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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 65| Part 1| January 2009| Pages o17-o18

N′-[(E)-1-(4-Chloro­phen­yl)ethyl­­idene]-2-[4-(2-methyl­prop­yl)phen­yl]propano­hydrazide

aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore 574 199, India
*Correspondence e-mail: hkfun@usm.my

(Received 12 November 2008; accepted 21 November 2008; online 3 December 2008)

The asymmetric unit of the title compound, C21H25ClN2O, contains four crystallographically independent mol­ecules, which differ mainly in the orientation of the isobutyl groups. The benzene rings are almost orthogonal to each other, forming dihedral angles of 87.40 (6), 88.69 (6), 84.88 (6) and 85.12 (6)° in the four mol­ecules. The crystal structure is stabilized by inter­molecular N—H⋯O and C—H⋯O hydrogen bonds, together with C—H⋯π inter­actions.

Related literature

For the synthesis of pyrazolines and pyrazoles, see: Sridhar & Perumal (2003[Sridhar, R. & Perumal, T. (2003). Synth. Commun. 33, 1483-1488.]). For the pharmaceutical applications of hydrazones, see: Bedia et al. (2006[Bedia, K.-K., Elçin, O., Seda, U., Fatma, K., Nathaly, S., Sevim, R. & Dimoglo, A. (2006). Eur. J. Med. Chem. 41, 1253-1261.]); Rollas et al. (2002[Rollas, S., Gülerman, N. & Erdeniz, H. (2002). Farmaco, 57, 171-174.]); Terzioglu & Gursoy (2003[Terzioglu, N. & Gursoy, A. (2003). Eur. J. Med. Chem. 38, 781-786.]). For related literature on ibuprofen, see: Amir & Kumar (2007[Amir, M. & Kumar, S. (2007). Acta Pharm. 57, 31-45.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C21H25ClN2O

  • Mr = 356.88

  • Triclinic, [P \overline 1]

  • a = 14.2691 (2) Å

  • b = 15.5343 (2) Å

  • c = 20.7436 (3) Å

  • α = 77.416 (1)°

  • β = 90.058 (1)°

  • γ = 62.714 (1)°

  • V = 3961.17 (10) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.20 mm−1

  • T = 100.0 (1) K

  • 0.54 × 0.18 × 0.17 mm

Data collection
  • Bruker SMART APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.899, Tmax = 0.966

  • 132549 measured reflections

  • 28009 independent reflections

  • 19617 reflections with I > 2σ(I)

  • Rint = 0.040

Refinement
  • R[F2 > 2σ(F2)] = 0.065

  • wR(F2) = 0.166

  • S = 1.08

  • 28009 reflections

  • 933 parameters

  • 4 restraints

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

  • Δρmax = 0.65 e Å−3

  • Δρmin = −0.28 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2, Cg3 and Cg4 are the centroids of the C10A–C15A, C10B–C15B, C10C–C15C and C10D–C15D rings, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
N2A—H2NA⋯O1Bi 0.847 (14) 2.090 (17) 2.9255 (19) 169 (3)
N2B—H2NB⋯O1Ai 0.852 (18) 2.069 (18) 2.916 (2) 173 (2)
N2C—H2NC⋯O1Dii 0.845 (15) 2.075 (17) 2.9085 (19) 169 (3)
N2D—H2ND⋯O1Ciii 0.855 (16) 2.085 (17) 2.934 (2) 172 (3)
C20B—H20A⋯O1Ai 0.96 2.47 3.125 (3) 126
C20C—H20D⋯O1Dii 0.96 2.57 3.099 (3) 115
C20D—H20G⋯O1Cii 0.96 2.50 3.175 (3) 128
C2OA—H2OCCg1iv 0.96 2.75 3.4628 (19) 131
C16C—H16FCg2 0.96 2.78 3.744 (2) 171
C20B—H20CCg2i 0.96 2.94 3.5787 (19) 125
C16A—H16BCg3v 0.96 2.90 3.860 (2) 170
C20C—H20FCg3ii 0.96 2.77 3.4943 (19) 132
C16B—H16DCg4 0.96 2.86 3.818 (2) 171
C20D—H20ICg4vi 0.96 2.96 3.5557 (19) 122
Symmetry codes: (i) -x+1, -y+2, -z+2; (ii) -x+2, -y+1, -z+1; (iii) -x+2, -y+1, -z+1; (iv) -x, -y+2, -z+2; (v) x-1, y, z; (vi) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]).

Supporting information


Comment top

Aryl hydrazones are important building blocks for the synthesis of a variety of heterocyclic compounds such as pyrazolines and pyrazoles (Sridhar & Perumal, 2003). Aryl hydrazones have been most conveniently synthesized by the reaction of aryl hydrazines with carbonyl compounds. The reaction has been performed in a variety of solvents such as ethanol, acetic acid, dioxan, diglyme, DMF and others with or without an acidic catalyst. Hydrazones possessing an azometine –NHNCH– group constitute an important class of compounds for new drug development. Therefore many researchers have synthesized these compounds as target structures and evaluated their biological activities. Hydrazones have been demonstrated to possess antimicrobial, anticonvulsant, analgesic, anti-inflammatory, antiplatelet, antitubercular, anticancer and antitumoral activities (Bedia et al., 2006; Rollas et al., 2002; Terzioglu & Gursoy, 2003). These observations have been the guide for the development of new hydrazones that possess various biological activities. Similarly ibuprofen is also known for its pharmaceutical activities and belongs to the class of non-steroidal anti-inflammatory Drugs (Amir & Kumar, 2007). Prompted by these review, the title compound was synthesized and its crystal structure is reported here.

The asymmetric unit of the title compound (Fig. 1) contains four crystallographically independent molecules (A, B, C & D) with similar geometries, the main difference consisting in the orientation of the isobutyl groups. Bond lengths (Allen et al., 1987) and angles have normal values. The benzene rings in each molecule are almost orthogonal to each other, as indicated by the dihedral angles of 87.40 (6)° (C1A—C6A; C10A—C15A), 88.69 (6)° (C1B—C6B; C10B—C15B), 84.88 (6)° (C1C—C6C; C10C—C15C) and 85.12 (6)° (C1D—C6D; C10D—C15D). The crystal structure (Fig. 2) is stabilized by intermolecular N—H···O and C—H···O hydrogen bonds together with C—H···π interactions (Table 1).

It is worth noting that the unit cell adopted in the present structure analysis is a superstructure of a fundamental monoclinic unit cell (cell 2) with half of the volume of the experimentally determined triclinic cell (cell 1). The two cells are related by the following transformation matrix: [a, b, c]cell 2 = [1/2, 1, 0, 1/2, 0 0, 0,0, 1] [a, b, c]cell 1. The dimensions of the fundamental cell are: a = 13.8052 (2), b = 7.1345 (2), c = 20.7436 (3) Å, β = 104.224 (1)°; space group P21/n. Solution and refinement of the structure in cell 2 were not successful.

Related literature top

For the synthesis of pyrazolines and pyrazoles, see: Sridhar & Perumal (2003). For the pharmaceutical applications of hydrazones, see: Bedia et al. (2006); Rollas et al. (2002); Terzioglu & Gursoy (2003). For related literature on ibuprofen, see: Amir & Kumar (2007). For bond-length data, see: Allen et al. (1987). Cg1, Cg2, Cg3 and Cg4 are the centroids of the C10A–C15A, C10B–C15B, C10C–C15C and C10D–C15D rings, respectively

Experimental top

The title compound was obtained by refluxing 2-[4-(2-methylpropyl)phenyl]propanehydrazide (0.01 mol) and 4-chloroacetophenone (0.01 mol) in ethanol (30 ml) by adding 3 drops of concentrated sulfuric acid for 1 h. Excess ethanol was removed from the reaction mixture under reduced pressure. The solid product obtained was filtered, washed with ethanol and dried. Crystals suitable for X-ray analysis were obtained by slow evaporation of an ethanol solution (yield 87%; m.p.418 K, MW 356).

Refinement top

N-bound H atoms were located in a difference map and were refined with the N—H bond lengths restrained to 0.85 (1) Å. Other H atoms were positioned geometrically and refined using a riding model, with C—H=0.93–0.98 Å and with Uiso(H) = 1.2 Ueq(C) or 1.5 Ueq(C) for methyl H atoms. A rotating-group model was used for the methyl groups.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom numbering scheme.
[Figure 2] Fig. 2. The crystal packing of the title compound, viewed down the c axis. Intermolecular hydrogen bonds are shown as dashed lines.
N'-[(E)-1-(4-Chlorophenyl)ethylidene]-2-[4-(2- methylpropyl)phenyl]propanohydrazide top
Crystal data top
C21H25ClN2OZ = 8
Mr = 356.88F(000) = 1520
Triclinic, P1Dx = 1.197 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 14.2691 (2) ÅCell parameters from 9864 reflections
b = 15.5343 (2) Åθ = 2.7–32.1°
c = 20.7436 (3) ŵ = 0.20 mm1
α = 77.416 (1)°T = 100 K
β = 90.058 (1)°Block, colourless
γ = 62.714 (1)°0.54 × 0.18 × 0.17 mm
V = 3961.17 (10) Å3
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
28009 independent reflections
Radiation source: fine-focus sealed tube19617 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.040
ϕ and ω scansθmax = 32.3°, θmin = 1.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
h = 2021
Tmin = 0.899, Tmax = 0.966k = 2323
132549 measured reflectionsl = 3131
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)] = 0.065Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.166H atoms treated by a mixture of independent and constrained refinement
S = 1.08 w = 1/[σ2(Fo2) + (0.0489P)2 + 3.7993P]
where P = (Fo2 + 2Fc2)/3
28009 reflections(Δ/σ)max = 0.001
933 parametersΔρmax = 0.65 e Å3
4 restraintsΔρmin = 0.29 e Å3
Crystal data top
C21H25ClN2Oγ = 62.714 (1)°
Mr = 356.88V = 3961.17 (10) Å3
Triclinic, P1Z = 8
a = 14.2691 (2) ÅMo Kα radiation
b = 15.5343 (2) ŵ = 0.20 mm1
c = 20.7436 (3) ÅT = 100 K
α = 77.416 (1)°0.54 × 0.18 × 0.17 mm
β = 90.058 (1)°
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
28009 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
19617 reflections with I > 2σ(I)
Tmin = 0.899, Tmax = 0.966Rint = 0.040
132549 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0654 restraints
wR(F2) = 0.166H atoms treated by a mixture of independent and constrained refinement
S = 1.08Δρmax = 0.65 e Å3
28009 reflectionsΔρmin = 0.29 e Å3
933 parameters
Special details top

Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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
Cl1A0.50215 (4)1.34130 (4)0.82547 (3)0.03036 (11)
O1A0.29382 (10)0.96358 (10)0.92933 (6)0.0218 (2)
N1A0.01803 (11)1.09790 (10)0.91770 (7)0.0160 (2)
N2A0.12260 (11)1.04811 (10)0.94423 (7)0.0158 (2)
C1A0.18634 (14)1.22066 (13)0.85444 (8)0.0194 (3)
H1AA0.13091.20900.82830.023*
C2A0.28962 (14)1.26671 (13)0.82420 (9)0.0209 (3)
H2AA0.30371.28600.77810.025*
C3A0.37220 (14)1.28381 (13)0.86357 (9)0.0201 (3)
C4A0.35268 (14)1.25639 (13)0.93217 (9)0.0201 (3)
H4AA0.40851.26850.95800.024*
C5A0.24866 (13)1.21050 (12)0.96211 (8)0.0176 (3)
H5AA0.23521.19231.00830.021*
C6A0.16400 (13)1.19132 (11)0.92377 (8)0.0151 (3)
C7A0.05227 (13)1.13919 (11)0.95537 (8)0.0153 (3)
C8A0.20007 (13)1.00697 (12)0.90573 (8)0.0160 (3)
C9A0.16750 (13)1.01376 (12)0.83402 (8)0.0161 (3)
H9AA0.09801.07260.81870.019*
C10A0.15797 (13)0.92062 (12)0.83157 (7)0.0159 (3)
C11A0.06320 (14)0.92817 (13)0.80610 (8)0.0205 (3)
H11A0.00510.99090.79010.025*
C12A0.05463 (16)0.84261 (14)0.80440 (9)0.0238 (3)
H12A0.00900.84940.78670.029*
C13A0.13929 (16)0.74756 (14)0.82873 (8)0.0227 (3)
C14A0.23477 (15)0.74057 (13)0.85333 (9)0.0221 (3)
H14A0.29310.67790.86900.027*
C15A0.24412 (14)0.82537 (12)0.85485 (8)0.0185 (3)
H15A0.30830.81860.87150.022*
C16A0.12727 (18)0.65540 (15)0.82993 (10)0.0288 (4)
H16A0.19670.60040.82910.035*
H16B0.08320.66770.78990.035*
C17A0.07800 (17)0.62367 (15)0.89080 (10)0.0279 (4)
H17A0.01000.68080.89300.033*
C18A0.1489 (2)0.59176 (18)0.95570 (11)0.0389 (5)
H18A0.11480.57400.99230.058*
H18B0.16070.64600.96100.058*
H18C0.21560.53520.95460.058*
C19A0.0569 (2)0.53832 (17)0.88258 (12)0.0392 (5)
H19A0.01130.55920.84210.059*
H19B0.02330.52090.91960.059*
H19C0.12300.48130.88090.059*
C2OA0.02665 (13)1.13534 (13)1.02674 (8)0.0182 (3)
H2OA0.02431.15911.02930.027*
H2OB0.00241.06771.05290.027*
H2OC0.09031.17671.04350.027*
C21A0.24880 (15)1.02591 (14)0.78999 (9)0.0229 (3)
H21A0.25461.08360.79440.034*
H21B0.22611.03430.74440.034*
H21C0.31660.96750.80350.034*
Cl1B0.01617 (4)1.34985 (4)0.82882 (3)0.03232 (11)
O1B0.78289 (10)0.97763 (10)0.92321 (6)0.0212 (2)
N1B0.50620 (11)1.10321 (10)0.91489 (7)0.0165 (3)
N2B0.61177 (11)1.05501 (11)0.94034 (7)0.0167 (3)
C1B0.29988 (15)1.22571 (14)0.85348 (8)0.0218 (3)
H1BA0.35431.21360.82650.026*
C2B0.19567 (15)1.27267 (14)0.82468 (9)0.0244 (4)
H2BA0.18011.29170.77860.029*
C3B0.11476 (14)1.29114 (13)0.86498 (9)0.0214 (3)
C4B0.13641 (14)1.26365 (14)0.93363 (9)0.0224 (3)
H4BA0.08151.27670.96030.027*
C5B0.24147 (14)1.21619 (13)0.96217 (8)0.0202 (3)
H5BA0.25641.19761.00820.024*
C6B0.32483 (13)1.19603 (12)0.92300 (8)0.0160 (3)
C7B0.43685 (13)1.14461 (12)0.95318 (8)0.0157 (3)
C8B0.68886 (13)1.01664 (12)0.90082 (8)0.0158 (3)
C9B0.65608 (13)1.01972 (12)0.83002 (8)0.0162 (3)
H9BA0.58341.07380.81580.019*
C10B0.65861 (13)0.92095 (12)0.82936 (7)0.0154 (3)
C11B0.56975 (14)0.91906 (12)0.80348 (8)0.0183 (3)
H11B0.50750.97860.78770.022*
C12B0.57317 (15)0.82861 (13)0.80093 (9)0.0217 (3)
H12B0.51350.82880.78260.026*
C13B0.66450 (15)0.73792 (13)0.82544 (8)0.0200 (3)
C14B0.75330 (14)0.74044 (13)0.85116 (9)0.0208 (3)
H14B0.81520.68090.86760.025*
C15B0.75094 (14)0.83051 (12)0.85259 (8)0.0185 (3)
H15B0.81150.83050.86920.022*
C16B0.66861 (17)0.63894 (13)0.82619 (9)0.0245 (4)
H16C0.73880.59350.81750.029*
H16D0.61800.64880.79050.029*
C17B0.64403 (16)0.59068 (14)0.89191 (9)0.0253 (4)
H17B0.68870.58950.92830.030*
C18B0.52867 (19)0.65016 (18)0.90218 (13)0.0390 (5)
H18D0.51280.71790.90010.059*
H18E0.51640.62090.94490.059*
H18F0.48380.64940.86800.059*
C19B0.6697 (2)0.48320 (15)0.89375 (12)0.0372 (5)
H19D0.74330.44560.88850.056*
H19E0.62650.48300.85830.056*
H19F0.65540.45340.93560.056*
C20B0.46283 (14)1.14388 (14)1.02360 (8)0.0206 (3)
H20A0.52091.15871.02590.031*
H20B0.48231.07911.05200.031*
H20C0.40191.19331.03790.031*
C21B0.73054 (16)1.04037 (14)0.78289 (9)0.0233 (3)
H21D0.70931.04260.73840.035*
H21E0.80210.98810.79670.035*
H21F0.72671.10330.78410.035*
Cl1C0.83776 (4)0.15525 (4)0.67181 (3)0.03310 (11)
O1C1.25756 (10)0.53449 (10)0.57579 (6)0.0220 (2)
N1C1.11575 (11)0.39962 (10)0.58593 (7)0.0164 (3)
N2C1.17065 (11)0.45005 (11)0.56011 (7)0.0168 (3)
C1C1.03591 (14)0.27335 (13)0.64667 (8)0.0189 (3)
H1CA1.08070.28290.67360.023*
C2C0.97822 (14)0.22643 (13)0.67556 (9)0.0213 (3)
H2CA0.98440.20460.72160.026*
C3C0.91144 (14)0.21232 (13)0.63540 (9)0.0208 (3)
C4C0.90208 (14)0.24352 (13)0.56681 (9)0.0212 (3)
H4CA0.85730.23340.54020.025*
C5C0.96042 (13)0.29019 (12)0.53803 (8)0.0183 (3)
H5CA0.95480.31080.49200.022*
C6C1.02740 (13)0.30639 (12)0.57749 (8)0.0158 (3)
C7C1.08685 (13)0.35933 (12)0.54719 (8)0.0156 (3)
C8C1.20567 (13)0.49209 (12)0.59893 (8)0.0163 (3)
C9C1.17627 (13)0.48785 (12)0.66953 (8)0.0166 (3)
H9CA1.16470.42960.68480.020*
C10C1.07335 (13)0.58187 (12)0.66935 (7)0.0154 (3)
C11C0.98370 (14)0.57633 (13)0.69243 (8)0.0190 (3)
H11C0.98650.51420.70780.023*
C12C0.89064 (14)0.66244 (13)0.69266 (8)0.0216 (3)
H12C0.83240.65690.70880.026*
C13C0.88253 (14)0.75716 (13)0.66922 (8)0.0209 (3)
C14C0.97276 (15)0.76233 (13)0.64644 (9)0.0213 (3)
H14C0.96990.82450.63100.026*
C15C1.06656 (14)0.67620 (13)0.64655 (8)0.0189 (3)
H15C1.12540.68160.63130.023*
C16C0.77946 (16)0.85010 (14)0.66691 (10)0.0273 (4)
H16E0.79480.90470.66720.033*
H16F0.74690.83920.70680.033*
C17C0.69856 (16)0.88136 (15)0.60530 (10)0.0282 (4)
H17C0.68710.82430.60350.034*
C18C0.7398 (2)0.91101 (18)0.54091 (11)0.0405 (5)
H18G0.68900.92820.50380.061*
H18H0.80600.85600.53670.061*
H18I0.75040.96750.54170.061*
C19C0.59313 (18)0.96733 (17)0.61220 (12)0.0396 (5)
H19G0.54270.98460.57480.059*
H19H0.60291.02410.61370.059*
H19I0.56720.94760.65250.059*
C20C1.10908 (14)0.36409 (13)0.47611 (8)0.0187 (3)
H20D1.18390.33990.47390.028*
H20E1.07110.43200.45040.028*
H20F1.08650.32340.45860.028*
C21C1.26744 (14)0.47668 (14)0.71559 (9)0.0240 (4)
H21G1.33150.41860.71270.036*
H21H1.25050.46960.76060.036*
H21I1.27740.53490.70230.036*
Cl1D0.33409 (4)0.15331 (4)0.67365 (3)0.03099 (11)
O1D0.76092 (10)0.52467 (10)0.57158 (6)0.0216 (2)
N1D0.60890 (11)0.39985 (10)0.58141 (7)0.0167 (3)
N2D0.66647 (11)0.44725 (11)0.55537 (7)0.0162 (3)
C1D0.52222 (15)0.28151 (14)0.64529 (8)0.0222 (3)
H1DA0.56280.29650.67160.027*
C2D0.46518 (15)0.23513 (14)0.67528 (9)0.0243 (4)
H2DA0.46700.21940.72130.029*
C3D0.40526 (13)0.21239 (13)0.63595 (9)0.0212 (3)
C4D0.40132 (14)0.23549 (13)0.56744 (9)0.0221 (3)
H4DA0.36050.22030.54150.026*
C5D0.45956 (14)0.28198 (13)0.53786 (8)0.0198 (3)
H5DA0.45790.29700.49180.024*
C6D0.51998 (13)0.30627 (12)0.57588 (8)0.0162 (3)
C7D0.58123 (13)0.35672 (12)0.54432 (8)0.0157 (3)
C8D0.70674 (13)0.48495 (12)0.59466 (8)0.0156 (3)
C9D0.68056 (13)0.47965 (12)0.66623 (8)0.0155 (3)
H9DA0.66240.42530.68060.019*
C10D0.58518 (13)0.57785 (12)0.66919 (7)0.0152 (3)
C11D0.49736 (14)0.57821 (13)0.69842 (8)0.0191 (3)
H11D0.49620.51820.71540.023*
C12D0.41070 (14)0.66837 (13)0.70236 (9)0.0221 (3)
H12D0.35320.66740.72290.027*
C13D0.40926 (14)0.75970 (13)0.67600 (8)0.0207 (3)
C14D0.49810 (14)0.75835 (13)0.64741 (8)0.0200 (3)
H14D0.49910.81830.62990.024*
C15D0.58506 (14)0.66909 (12)0.64464 (8)0.0178 (3)
H15D0.64410.67000.62620.021*
C16D0.31442 (15)0.85847 (14)0.67582 (9)0.0249 (4)
H16G0.33920.90510.68200.030*
H16H0.27640.84890.71320.030*
C17D0.23748 (15)0.90435 (14)0.61163 (10)0.0257 (4)
H17D0.27820.90560.57370.031*
C18D0.15588 (19)1.01160 (16)0.61008 (12)0.0377 (5)
H18J0.11151.04150.56830.056*
H18K0.19191.04930.61530.056*
H18L0.11301.01150.64570.056*
C19D0.18252 (18)0.84273 (18)0.60520 (13)0.0386 (5)
H19J0.14060.86900.56270.058*
H19K0.13730.84560.63980.058*
H19L0.23480.77460.60910.058*
C20D0.60643 (14)0.35489 (14)0.47427 (8)0.0198 (3)
H20G0.67860.34230.47140.030*
H20H0.55950.41820.44490.030*
H20I0.59730.30300.46170.030*
C21D0.77743 (14)0.45816 (14)0.71156 (9)0.0224 (3)
H21J0.83640.39640.70830.034*
H21K0.76130.45320.75670.034*
H21L0.79540.51140.69810.034*
H2NA0.1426 (18)1.0402 (17)0.9845 (6)0.026 (6)*
H2NB0.6339 (18)1.0537 (17)0.9789 (7)0.029 (6)*
H2NC1.1837 (19)0.4558 (17)0.5201 (6)0.030 (6)*
H2ND0.6834 (19)0.4520 (18)0.5157 (6)0.033 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl1A0.0224 (2)0.0330 (2)0.0319 (2)0.01439 (19)0.00772 (17)0.00239 (19)
O1A0.0165 (6)0.0284 (6)0.0192 (6)0.0084 (5)0.0015 (4)0.0086 (5)
N1A0.0159 (6)0.0157 (6)0.0155 (6)0.0069 (5)0.0012 (5)0.0037 (5)
N2A0.0169 (6)0.0178 (6)0.0129 (6)0.0074 (5)0.0014 (5)0.0057 (5)
C1A0.0215 (8)0.0206 (8)0.0150 (7)0.0094 (6)0.0018 (6)0.0034 (6)
C2A0.0256 (9)0.0204 (8)0.0165 (7)0.0120 (7)0.0014 (6)0.0017 (6)
C3A0.0195 (8)0.0176 (7)0.0223 (8)0.0101 (6)0.0040 (6)0.0000 (6)
C4A0.0189 (8)0.0206 (8)0.0217 (8)0.0106 (6)0.0027 (6)0.0036 (6)
C5A0.0193 (8)0.0172 (7)0.0150 (7)0.0083 (6)0.0023 (6)0.0023 (6)
C6A0.0178 (7)0.0138 (6)0.0141 (7)0.0076 (6)0.0016 (5)0.0036 (5)
C7A0.0184 (7)0.0138 (6)0.0137 (7)0.0076 (6)0.0018 (5)0.0032 (5)
C8A0.0182 (7)0.0159 (7)0.0151 (7)0.0086 (6)0.0029 (5)0.0047 (5)
C9A0.0190 (7)0.0176 (7)0.0117 (6)0.0085 (6)0.0032 (5)0.0039 (5)
C10A0.0191 (7)0.0183 (7)0.0108 (6)0.0086 (6)0.0033 (5)0.0051 (5)
C11A0.0220 (8)0.0214 (8)0.0165 (7)0.0097 (7)0.0021 (6)0.0026 (6)
C12A0.0286 (9)0.0262 (9)0.0181 (8)0.0143 (7)0.0035 (7)0.0050 (7)
C13A0.0330 (10)0.0227 (8)0.0152 (7)0.0140 (7)0.0036 (6)0.0077 (6)
C14A0.0271 (9)0.0172 (7)0.0185 (8)0.0069 (7)0.0047 (6)0.0059 (6)
C15A0.0177 (8)0.0195 (7)0.0162 (7)0.0069 (6)0.0031 (6)0.0047 (6)
C16A0.0422 (12)0.0266 (9)0.0231 (9)0.0187 (9)0.0028 (8)0.0111 (7)
C17A0.0372 (11)0.0239 (9)0.0254 (9)0.0172 (8)0.0003 (8)0.0049 (7)
C18A0.0523 (15)0.0344 (11)0.0288 (10)0.0220 (11)0.0033 (10)0.0019 (9)
C19A0.0495 (14)0.0346 (11)0.0420 (13)0.0270 (11)0.0042 (10)0.0093 (10)
C2OA0.0191 (8)0.0220 (8)0.0144 (7)0.0093 (6)0.0027 (6)0.0069 (6)
C21A0.0290 (9)0.0260 (9)0.0189 (8)0.0165 (7)0.0088 (7)0.0070 (7)
Cl1B0.0221 (2)0.0328 (2)0.0368 (3)0.01450 (19)0.01090 (18)0.0050 (2)
O1B0.0185 (6)0.0274 (6)0.0190 (6)0.0103 (5)0.0027 (4)0.0091 (5)
N1B0.0169 (6)0.0181 (6)0.0155 (6)0.0085 (5)0.0019 (5)0.0050 (5)
N2B0.0159 (6)0.0205 (6)0.0148 (6)0.0084 (5)0.0021 (5)0.0067 (5)
C1B0.0229 (9)0.0263 (8)0.0154 (7)0.0114 (7)0.0017 (6)0.0041 (6)
C2B0.0268 (9)0.0274 (9)0.0167 (8)0.0125 (7)0.0046 (6)0.0013 (7)
C3B0.0202 (8)0.0179 (7)0.0255 (8)0.0107 (6)0.0048 (6)0.0003 (6)
C4B0.0182 (8)0.0243 (8)0.0228 (8)0.0107 (7)0.0015 (6)0.0006 (7)
C5B0.0201 (8)0.0235 (8)0.0161 (7)0.0107 (7)0.0014 (6)0.0019 (6)
C6B0.0178 (7)0.0165 (7)0.0143 (7)0.0083 (6)0.0007 (5)0.0041 (5)
C7B0.0181 (7)0.0178 (7)0.0134 (7)0.0100 (6)0.0021 (5)0.0041 (5)
C8B0.0187 (7)0.0159 (7)0.0151 (7)0.0094 (6)0.0036 (5)0.0052 (5)
C9B0.0199 (8)0.0164 (7)0.0136 (7)0.0093 (6)0.0032 (5)0.0043 (5)
C10B0.0190 (7)0.0168 (7)0.0114 (6)0.0088 (6)0.0032 (5)0.0044 (5)
C11B0.0207 (8)0.0163 (7)0.0157 (7)0.0074 (6)0.0014 (6)0.0027 (6)
C12B0.0258 (9)0.0216 (8)0.0193 (8)0.0125 (7)0.0034 (6)0.0053 (6)
C13B0.0297 (9)0.0174 (7)0.0149 (7)0.0118 (7)0.0023 (6)0.0060 (6)
C14B0.0216 (8)0.0177 (7)0.0186 (7)0.0052 (6)0.0028 (6)0.0052 (6)
C15B0.0187 (8)0.0199 (7)0.0159 (7)0.0080 (6)0.0032 (6)0.0049 (6)
C16B0.0360 (10)0.0186 (8)0.0206 (8)0.0129 (7)0.0020 (7)0.0081 (6)
C17B0.0332 (10)0.0222 (8)0.0235 (8)0.0147 (8)0.0032 (7)0.0076 (7)
C18B0.0405 (13)0.0385 (12)0.0514 (14)0.0256 (10)0.0184 (11)0.0202 (11)
C19B0.0533 (14)0.0237 (9)0.0374 (12)0.0202 (10)0.0067 (10)0.0079 (9)
C20B0.0201 (8)0.0280 (9)0.0152 (7)0.0112 (7)0.0027 (6)0.0083 (6)
C21B0.0309 (10)0.0268 (9)0.0192 (8)0.0188 (8)0.0100 (7)0.0071 (7)
Cl1C0.0259 (2)0.0361 (3)0.0350 (3)0.0180 (2)0.00643 (19)0.0037 (2)
O1C0.0241 (6)0.0286 (6)0.0199 (6)0.0161 (5)0.0070 (5)0.0104 (5)
N1C0.0168 (6)0.0166 (6)0.0154 (6)0.0076 (5)0.0022 (5)0.0039 (5)
N2C0.0193 (7)0.0197 (6)0.0139 (6)0.0101 (5)0.0043 (5)0.0065 (5)
C1C0.0196 (8)0.0208 (8)0.0145 (7)0.0083 (6)0.0014 (6)0.0033 (6)
C2C0.0207 (8)0.0216 (8)0.0162 (7)0.0072 (7)0.0034 (6)0.0005 (6)
C3C0.0169 (8)0.0187 (7)0.0234 (8)0.0077 (6)0.0047 (6)0.0001 (6)
C4C0.0180 (8)0.0217 (8)0.0225 (8)0.0096 (7)0.0000 (6)0.0020 (6)
C5C0.0202 (8)0.0180 (7)0.0148 (7)0.0085 (6)0.0006 (6)0.0015 (6)
C6C0.0147 (7)0.0143 (7)0.0152 (7)0.0046 (6)0.0023 (5)0.0029 (5)
C7C0.0155 (7)0.0148 (7)0.0138 (7)0.0050 (6)0.0014 (5)0.0032 (5)
C8C0.0149 (7)0.0166 (7)0.0155 (7)0.0053 (6)0.0010 (5)0.0049 (6)
C9C0.0190 (8)0.0174 (7)0.0127 (6)0.0074 (6)0.0010 (5)0.0050 (5)
C10C0.0184 (7)0.0165 (7)0.0112 (6)0.0080 (6)0.0012 (5)0.0034 (5)
C11C0.0207 (8)0.0197 (7)0.0163 (7)0.0098 (6)0.0039 (6)0.0034 (6)
C12C0.0210 (8)0.0250 (8)0.0175 (7)0.0098 (7)0.0066 (6)0.0047 (6)
C13C0.0234 (8)0.0211 (8)0.0147 (7)0.0066 (7)0.0045 (6)0.0065 (6)
C14C0.0277 (9)0.0175 (7)0.0188 (8)0.0105 (7)0.0039 (6)0.0047 (6)
C15C0.0224 (8)0.0201 (7)0.0173 (7)0.0119 (7)0.0039 (6)0.0060 (6)
C16C0.0267 (10)0.0237 (9)0.0236 (9)0.0040 (7)0.0066 (7)0.0086 (7)
C17C0.0270 (10)0.0227 (9)0.0251 (9)0.0053 (7)0.0040 (7)0.0018 (7)
C18C0.0451 (14)0.0347 (11)0.0272 (10)0.0100 (10)0.0062 (9)0.0003 (9)
C19C0.0311 (12)0.0335 (11)0.0411 (12)0.0056 (9)0.0029 (9)0.0063 (9)
C20C0.0221 (8)0.0224 (8)0.0155 (7)0.0129 (7)0.0043 (6)0.0063 (6)
C21C0.0206 (8)0.0273 (9)0.0195 (8)0.0062 (7)0.0026 (6)0.0084 (7)
Cl1D0.0232 (2)0.0314 (2)0.0346 (2)0.01496 (19)0.00650 (18)0.00417 (19)
O1D0.0254 (6)0.0279 (6)0.0191 (6)0.0172 (5)0.0069 (5)0.0096 (5)
N1D0.0170 (6)0.0181 (6)0.0153 (6)0.0080 (5)0.0026 (5)0.0052 (5)
N2D0.0184 (7)0.0202 (6)0.0134 (6)0.0107 (5)0.0040 (5)0.0067 (5)
C1D0.0257 (9)0.0273 (9)0.0146 (7)0.0135 (7)0.0026 (6)0.0045 (6)
C2D0.0258 (9)0.0261 (9)0.0180 (8)0.0112 (7)0.0058 (7)0.0022 (7)
C3D0.0148 (7)0.0183 (7)0.0246 (8)0.0053 (6)0.0046 (6)0.0004 (6)
C4D0.0192 (8)0.0238 (8)0.0226 (8)0.0116 (7)0.0009 (6)0.0014 (7)
C5D0.0206 (8)0.0226 (8)0.0165 (7)0.0116 (7)0.0008 (6)0.0021 (6)
C6D0.0165 (7)0.0162 (7)0.0151 (7)0.0066 (6)0.0024 (5)0.0046 (6)
C7D0.0153 (7)0.0168 (7)0.0140 (7)0.0066 (6)0.0015 (5)0.0042 (5)
C8D0.0156 (7)0.0157 (7)0.0149 (7)0.0058 (6)0.0014 (5)0.0060 (5)
C9D0.0164 (7)0.0162 (7)0.0130 (6)0.0065 (6)0.0012 (5)0.0045 (5)
C10D0.0172 (7)0.0164 (7)0.0109 (6)0.0066 (6)0.0010 (5)0.0044 (5)
C11D0.0205 (8)0.0199 (7)0.0159 (7)0.0096 (6)0.0033 (6)0.0024 (6)
C12D0.0204 (8)0.0242 (8)0.0190 (8)0.0082 (7)0.0077 (6)0.0050 (6)
C13D0.0218 (8)0.0197 (8)0.0159 (7)0.0048 (6)0.0026 (6)0.0070 (6)
C14D0.0261 (9)0.0157 (7)0.0174 (7)0.0088 (6)0.0011 (6)0.0047 (6)
C15D0.0201 (8)0.0189 (7)0.0159 (7)0.0104 (6)0.0020 (6)0.0047 (6)
C16D0.0274 (9)0.0210 (8)0.0220 (8)0.0059 (7)0.0053 (7)0.0098 (7)
C17D0.0229 (9)0.0219 (8)0.0251 (9)0.0039 (7)0.0031 (7)0.0074 (7)
C18D0.0357 (12)0.0257 (10)0.0373 (12)0.0025 (9)0.0004 (9)0.0080 (9)
C19D0.0267 (11)0.0384 (12)0.0524 (14)0.0125 (9)0.0043 (10)0.0209 (11)
C20D0.0210 (8)0.0281 (8)0.0150 (7)0.0139 (7)0.0041 (6)0.0090 (6)
C21D0.0181 (8)0.0246 (8)0.0205 (8)0.0051 (7)0.0027 (6)0.0092 (7)
Geometric parameters (Å, º) top
Cl1A—C3A1.7411 (18)Cl1C—C3C1.7396 (17)
O1A—C8A1.230 (2)O1C—C8C1.234 (2)
N1A—C7A1.288 (2)N1C—C7C1.290 (2)
N1A—N2A1.3720 (19)N1C—N2C1.3766 (19)
N2A—C8A1.358 (2)N2C—C8C1.361 (2)
N2A—H2NA0.846 (9)N2C—H2NC0.845 (9)
C1A—C2A1.383 (2)C1C—C2C1.389 (2)
C1A—C6A1.399 (2)C1C—C6C1.400 (2)
C1A—H1AA0.9300C1C—H1CA0.9300
C2A—C3A1.391 (3)C2C—C3C1.386 (3)
C2A—H2AA0.9300C2C—H2CA0.9300
C3A—C4A1.382 (2)C3C—C4C1.384 (2)
C4A—C5A1.390 (2)C4C—C5C1.393 (2)
C4A—H4AA0.9300C4C—H4CA0.9300
C5A—C6A1.399 (2)C5C—C6C1.398 (2)
C5A—H5AA0.9300C5C—H5CA0.9300
C6A—C7A1.487 (2)C6C—C7C1.485 (2)
C7A—C2OA1.506 (2)C7C—C20C1.502 (2)
C8A—C9A1.525 (2)C8C—C9C1.520 (2)
C9A—C10A1.526 (2)C9C—C10C1.523 (2)
C9A—C21A1.531 (2)C9C—C21C1.534 (2)
C9A—H9AA0.9800C9C—H9CA0.9800
C10A—C11A1.396 (2)C10C—C15C1.396 (2)
C10A—C15A1.398 (2)C10C—C11C1.399 (2)
C11A—C12A1.397 (2)C11C—C12C1.388 (2)
C11A—H11A0.9300C11C—H11C0.9300
C12A—C13A1.390 (3)C12C—C13C1.395 (2)
C12A—H12A0.9300C12C—H12C0.9300
C13A—C14A1.403 (3)C13C—C14C1.402 (3)
C13A—C16A1.513 (3)C13C—C16C1.508 (2)
C14A—C15A1.390 (2)C14C—C15C1.392 (2)
C14A—H14A0.9300C14C—H14C0.9300
C15A—H15A0.9300C15C—H15C0.9300
C16A—C17A1.543 (3)C16C—C17C1.554 (3)
C16A—H16A0.9700C16C—H16E0.9700
C16A—H16B0.9700C16C—H16F0.9700
C17A—C18A1.526 (3)C17C—C19C1.519 (3)
C17A—C19A1.530 (3)C17C—C18C1.525 (3)
C17A—H17A0.9800C17C—H17C0.9800
C18A—H18A0.9600C18C—H18G0.9600
C18A—H18B0.9600C18C—H18H0.9600
C18A—H18C0.9600C18C—H18I0.9600
C19A—H19A0.9600C19C—H19G0.9600
C19A—H19B0.9600C19C—H19H0.9600
C19A—H19C0.9600C19C—H19I0.9600
C2OA—H2OA0.9600C20C—H20D0.9600
C2OA—H2OB0.9600C20C—H20E0.9600
C2OA—H2OC0.9600C20C—H20F0.9600
C21A—H21A0.9600C21C—H21G0.9600
C21A—H21B0.9600C21C—H21H0.9600
C21A—H21C0.9600C21C—H21I0.9600
Cl1B—C3B1.7383 (18)Cl1D—C3D1.7403 (18)
O1B—C8B1.230 (2)O1D—C8D1.232 (2)
N1B—C7B1.290 (2)N1D—C7D1.290 (2)
N1B—N2B1.379 (2)N1D—N2D1.3752 (19)
N2B—C8B1.361 (2)N2D—C8D1.361 (2)
N2B—H2NB0.853 (9)N2D—H2ND0.855 (9)
C1B—C2B1.383 (3)C1D—C2D1.383 (2)
C1B—C6B1.406 (2)C1D—C6D1.403 (2)
C1B—H1BA0.9300C1D—H1DA0.9300
C2B—C3B1.384 (3)C2D—C3D1.386 (3)
C2B—H2BA0.9300C2D—H2DA0.9300
C3B—C4B1.385 (3)C3D—C4D1.382 (2)
C4B—C5B1.391 (2)C4D—C5D1.395 (2)
C4B—H4BA0.9300C4D—H4DA0.9300
C5B—C6B1.394 (2)C5D—C6D1.391 (2)
C5B—H5BA0.9300C5D—H5DA0.9300
C6B—C7B1.481 (2)C6D—C7D1.487 (2)
C7B—C20B1.503 (2)C7D—C20D1.501 (2)
C8B—C9B1.525 (2)C8D—C9D1.525 (2)
C9B—C10B1.521 (2)C9D—C10D1.523 (2)
C9B—C21B1.538 (2)C9D—C21D1.531 (2)
C9B—H9BA0.9800C9D—H9DA0.9800
C10B—C11B1.392 (2)C10D—C11D1.391 (2)
C10B—C15B1.396 (2)C10D—C15D1.397 (2)
C11B—C12B1.396 (2)C11D—C12D1.400 (2)
C11B—H11B0.9300C11D—H11D0.9300
C12B—C13B1.395 (2)C12D—C13D1.395 (3)
C12B—H12B0.9300C12D—H12D0.9300
C13B—C14B1.395 (3)C13D—C14D1.393 (3)
C13B—C16B1.508 (2)C13D—C16D1.510 (2)
C14B—C15B1.391 (2)C14D—C15D1.387 (2)
C14B—H14B0.9300C14D—H14D0.9300
C15B—H15B0.9300C15D—H15D0.9300
C16B—C17B1.530 (3)C16D—C17D1.534 (3)
C16B—H16C0.9700C16D—H16G0.9700
C16B—H16D0.9700C16D—H16H0.9700
C17B—C18B1.517 (3)C17D—C19D1.514 (3)
C17B—C19B1.528 (3)C17D—C18D1.527 (3)
C17B—H17B0.9800C17D—H17D0.9800
C18B—H18D0.9600C18D—H18J0.9600
C18B—H18E0.9600C18D—H18K0.9600
C18B—H18F0.9600C18D—H18L0.9600
C19B—H19D0.9600C19D—H19J0.9600
C19B—H19E0.9600C19D—H19K0.9600
C19B—H19F0.9600C19D—H19L0.9600
C20B—H20A0.9600C20D—H20G0.9600
C20B—H20B0.9600C20D—H20H0.9600
C20B—H20C0.9600C20D—H20I0.9600
C21B—H21D0.9600C21D—H21J0.9600
C21B—H21E0.9600C21D—H21K0.9600
C21B—H21F0.9600C21D—H21L0.9600
C7A—N1A—N2A117.79 (14)C7C—N1C—N2C117.50 (13)
C8A—N2A—N1A120.07 (13)C8C—N2C—N1C120.35 (13)
C8A—N2A—H2NA116.6 (16)C8C—N2C—H2NC118.2 (16)
N1A—N2A—H2NA123.3 (16)N1C—N2C—H2NC121.5 (16)
C2A—C1A—C6A121.00 (16)C2C—C1C—C6C120.73 (16)
C2A—C1A—H1AA119.5C2C—C1C—H1CA119.6
C6A—C1A—H1AA119.5C6C—C1C—H1CA119.6
C1A—C2A—C3A119.23 (16)C3C—C2C—C1C119.57 (16)
C1A—C2A—H2AA120.4C3C—C2C—H2CA120.2
C3A—C2A—H2AA120.4C1C—C2C—H2CA120.2
C4A—C3A—C2A121.09 (16)C4C—C3C—C2C120.95 (16)
C4A—C3A—Cl1A119.70 (14)C4C—C3C—Cl1C119.61 (14)
C2A—C3A—Cl1A119.21 (13)C2C—C3C—Cl1C119.43 (13)
C3A—C4A—C5A119.27 (16)C3C—C4C—C5C119.29 (17)
C3A—C4A—H4AA120.4C3C—C4C—H4CA120.4
C5A—C4A—H4AA120.4C5C—C4C—H4CA120.4
C4A—C5A—C6A120.87 (15)C4C—C5C—C6C120.86 (15)
C4A—C5A—H5AA119.6C4C—C5C—H5CA119.6
C6A—C5A—H5AA119.6C6C—C5C—H5CA119.6
C5A—C6A—C1A118.54 (15)C5C—C6C—C1C118.59 (15)
C5A—C6A—C7A121.23 (14)C5C—C6C—C7C121.12 (14)
C1A—C6A—C7A120.22 (14)C1C—C6C—C7C120.28 (15)
N1A—C7A—C6A115.10 (14)N1C—C7C—C6C115.22 (14)
N1A—C7A—C2OA124.00 (15)N1C—C7C—C20C124.27 (15)
C6A—C7A—C2OA120.90 (14)C6C—C7C—C20C120.50 (14)
O1A—C8A—N2A119.99 (15)O1C—C8C—N2C119.73 (15)
O1A—C8A—C9A121.55 (14)O1C—C8C—C9C121.88 (15)
N2A—C8A—C9A118.44 (14)N2C—C8C—C9C118.36 (14)
C8A—C9A—C10A108.95 (13)C8C—C9C—C10C108.80 (13)
C8A—C9A—C21A109.38 (14)C8C—C9C—C21C109.77 (14)
C10A—C9A—C21A112.13 (13)C10C—C9C—C21C111.96 (13)
C8A—C9A—H9AA108.8C8C—C9C—H9CA108.8
C10A—C9A—H9AA108.8C10C—C9C—H9CA108.8
C21A—C9A—H9AA108.8C21C—C9C—H9CA108.8
C11A—C10A—C15A118.27 (15)C15C—C10C—C11C118.21 (15)
C11A—C10A—C9A120.98 (15)C15C—C10C—C9C120.54 (15)
C15A—C10A—C9A120.75 (15)C11C—C10C—C9C121.25 (14)
C10A—C11A—C12A120.76 (16)C12C—C11C—C10C120.78 (16)
C10A—C11A—H11A119.6C12C—C11C—H11C119.6
C12A—C11A—H11A119.6C10C—C11C—H11C119.6
C13A—C12A—C11A121.30 (17)C11C—C12C—C13C121.50 (16)
C13A—C12A—H12A119.4C11C—C12C—H12C119.2
C11A—C12A—H12A119.4C13C—C12C—H12C119.2
C12A—C13A—C14A117.62 (16)C12C—C13C—C14C117.50 (16)
C12A—C13A—C16A120.80 (18)C12C—C13C—C16C120.90 (17)
C14A—C13A—C16A121.57 (17)C14C—C13C—C16C121.58 (17)
C15A—C14A—C13A121.42 (17)C15C—C14C—C13C121.25 (16)
C15A—C14A—H14A119.3C15C—C14C—H14C119.4
C13A—C14A—H14A119.3C13C—C14C—H14C119.4
C14A—C15A—C10A120.61 (16)C14C—C15C—C10C120.75 (16)
C14A—C15A—H15A119.7C14C—C15C—H15C119.6
C10A—C15A—H15A119.7C10C—C15C—H15C119.6
C13A—C16A—C17A114.33 (15)C13C—C16C—C17C114.18 (15)
C13A—C16A—H16A108.7C13C—C16C—H16E108.7
C17A—C16A—H16A108.7C17C—C16C—H16E108.7
C13A—C16A—H16B108.7C13C—C16C—H16F108.7
C17A—C16A—H16B108.7C17C—C16C—H16F108.7
H16A—C16A—H16B107.6H16E—C16C—H16F107.6
C18A—C17A—C19A109.84 (18)C19C—C17C—C18C110.07 (18)
C18A—C17A—C16A112.05 (18)C19C—C17C—C16C109.86 (17)
C19A—C17A—C16A109.77 (17)C18C—C17C—C16C111.50 (18)
C18A—C17A—H17A108.4C19C—C17C—H17C108.4
C19A—C17A—H17A108.4C18C—C17C—H17C108.4
C16A—C17A—H17A108.4C16C—C17C—H17C108.4
C17A—C18A—H18A109.5C17C—C18C—H18G109.5
C17A—C18A—H18B109.5C17C—C18C—H18H109.5
H18A—C18A—H18B109.5H18G—C18C—H18H109.5
C17A—C18A—H18C109.5C17C—C18C—H18I109.5
H18A—C18A—H18C109.5H18G—C18C—H18I109.5
H18B—C18A—H18C109.5H18H—C18C—H18I109.5
C17A—C19A—H19A109.5C17C—C19C—H19G109.5
C17A—C19A—H19B109.5C17C—C19C—H19H109.5
H19A—C19A—H19B109.5H19G—C19C—H19H109.5
C17A—C19A—H19C109.5C17C—C19C—H19I109.5
H19A—C19A—H19C109.5H19G—C19C—H19I109.5
H19B—C19A—H19C109.5H19H—C19C—H19I109.5
C7A—C2OA—H2OA109.5C7C—C20C—H20D109.5
C7A—C2OA—H2OB109.5C7C—C20C—H20E109.5
H2OA—C2OA—H2OB109.5H20D—C20C—H20E109.5
C7A—C2OA—H2OC109.5C7C—C20C—H20F109.5
H2OA—C2OA—H2OC109.5H20D—C20C—H20F109.5
H2OB—C2OA—H2OC109.5H20E—C20C—H20F109.5
C9A—C21A—H21A109.5C9C—C21C—H21G109.5
C9A—C21A—H21B109.5C9C—C21C—H21H109.5
H21A—C21A—H21B109.5H21G—C21C—H21H109.5
C9A—C21A—H21C109.5C9C—C21C—H21I109.5
H21A—C21A—H21C109.5H21G—C21C—H21I109.5
H21B—C21A—H21C109.5H21H—C21C—H21I109.5
C7B—N1B—N2B117.65 (14)C7D—N1D—N2D117.98 (13)
C8B—N2B—N1B120.33 (14)C8D—N2D—N1D120.11 (13)
C8B—N2B—H2NB115.2 (16)C8D—N2D—H2ND115.2 (17)
N1B—N2B—H2NB124.0 (16)N1D—N2D—H2ND124.5 (17)
C2B—C1B—C6B121.02 (16)C2D—C1D—C6D121.11 (17)
C2B—C1B—H1BA119.5C2D—C1D—H1DA119.4
C6B—C1B—H1BA119.5C6D—C1D—H1DA119.4
C1B—C2B—C3B119.42 (16)C1D—C2D—C3D119.26 (16)
C1B—C2B—H2BA120.3C1D—C2D—H2DA120.4
C3B—C2B—H2BA120.3C3D—C2D—H2DA120.4
C2B—C3B—C4B121.10 (16)C4D—C3D—C2D121.22 (16)
C2B—C3B—Cl1B119.45 (14)C4D—C3D—Cl1D119.47 (15)
C4B—C3B—Cl1B119.45 (14)C2D—C3D—Cl1D119.31 (14)
C3B—C4B—C5B119.09 (17)C3D—C4D—C5D118.91 (17)
C3B—C4B—H4BA120.5C3D—C4D—H4DA120.5
C5B—C4B—H4BA120.5C5D—C4D—H4DA120.5
C4B—C5B—C6B121.24 (16)C6D—C5D—C4D121.28 (16)
C4B—C5B—H5BA119.4C6D—C5D—H5DA119.4
C6B—C5B—H5BA119.4C4D—C5D—H5DA119.4
C5B—C6B—C1B118.13 (16)C5D—C6D—C1D118.21 (15)
C5B—C6B—C7B121.43 (14)C5D—C6D—C7D121.30 (14)
C1B—C6B—C7B120.44 (15)C1D—C6D—C7D120.49 (15)
N1B—C7B—C6B115.27 (14)N1D—C7D—C6D115.06 (14)
N1B—C7B—C20B124.72 (15)N1D—C7D—C20D124.86 (15)
C6B—C7B—C20B120.01 (14)C6D—C7D—C20D120.08 (14)
O1B—C8B—N2B119.82 (15)O1D—C8D—N2D119.81 (14)
O1B—C8B—C9B121.44 (14)O1D—C8D—C9D121.39 (14)
N2B—C8B—C9B118.70 (14)N2D—C8D—C9D118.77 (14)
C10B—C9B—C8B108.88 (13)C10D—C9D—C8D109.06 (13)
C10B—C9B—C21B111.48 (13)C10D—C9D—C21D111.33 (13)
C8B—C9B—C21B109.86 (14)C8D—C9D—C21D109.66 (14)
C10B—C9B—H9BA108.9C10D—C9D—H9DA108.9
C8B—C9B—H9BA108.9C8D—C9D—H9DA108.9
C21B—C9B—H9BA108.9C21D—C9D—H9DA108.9
C11B—C10B—C15B118.49 (15)C11D—C10D—C15D118.49 (15)
C11B—C10B—C9B120.60 (15)C11D—C10D—C9D120.46 (14)
C15B—C10B—C9B120.88 (15)C15D—C10D—C9D121.02 (14)
C10B—C11B—C12B120.59 (16)C10D—C11D—C12D120.40 (16)
C10B—C11B—H11B119.7C10D—C11D—H11D119.8
C12B—C11B—H11B119.7C12D—C11D—H11D119.8
C13B—C12B—C11B121.11 (16)C13D—C12D—C11D121.07 (16)
C13B—C12B—H12B119.4C13D—C12D—H12D119.5
C11B—C12B—H12B119.4C11D—C12D—H12D119.5
C12B—C13B—C14B117.95 (15)C14D—C13D—C12D118.00 (16)
C12B—C13B—C16B122.14 (17)C14D—C13D—C16D119.62 (16)
C14B—C13B—C16B119.90 (16)C12D—C13D—C16D122.35 (17)
C15B—C14B—C13B121.14 (16)C15D—C14D—C13D121.12 (16)
C15B—C14B—H14B119.4C15D—C14D—H14D119.4
C13B—C14B—H14B119.4C13D—C14D—H14D119.4
C14B—C15B—C10B120.70 (16)C14D—C15D—C10D120.87 (16)
C14B—C15B—H15B119.6C14D—C15D—H15D119.6
C10B—C15B—H15B119.6C10D—C15D—H15D119.6
C13B—C16B—C17B113.53 (14)C13D—C16D—C17D113.48 (15)
C13B—C16B—H16C108.9C13D—C16D—H16G108.9
C17B—C16B—H16C108.9C17D—C16D—H16G108.9
C13B—C16B—H16D108.9C13D—C16D—H16H108.9
C17B—C16B—H16D108.9C17D—C16D—H16H108.9
H16C—C16B—H16D107.7H16G—C16D—H16H107.7
C18B—C17B—C19B110.00 (18)C19D—C17D—C18D110.44 (18)
C18B—C17B—C16B111.07 (17)C19D—C17D—C16D111.14 (17)
C19B—C17B—C16B110.41 (16)C18D—C17D—C16D109.97 (16)
C18B—C17B—H17B108.4C19D—C17D—H17D108.4
C19B—C17B—H17B108.4C18D—C17D—H17D108.4
C16B—C17B—H17B108.4C16D—C17D—H17D108.4
C17B—C18B—H18D109.5C17D—C18D—H18J109.5
C17B—C18B—H18E109.5C17D—C18D—H18K109.5
H18D—C18B—H18E109.5H18J—C18D—H18K109.5
C17B—C18B—H18F109.5C17D—C18D—H18L109.5
H18D—C18B—H18F109.5H18J—C18D—H18L109.5
H18E—C18B—H18F109.5H18K—C18D—H18L109.5
C17B—C19B—H19D109.5C17D—C19D—H19J109.5
C17B—C19B—H19E109.5C17D—C19D—H19K109.5
H19D—C19B—H19E109.5H19J—C19D—H19K109.5
C17B—C19B—H19F109.5C17D—C19D—H19L109.5
H19D—C19B—H19F109.5H19J—C19D—H19L109.5
H19E—C19B—H19F109.5H19K—C19D—H19L109.5
C7B—C20B—H20A109.5C7D—C20D—H20G109.5
C7B—C20B—H20B109.5C7D—C20D—H20H109.5
H20A—C20B—H20B109.5H20G—C20D—H20H109.5
C7B—C20B—H20C109.5C7D—C20D—H20I109.5
H20A—C20B—H20C109.5H20G—C20D—H20I109.5
H20B—C20B—H20C109.5H20H—C20D—H20I109.5
C9B—C21B—H21D109.5C9D—C21D—H21J109.5
C9B—C21B—H21E109.5C9D—C21D—H21K109.5
H21D—C21B—H21E109.5H21J—C21D—H21K109.5
C9B—C21B—H21F109.5C9D—C21D—H21L109.5
H21D—C21B—H21F109.5H21J—C21D—H21L109.5
H21E—C21B—H21F109.5H21K—C21D—H21L109.5
C7A—N1A—N2A—C8A177.18 (15)C7C—N1C—N2C—C8C178.36 (15)
C6A—C1A—C2A—C3A0.1 (3)C6C—C1C—C2C—C3C0.1 (3)
C1A—C2A—C3A—C4A0.6 (3)C1C—C2C—C3C—C4C0.6 (3)
C1A—C2A—C3A—Cl1A179.72 (13)C1C—C2C—C3C—Cl1C179.01 (13)
C2A—C3A—C4A—C5A0.3 (3)C2C—C3C—C4C—C5C0.3 (3)
Cl1A—C3A—C4A—C5A179.97 (13)Cl1C—C3C—C4C—C5C179.27 (13)
C3A—C4A—C5A—C6A0.4 (3)C3C—C4C—C5C—C6C0.5 (3)
C4A—C5A—C6A—C1A0.9 (2)C4C—C5C—C6C—C1C0.9 (2)
C4A—C5A—C6A—C7A177.91 (15)C4C—C5C—C6C—C7C177.80 (15)
C2A—C1A—C6A—C5A0.7 (2)C2C—C1C—C6C—C5C0.7 (2)
C2A—C1A—C6A—C7A178.17 (15)C2C—C1C—C6C—C7C178.07 (15)
N2A—N1A—C7A—C6A179.62 (13)N2C—N1C—C7C—C6C179.68 (13)
N2A—N1A—C7A—C2OA0.5 (2)N2C—N1C—C7C—C20C0.1 (2)
C5A—C6A—C7A—N1A158.74 (15)C5C—C6C—C7C—N1C157.33 (15)
C1A—C6A—C7A—N1A20.1 (2)C1C—C6C—C7C—N1C21.4 (2)
C5A—C6A—C7A—C2OA20.4 (2)C5C—C6C—C7C—C20C22.3 (2)
C1A—C6A—C7A—C2OA160.83 (15)C1C—C6C—C7C—C20C159.02 (15)
N1A—N2A—C8A—O1A178.98 (15)N1C—N2C—C8C—O1C177.82 (15)
N1A—N2A—C8A—C9A2.6 (2)N1C—N2C—C8C—C9C4.0 (2)
O1A—C8A—C9A—C10A86.39 (19)O1C—C8C—C9C—C10C86.41 (19)
N2A—C8A—C9A—C10A92.00 (17)N2C—C8C—C9C—C10C91.70 (17)
O1A—C8A—C9A—C21A36.5 (2)O1C—C8C—C9C—C21C36.4 (2)
N2A—C8A—C9A—C21A145.12 (15)N2C—C8C—C9C—C21C145.47 (15)
C8A—C9A—C10A—C11A122.54 (16)C8C—C9C—C10C—C15C58.63 (19)
C21A—C9A—C10A—C11A116.24 (17)C21C—C9C—C10C—C15C62.9 (2)
C8A—C9A—C10A—C15A57.43 (19)C8C—C9C—C10C—C11C121.97 (16)
C21A—C9A—C10A—C15A63.79 (19)C21C—C9C—C10C—C11C116.53 (17)
C15A—C10A—C11A—C12A0.4 (2)C15C—C10C—C11C—C12C0.1 (2)
C9A—C10A—C11A—C12A179.53 (15)C9C—C10C—C11C—C12C179.35 (15)
C10A—C11A—C12A—C13A0.9 (3)C10C—C11C—C12C—C13C0.9 (3)
C11A—C12A—C13A—C14A1.8 (3)C11C—C12C—C13C—C14C1.2 (3)
C11A—C12A—C13A—C16A176.77 (17)C11C—C12C—C13C—C16C177.22 (17)
C12A—C13A—C14A—C15A1.4 (3)C12C—C13C—C14C—C15C0.7 (3)
C16A—C13A—C14A—C15A177.12 (16)C16C—C13C—C14C—C15C177.70 (17)
C13A—C14A—C15A—C10A0.2 (3)C13C—C14C—C15C—C10C0.1 (3)
C11A—C10A—C15A—C14A0.8 (2)C11C—C10C—C15C—C14C0.4 (2)
C9A—C10A—C15A—C14A179.17 (15)C9C—C10C—C15C—C14C179.84 (15)
C12A—C13A—C16A—C17A83.3 (2)C12C—C13C—C16C—C17C81.4 (2)
C14A—C13A—C16A—C17A95.2 (2)C14C—C13C—C16C—C17C96.9 (2)
C13A—C16A—C17A—C18A64.7 (2)C13C—C16C—C17C—C19C172.86 (18)
C13A—C16A—C17A—C19A173.01 (18)C13C—C16C—C17C—C18C64.8 (2)
C7B—N1B—N2B—C8B174.93 (15)C7D—N1D—N2D—C8D173.29 (15)
C6B—C1B—C2B—C3B0.3 (3)C6D—C1D—C2D—C3D0.3 (3)
C1B—C2B—C3B—C4B0.2 (3)C1D—C2D—C3D—C4D0.2 (3)
C1B—C2B—C3B—Cl1B179.83 (14)C1D—C2D—C3D—Cl1D179.60 (14)
C2B—C3B—C4B—C5B0.4 (3)C2D—C3D—C4D—C5D0.4 (3)
Cl1B—C3B—C4B—C5B179.64 (14)Cl1D—C3D—C4D—C5D179.39 (14)
C3B—C4B—C5B—C6B0.0 (3)C3D—C4D—C5D—C6D0.8 (3)
C4B—C5B—C6B—C1B0.5 (3)C4D—C5D—C6D—C1D0.9 (3)
C4B—C5B—C6B—C7B179.38 (16)C4D—C5D—C6D—C7D179.39 (16)
C2B—C1B—C6B—C5B0.7 (3)C2D—C1D—C6D—C5D0.6 (3)
C2B—C1B—C6B—C7B179.19 (16)C2D—C1D—C6D—C7D179.61 (16)
N2B—N1B—C7B—C6B179.48 (13)N2D—N1D—C7D—C6D179.51 (14)
N2B—N1B—C7B—C20B0.1 (2)N2D—N1D—C7D—C20D0.5 (2)
C5B—C6B—C7B—N1B159.53 (16)C5D—C6D—C7D—N1D161.40 (16)
C1B—C6B—C7B—N1B20.3 (2)C1D—C6D—C7D—N1D18.9 (2)
C5B—C6B—C7B—C20B20.8 (2)C5D—C6D—C7D—C20D18.6 (2)
C1B—C6B—C7B—C20B159.34 (16)C1D—C6D—C7D—C20D161.14 (16)
N1B—N2B—C8B—O1B176.82 (15)N1D—N2D—C8D—O1D177.83 (15)
N1B—N2B—C8B—C9B5.5 (2)N1D—N2D—C8D—C9D4.0 (2)
O1B—C8B—C9B—C10B83.14 (19)O1D—C8D—C9D—C10D83.06 (19)
N2B—C8B—C9B—C10B94.54 (17)N2D—C8D—C9D—C10D95.07 (17)
O1B—C8B—C9B—C21B39.2 (2)O1D—C8D—C9D—C21D39.1 (2)
N2B—C8B—C9B—C21B143.12 (15)N2D—C8D—C9D—C21D142.78 (15)
C8B—C9B—C10B—C11B125.80 (16)C8D—C9D—C10D—C11D127.66 (16)
C21B—C9B—C10B—C11B112.85 (17)C21D—C9D—C10D—C11D111.21 (17)
C8B—C9B—C10B—C15B56.36 (19)C8D—C9D—C10D—C15D54.34 (19)
C21B—C9B—C10B—C15B65.00 (19)C21D—C9D—C10D—C15D66.79 (19)
C15B—C10B—C11B—C12B0.0 (2)C15D—C10D—C11D—C12D0.6 (2)
C9B—C10B—C11B—C12B177.93 (15)C9D—C10D—C11D—C12D178.65 (15)
C10B—C11B—C12B—C13B1.4 (3)C10D—C11D—C12D—C13D1.4 (3)
C11B—C12B—C13B—C14B1.5 (3)C11D—C12D—C13D—C14D1.9 (3)
C11B—C12B—C13B—C16B177.09 (16)C11D—C12D—C13D—C16D176.29 (17)
C12B—C13B—C14B—C15B0.2 (3)C12D—C13D—C14D—C15D0.5 (3)
C16B—C13B—C14B—C15B178.42 (16)C16D—C13D—C14D—C15D177.71 (16)
C13B—C14B—C15B—C10B1.2 (3)C13D—C14D—C15D—C10D1.4 (3)
C11B—C10B—C15B—C14B1.3 (2)C11D—C10D—C15D—C14D2.0 (2)
C9B—C10B—C15B—C14B179.21 (15)C9D—C10D—C15D—C14D179.99 (15)
C12B—C13B—C16B—C17B94.0 (2)C14D—C13D—C16D—C17D85.2 (2)
C14B—C13B—C16B—C17B84.6 (2)C12D—C13D—C16D—C17D93.0 (2)
C13B—C16B—C17B—C18B68.2 (2)C13D—C16D—C17D—C19D67.9 (2)
C13B—C16B—C17B—C19B169.45 (18)C13D—C16D—C17D—C18D169.53 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2A—H2NA···O1Bi0.85 (1)2.09 (2)2.9255 (19)169 (3)
N2B—H2NB···O1Ai0.85 (2)2.07 (2)2.916 (2)173 (2)
N2C—H2NC···O1Dii0.85 (2)2.08 (2)2.9085 (19)169 (3)
N2D—H2ND···O1Cii0.86 (2)2.09 (2)2.934 (2)172 (3)
C20B—H20A···O1Ai0.962.473.125 (3)126
C20C—H20D···O1Dii0.962.573.099 (3)115
C20D—H20G···O1Cii0.962.503.175 (3)128
C2OA—H2OC···Cg1iii0.962.753.4628 (19)131
C16C—H16F···Cg20.962.783.744 (2)171
C20B—H20C···Cg2i0.962.943.5787 (19)125
C16A—H16B···Cg3iv0.962.903.860 (2)170
C20C—H20F···Cg3ii0.962.773.4943 (19)132
C16B—H16D···Cg40.962.863.818 (2)171
C20D—H20I···Cg4v0.962.963.5557 (19)122
Symmetry codes: (i) x+1, y+2, z+2; (ii) x+2, y+1, z+1; (iii) x, y+2, z+2; (iv) x1, y, z; (v) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC21H25ClN2O
Mr356.88
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)14.2691 (2), 15.5343 (2), 20.7436 (3)
α, β, γ (°)77.416 (1), 90.058 (1), 62.714 (1)
V3)3961.17 (10)
Z8
Radiation typeMo Kα
µ (mm1)0.20
Crystal size (mm)0.54 × 0.18 × 0.17
Data collection
DiffractometerBruker SMART APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.899, 0.966
No. of measured, independent and
observed [I > 2σ(I)] reflections
132549, 28009, 19617
Rint0.040
(sin θ/λ)max1)0.751
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.065, 0.166, 1.08
No. of reflections28009
No. of parameters933
No. of restraints4
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.65, 0.29

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2A—H2NA···O1Bi0.847 (14)2.090 (17)2.9255 (19)169 (3)
N2B—H2NB···O1Ai0.852 (18)2.069 (18)2.916 (2)173 (2)
N2C—H2NC···O1Dii0.845 (15)2.075 (17)2.9085 (19)169 (3)
N2D—H2ND···O1Cii0.855 (16)2.085 (17)2.934 (2)172 (3)
C20B—H20A···O1Ai0.962.473.125 (3)126
C20C—H20D···O1Dii0.962.573.099 (3)115
C20D—H20G···O1Cii0.962.503.175 (3)128
C2OA—H2OC···Cg1iii0.962.753.4628 (19)131
C16C—H16F···Cg20.962.783.744 (2)171
C20B—H20C···Cg2i0.962.943.5787 (19)125
C16A—H16B···Cg3iv0.962.903.860 (2)170
C20C—H20F···Cg3ii0.962.773.4943 (19)132
C16B—H16D···Cg40.962.863.818 (2)171
C20D—H20I···Cg4v0.962.963.5557 (19)122
Symmetry codes: (i) x+1, y+2, z+2; (ii) x+2, y+1, z+1; (iii) x, y+2, z+2; (iv) x1, y, z; (v) x+1, y+1, z+1.
 

Footnotes

Permanent address: Department of Physics, Karunya University, Karunya Nagar, Coimbatore 641 114, India.

Acknowledgements

FHK and SRJ thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. SRJ thanks Universiti Sains Malaysia for a post–doctoral research fellowship. HKF also thanks Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CrossRef Web of Science Google Scholar
First citationAmir, M. & Kumar, S. (2007). Acta Pharm. 57, 31–45.  CrossRef PubMed CAS Google Scholar
First citationBedia, K.-K., Elçin, O., Seda, U., Fatma, K., Nathaly, S., Sevim, R. & Dimoglo, A. (2006). Eur. J. Med. Chem. 41, 1253–1261.  Web of Science CrossRef PubMed CAS Google Scholar
First citationBruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationRollas, S., Gülerman, N. & Erdeniz, H. (2002). Farmaco, 57, 171–174.  Web of Science CrossRef PubMed CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2003). J. Appl. Cryst. 36, 7–13.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSridhar, R. & Perumal, T. (2003). Synth. Commun. 33, 1483–1488.  Web of Science CrossRef CAS Google Scholar
First citationTerzioglu, N. & Gursoy, A. (2003). Eur. J. Med. Chem. 38, 781–786.  Web of Science CrossRef PubMed CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 65| Part 1| January 2009| Pages o17-o18
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds