C570.5 (7)
N2—C10—C11—C12−175.6 (5)N8—C55—C56—C57178.0 (5)
C10—C11—C12—C13−0.1 (7)C55—C56—C57—C58−1.8 (8)
C11—C12—C13—C14−0.6 (8)C56—C57—C58—C591.1 (7)
C12—C13—C14—C151.2 (8)C57—C58—C59—C601.0 (7)
C13—C14—C15—C10−1.1 (8)C58—C59—C60—C55−2.4 (7)
C11—C10—C15—C140.4 (7)C56—C55—C60—C591.6 (7)
N2—C10—C15—C14176.3 (5)N8—C55—C60—C59−175.8 (5)
C18—N3—C17—O2−3.6 (8)C63—N9—C62—O5−3.4 (8)
C18—N3—C17—C16174.1 (5)C63—N9—C62—C61175.7 (4)
C17—N3—C18—C19166.2 (5)C62—N9—C63—C6417.4 (8)
C17—N3—C18—C23−13.3 (8)C62—N9—C63—C68−164.6 (4)
N3—C18—C19—C20−178.6 (4)C68—C63—C64—C650.5 (7)
C23—C18—C19—C200.9 (7)N9—C63—C64—C65178.4 (5)
C18—C19—C20—C211.2 (7)C63—C64—C65—C66−1.4 (8)
C19—C20—C21—C22−2.2 (7)C64—C65—C66—C671.3 (7)
C19—C20—C21—C24177.7 (4)C64—C65—C66—C69−178.1 (5)
C20—C21—C22—C231.1 (7)C65—C66—C67—C68−0.5 (7)
C24—C21—C22—C23−178.8 (5)C69—C66—C67—C68179.0 (5)
C21—C22—C23—C181.0 (8)C66—C67—C68—C63−0.3 (7)
N3—C18—C23—C22177.5 (4)C64—C63—C68—C670.3 (7)
C19—C18—C23—C22−2.0 (7)N9—C63—C68—C67−177.8 (4)
C25—N4—C24—C21−176.9 (5)C70—N10—C69—C66176.9 (5)
C22—C21—C24—N4−175.6 (5)C65—C66—C69—N10169.5 (5)
C20—C21—C24—N44.6 (8)C67—C66—C69—N10−9.9 (8)
C24—N4—C25—C26−136.0 (5)C69—N10—C70—C75140.5 (5)
C24—N4—C25—C3048.7 (7)C69—N10—C70—C71−43.5 (7)
C30—C25—C26—C27−0.8 (7)C75—C70—C71—C72−0.7 (8)
N4—C25—C26—C27−176.1 (4)N10—C70—C71—C72−176.7 (5)
C25—C26—C27—C280.8 (8)C70—C71—C72—C73−0.8 (8)
C26—C27—C28—C29−0.5 (8)C71—C72—C73—C740.9 (8)
C27—C28—C29—C300.2 (8)C72—C73—C74—C750.6 (8)
C26—C25—C30—C290.5 (7)C73—C74—C75—C70−2.2 (8)
N4—C25—C30—C29175.6 (4)C71—C70—C75—C742.2 (8)
C28—C29—C30—C25−0.2 (7)N10—C70—C75—C74178.5 (5)
C33—N5—C32—O3−5.6 (8)C78—N11—C77—O61.1 (8)
C33—N5—C32—C31174.5 (5)C78—N11—C77—C76−180.0 (4)
C32—N5—C33—C384.7 (8)C77—N11—C78—C83165.0 (5)
C32—N5—C33—C34−178.3 (5)C77—N11—C78—C79−16.0 (8)
C38—C33—C34—C35−0.3 (7)C83—C78—C79—C80−0.5 (7)
N5—C33—C34—C35−177.5 (4)N11—C78—C79—C80−179.5 (5)
C33—C34—C35—C360.4 (7)C78—C79—C80—C812.1 (7)
C34—C35—C36—C37−0.4 (7)C79—C80—C81—C82−2.2 (7)
C34—C35—C36—C39179.5 (5)C79—C80—C81—C84178.0 (5)
C35—C36—C37—C380.2 (7)C80—C81—C82—C830.7 (7)
C39—C36—C37—C38−179.6 (4)C84—C81—C82—C83−179.5 (4)
C36—C37—C38—C33−0.2 (7)C81—C82—C83—C780.8 (7)
N5—C33—C38—C37177.2 (5)N11—C78—C83—C82178.2 (4)
C34—C33—C38—C370.2 (7)C79—C78—C83—C82−0.9 (7)
C40—N6—C39—C36−178.1 (5)C85—N12—C84—C81−177.8 (5)
C35—C36—C39—N61.7 (8)C80—C81—C84—N12−172.3 (5)
C37—C36—C39—N6−178.5 (4)C82—C81—C84—N127.9 (7)
C39—N6—C40—C4542.9 (7)C84—N12—C85—C8640.9 (7)
C39—N6—C40—C41−140.8 (5)C84—N12—C85—C90−143.9 (5)
C45—C40—C41—C42−1.2 (7)C90—C85—C86—C871.3 (7)
N6—C40—C41—C42−177.7 (4)N12—C85—C86—C87176.5 (5)
C40—C41—C42—C431.7 (8)C85—C86—C87—C880.5 (8)
C41—C42—C43—C44−1.6 (8)C86—C87—C88—C89−1.2 (8)
C42—C43—C44—C451.1 (7)C87—C88—C89—C90−0.1 (8)
C43—C44—C45—C40−0.7 (7)C88—C89—C90—C851.9 (8)
C41—C40—C45—C440.7 (7)C86—C85—C90—C89−2.5 (8)
N6—C40—C45—C44176.9 (5)N12—C85—C90—C89−178.0 (5)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1N···O1S0.88 (2)2.00 (2)2.872 (5)173 (4)
N3—H3N···O2S0.87 (2)1.99 (2)2.859 (5)173 (4)
N5—H5N···O4S0.86 (2)2.09 (2)2.919 (5)163 (4)
N7—H7N···O3S0.86 (2)2.03 (2)2.858 (5)161 (4)
N9—H9N···O40.87 (2)2.10 (2)2.929 (5)158 (4)
N11—H11N···O20.87 (2)2.16 (3)2.947 (5)151 (4)
O1S—H1O···N40.83 (2)2.29 (3)2.939 (5)136 (4)
O1S—H2O···O50.88 (2)1.88 (2)2.764 (5)173 (4)
O2S—H3O···N20.85 (2)2.16 (2)3.006 (5)177 (4)
O2S—H4O···O30.86 (2)1.96 (2)2.781 (5)160 (5)
O3S—H5O···N6i0.85 (2)2.33 (3)3.001 (5)136 (3)
O3S—H6O···O1i0.89 (2)1.90 (2)2.778 (4)172 (4)
O4S—H7O···N8ii0.87 (2)2.09 (2)2.954 (5)171 (4)
O4S—H8O···O6ii0.98 (2)1.76 (2)2.726 (5)170 (4)

Symmetry codes: (i) x, y+1, z; (ii) x, y−1, z.

Table 2 Dihedral angles (°) between the aromatic rings in each molecule of (I)

Plane–planeDihedral angle
P1–P242.4 (2)
P3–P452.8 (2)
P5–P643.7 (2)
P7–P848.0 (2)
P9–P1053.8 (2)
P11–P1248.1 (2)

Planes P1–P12 are those through the C3–C9, C10–C15, C18–C23, C25–C30, C33–C38, C40–C45, C48–C53, C55–C60, C63–C68, C70–C75, C78–C83 and C85-C90 rings, respectively.

Table 3 Intermolecular distances (Å) of the atoms of the carbonyl groups to the aromatic ring between the paired molecules

Atom···planeDistances
O1···P5, C2···P53.375 (4), 3.427 (6)
O2···P9, C17···P93.061 (4), 3.191 (6)
O3···P1, C32···P13.421 (4), 3.492 (6)
O4···P11, C47···P113.073 (4), 3.236 (6)
O5···P3, C62···P33.002 (4), 3.448 (6)
O6···P7, C77···P73.036 (4), 3.470 (6)

Planes P1, P3, P5, P7, P9 and P11 are those through the C3–C9, C18–C23, C33–C38, C48–C53, C63–C68 and C78–C83 rings, respectively.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5642).

References

  • Aoyama, Y., Fujisawa, T., Watanabe, T., Toi, H. & Ogoshi, H. (1986). J. Am. Chem. Soc.108, 943–947.
  • Bruker (2001). SMART Bruker AXS Inc., Madison, Wisconsin, USA.
  • Bruker (2002). SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Dixit, N., Mishra, L., Mustafi, S. M., Chary, K. V. R. & Houjou, H. (2009). Spectrochim. Acta A, 73 , 29–34. [PubMed]
  • Kureshy, R. I., Khan, N. H., Abdi, S. H. R., Patel, S. T. & Iyer, P. (1999). J. Mol. Catal.150, 175–183.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Souza, P., Garcia-Vazquez, J. A. & Masaguer, J. R. (1985). Transition Met. Chem.10, 410–412.
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography