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ISSN: 2056-9890

N-[2-(4-Methyl-2-quinol­yl)phen­yl]acetamide: a P1 structure with Z = 4

aOrganic and Medicinal Chemistry Research Laboratory, Organic Chemistry Division, School of Advanced Sciences, VIT University, Vellore 632 014, Tamil Nadu, India, bSolid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore 560 012, Karnataka, India, and cDepartment of Physics, Faculty of Arts and Sciences, Erciyes University, 38039 Kayseri, Turkey
*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 2 July 2010; accepted 12 July 2010; online 17 July 2010)

The title compound, C18H16N2O, crystallizes in the triclinic space group P1, with four independent mol­ecules in the asymmetric unit wherein two mol­ecules have an irregular -ac, -ac, +ap conformation (ap, antiperiplanar; ac, anticlinal), while the other mol­ecules exhibit a different, +ac, +ac, +ap conformation. The planar (r.m.s. deviation = 0.006 Å in each of the four molecules) quinoline ring systems of the four mol­ecules are oriented at dihedral angles of 32.8 (2), 33.4 (2), 31.7 (2) and 32.3 (2)° with respect to the benzene rings. Intra­molecular N—H⋯N inter­actions occur in all four independent mol­ecules. The crystal packing is stabilized by inter­molecular N—H⋯O and C—H⋯O hydrogen bonds, and are further consolidated by C—H⋯π and ππ stacking inter­actions [centroid–centroid distances = 3.728 (3), 3.722 (3), 3.758 (3) and 3.705 (3) Å].

Related literature

For the biological activity of quinolines, see: Roopan & Khan (2009[Roopan, S. M. & Khan, F. N. (2009). ARKIVOC, pp. 161-169.]); Roopan et al. (2010[Roopan, S. M., Khan, F. N. & Mandel, B. K. (2010). Tetrahedron Lett. 51, 2309-2311.]); Yates (1984[Yates, F. S. (1984). Comprehensive Heterocyclic Chemistry, edited by A. R. Katritzky & C. W. Rees, Vol. 2, pp. 511-523. Oxford: Pergamon Press.]). For the crystal structures of substituted quinolines, see: Khan et al. (2010[Khan, F. N., Roopan, S. M., Hathwar, V. R. & Akkurt, M. (2010). Acta Cryst. E66, o972-o973.]); Kushwaha et al. (2010[Kushwaha, A. K., Roopan, S. M., Khan, F. N., Hathwar, V. R. & Akkurt, M. (2010). Acta Cryst. E66, o1049.]); Subashini et al. (2009[Subashini, R. R., Hathwar, V., Maiyalagan, T., Reddy, G. G. K. & Khan, F. N. (2009). Acta Cryst. E65, o1800-o1801.]). For another crystal structure with Z′ = 4 in space group P1, see: Bernès et al. (2003[Bernès, S., Torrens, H., López-Giral, A. & Buttenklepper, A. (2003). Acta Cryst. E59, o1372-o1375.]).

[Scheme 1]

Experimental

Crystal data
  • C18H16N2O

  • Mr = 276.33

  • Triclinic, P 1

  • a = 9.7383 (5) Å

  • b = 9.9035 (6) Å

  • c = 15.2809 (9) Å

  • α = 101.414 (5)°

  • β = 99.188 (5)°

  • γ = 90.065 (5)°

  • V = 1425.24 (14) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 295 K

  • 0.20 × 0.10 × 0.10 mm

Data collection
  • Oxford Xcalibur Eos(Nova) CCD detector diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO CCD and CrysAlis PRO RED. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.984, Tmax = 0.992

  • 29328 measured reflections

  • 5290 independent reflections

  • 3314 reflections with I > 2σ(I)

  • Rint = 0.079

Refinement
  • R[F2 > 2σ(F2)] = 0.058

  • wR(F2) = 0.164

  • S = 0.94

  • 5290 reflections

  • 766 parameters

  • 3 restraints

  • H-atom parameters constrained

  • Δρmax = 0.23 e Å−3

  • Δρmin = −0.24 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg3, Cg7, Cg11, Cg15 are the centroids of the C11–C16, C29–C34, C47–C52 and C65–C70 rings, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
N2—H2N⋯O4i 0.86 2.42 3.181 (6) 148
N2—H2N⋯N1 0.86 2.25 2.741 (7) 117
N4—H4N⋯O3ii 0.86 2.39 3.160 (6) 149
N4—H4N⋯N3 0.86 2.25 2.735 (7) 116
N6—H6N⋯O2iii 0.86 2.51 3.262 (6) 147
N6—H6N⋯N5 0.86 2.21 2.703 (7) 116
N8—H8N⋯O1 0.86 2.49 3.239 (6) 146
N8—H8N⋯N7 0.86 2.20 2.705 (7) 118
C36—H36B⋯O3ii 0.96 2.31 3.201 (7) 154
C44—H44⋯O2iii 0.93 2.60 3.472 (9) 157
C54—H54B⋯O2iii 0.96 2.28 3.213 (8) 162
C10—H10ACg15iv 0.96 2.76 3.586 (7) 145
C28—H28BCg11 0.96 2.63 3.579 (7) 171
C46—H46CCg7i 0.96 2.65 3.594 (7) 168
C64—H64CCg3v 0.96 2.65 3.604 (7) 173
Symmetry codes: (i) x+1, y, z; (ii) x, y-1, z; (iii) x+1, y+1, z; (iv) x+1, y-1, z; (v) x, y+1, z.

Data collection: CrysAlis PRO CCD (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO CCD and CrysAlis PRO RED. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO CCD; data reduction: CrysAlis PRO RED (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO CCD and CrysAlis PRO RED. Oxford Diffraction Ltd, Yarnton, England.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information


Comment top

Quinolines and their derivatives occur in numerous natural products, many of which possess interesting physiological and biological properties. Quinoline derivatives have been developed for the treatment of many diseases like malaria, HIV, tumor, and antibacterial infections (Yates, 1984). Since the turn of the century, the development of concise and effective methodologies for the preparation of libraries of small molecules for research in drug discovery has remained a major challenge. A number of strategies have been developed to address this challenge (Roopan et al., 2009, Roopan et al., 2010). We herewith reporting the synthesis of 2-substituted quinoline using 1-(2-aminophenyl)ethanone in acetic acid and drop of sulphuric acid at 453 K.

The title compound crystallizes in the triclinic space group P 1 with four independent molecules, A, B, C and D with O1, O2, O3 and O4, respectively, in the asymmetric unit (Figs. 1-4) with no evidence of pseudo- or non-crystallographic symmetry. Crystals belonging to this class, namely Z' = 4 in space group P 1, are not uncommon (Bernés et al., 2003). The molecules A and B have an irregular -ac, -ac, +ap conformation (C2-C1-C11-C16, C11-C16-N2-C17, C16-N2-C17-C18 in molecule A and C20-C19-C29-C34, C29-C34-N4-C35, C34-N4-C35-C36 in molecule B) while the other molecules C and D exhibit a different, +ac, +ac, +ap conformation (C38-C37-C47-C52, C47-C52-N6-C53, C52-N6-C53-C54 in molecule C and C56-C55-C65-C70, C65-C70-N8-C71, C70-N8-C71-C72 in molecule D). The planar quinoline ring system of each molecule makes a dihedral angle of 32.8 (2)° for A, 33.4 (2)° for B, 31.7 (2)° for C and 32.3 (2)° for D with the benzene ring [C11–C16 for A, C29–C34 for B, C47–C52 for C and C65–C70 for D] bound to it.

The crystal packing is stabilized by intermolecular N—H···O and C—H···O hydrogen bonds (Table 1, Fig. 5), and are further consolidated by C—H···π (Table 1) and π-π stacking interactions [Cg1···Cg14(x, -1 + y, z) = 3.728 (3), Cg2···Cg13 (1 + x, -1 + y, z) = 3.722 (3), Cg5···Cg10(-1 + x, y, z) = 3.758 (3), Cg6···Cg9(x, y, z) = 3.705 (3) Å; where Cg1, Cg2, Cg5, Cg6, Cg9, Cg10, Cg13 and Cg14 are the centroids of N1/C1–C4/C9, C4–C9, N3/C19–C22/C27, C22–C27, N5/C37–C40/C45, C40–C45, N7/C55–C58/C63 and C58–C63 rings, respectively].

Related literature top

For the biological activity of quinolines, see: Roopan & Khan (2009); Roopan et al. (2010); Yates (1984). For the crystal structures of substituted quinolines, see: Khan et al. (2010); Kushwaha et al. (2010); Subashini et al. (2009). For a crystal structure with Z' = 4 in space group P1, see: Bernès et al. (2003).

Experimental top

About 1 mmol of 2-aminoacetophenone in 10 ml of glacial acetic acid and 2 drops of concentrated sulfuric acid were refluxed at 393 K for 8 h. After the completion of the reaction (monitored by TLC) the mixture was poured in to crushed ice to afford the crude product which was purified by column chromatography on silica gel. The pure compound was dissolved in ethanol to get single crystals.

Refinement top

An analysis of the E-statistics indicated the structure to be non-centrosymmetric. The centrosymmetric space group P -1 was attempted but it was not successful. However, the crystal was twinned and TWIN and BASF instructions were used in the refinement procedure. The H atoms were positioned geometrically with N—H = 0.86 Å, C—H = 0.93 and 0.96 Å, and refined a riding model, with Uiso(H) = 1.2–1.5Ueq(C). In the absence of significant anomalous dispersion effects, Freidel pairs were merged using the MERG 4 command in SHELXL97; Sheldrick, 2008).

Structure description top

Quinolines and their derivatives occur in numerous natural products, many of which possess interesting physiological and biological properties. Quinoline derivatives have been developed for the treatment of many diseases like malaria, HIV, tumor, and antibacterial infections (Yates, 1984). Since the turn of the century, the development of concise and effective methodologies for the preparation of libraries of small molecules for research in drug discovery has remained a major challenge. A number of strategies have been developed to address this challenge (Roopan et al., 2009, Roopan et al., 2010). We herewith reporting the synthesis of 2-substituted quinoline using 1-(2-aminophenyl)ethanone in acetic acid and drop of sulphuric acid at 453 K.

The title compound crystallizes in the triclinic space group P 1 with four independent molecules, A, B, C and D with O1, O2, O3 and O4, respectively, in the asymmetric unit (Figs. 1-4) with no evidence of pseudo- or non-crystallographic symmetry. Crystals belonging to this class, namely Z' = 4 in space group P 1, are not uncommon (Bernés et al., 2003). The molecules A and B have an irregular -ac, -ac, +ap conformation (C2-C1-C11-C16, C11-C16-N2-C17, C16-N2-C17-C18 in molecule A and C20-C19-C29-C34, C29-C34-N4-C35, C34-N4-C35-C36 in molecule B) while the other molecules C and D exhibit a different, +ac, +ac, +ap conformation (C38-C37-C47-C52, C47-C52-N6-C53, C52-N6-C53-C54 in molecule C and C56-C55-C65-C70, C65-C70-N8-C71, C70-N8-C71-C72 in molecule D). The planar quinoline ring system of each molecule makes a dihedral angle of 32.8 (2)° for A, 33.4 (2)° for B, 31.7 (2)° for C and 32.3 (2)° for D with the benzene ring [C11–C16 for A, C29–C34 for B, C47–C52 for C and C65–C70 for D] bound to it.

The crystal packing is stabilized by intermolecular N—H···O and C—H···O hydrogen bonds (Table 1, Fig. 5), and are further consolidated by C—H···π (Table 1) and π-π stacking interactions [Cg1···Cg14(x, -1 + y, z) = 3.728 (3), Cg2···Cg13 (1 + x, -1 + y, z) = 3.722 (3), Cg5···Cg10(-1 + x, y, z) = 3.758 (3), Cg6···Cg9(x, y, z) = 3.705 (3) Å; where Cg1, Cg2, Cg5, Cg6, Cg9, Cg10, Cg13 and Cg14 are the centroids of N1/C1–C4/C9, C4–C9, N3/C19–C22/C27, C22–C27, N5/C37–C40/C45, C40–C45, N7/C55–C58/C63 and C58–C63 rings, respectively].

For the biological activity of quinolines, see: Roopan & Khan (2009); Roopan et al. (2010); Yates (1984). For the crystal structures of substituted quinolines, see: Khan et al. (2010); Kushwaha et al. (2010); Subashini et al. (2009). For a crystal structure with Z' = 4 in space group P1, see: Bernès et al. (2003).

Computing details top

Data collection: CrysAlis PRO CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO CCD (Oxford Diffraction, 2009); data reduction: CrysAlis PRO RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. The molecular structure of molecule A of the title compound; displacement ellipsoids drawn at the 50% probability level.
[Figure 2] Fig. 2. The molecular structure of molecule B of the title compound; displacement ellipsoids drawn at the 50% probability level.
[Figure 3] Fig. 3. The molecular structure of molecule C of the title compound; displacement ellipsoids drawn at the 50% probability level.
[Figure 4] Fig. 4. The molecular structure of molecule D of the title compound; displacement ellipsoids drawn at the 50% probability level.
[Figure 5] Fig. 5. Molecular packing and the hydrogen bonding of the title compound viewed down a axis. H atoms not involved in the intermolecular interactions (dashed lines) have been omitted for clarity.
N-[2-(4-Methyl-2-quinolyl)phenyl]acetamide top
Crystal data top
C18H16N2OZ = 4
Mr = 276.33F(000) = 584
Triclinic, P1Dx = 1.288 Mg m3
Hall symbol: P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.7383 (5) ÅCell parameters from 1432 reflections
b = 9.9035 (6) Åθ = 2.0–20.5°
c = 15.2809 (9) ŵ = 0.08 mm1
α = 101.414 (5)°T = 295 K
β = 99.188 (5)°Block, colourless
γ = 90.065 (5)°0.20 × 0.10 × 0.10 mm
V = 1425.24 (14) Å3
Data collection top
Oxford Xcalibur Eos(Nova) CCD detector
diffractometer
5290 independent reflections
Radiation source: Enhance (Mo) X-ray Source3314 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.079
ω scansθmax = 25.5°, θmin = 2.7°
Absorption correction: multi-scan
(CrysAlis PRO RED; Oxford Diffraction, 2009)
h = 1111
Tmin = 0.984, Tmax = 0.992k = 1111
29328 measured reflectionsl = 1818
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)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.164H-atom parameters constrained
S = 0.94 w = 1/[σ2(Fo2) + (0.1055P)2]
where P = (Fo2 + 2Fc2)/3
5290 reflections(Δ/σ)max < 0.001
766 parametersΔρmax = 0.23 e Å3
3 restraintsΔρmin = 0.24 e Å3
Crystal data top
C18H16N2Oγ = 90.065 (5)°
Mr = 276.33V = 1425.24 (14) Å3
Triclinic, P1Z = 4
a = 9.7383 (5) ÅMo Kα radiation
b = 9.9035 (6) ŵ = 0.08 mm1
c = 15.2809 (9) ÅT = 295 K
α = 101.414 (5)°0.20 × 0.10 × 0.10 mm
β = 99.188 (5)°
Data collection top
Oxford Xcalibur Eos(Nova) CCD detector
diffractometer
5290 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO RED; Oxford Diffraction, 2009)
3314 reflections with I > 2σ(I)
Tmin = 0.984, Tmax = 0.992Rint = 0.079
29328 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0583 restraints
wR(F2) = 0.164H-atom parameters constrained
S = 0.94Δρmax = 0.23 e Å3
5290 reflectionsΔρmin = 0.24 e Å3
766 parameters
Special details top

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

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
O10.5433 (4)0.3283 (5)0.0893 (3)0.0679 (16)
N10.9301 (5)0.0670 (5)0.0014 (3)0.0477 (17)
N20.7568 (5)0.2789 (5)0.0233 (3)0.0479 (17)
C10.8509 (5)0.0467 (6)0.0608 (4)0.0447 (19)
C20.8302 (6)0.0875 (6)0.0787 (4)0.049 (2)
C30.8889 (5)0.2001 (6)0.0339 (4)0.050 (2)
C40.9720 (5)0.1799 (6)0.0317 (4)0.0468 (19)
C51.0340 (6)0.2906 (7)0.0856 (4)0.058 (2)
C61.1092 (7)0.2636 (7)0.1487 (4)0.064 (3)
C71.1259 (7)0.1275 (7)0.1600 (4)0.063 (3)
C81.0672 (6)0.0231 (7)0.1108 (4)0.057 (2)
C90.9890 (5)0.0465 (6)0.0459 (4)0.047 (2)
C100.8644 (7)0.3407 (7)0.0521 (5)0.066 (3)
C110.7762 (6)0.1633 (5)0.1048 (4)0.0446 (17)
C120.7446 (7)0.1650 (6)0.1914 (4)0.057 (2)
C130.6635 (7)0.2636 (8)0.2323 (4)0.065 (3)
C140.6128 (7)0.3667 (7)0.1878 (4)0.062 (2)
C150.6434 (6)0.3709 (6)0.1040 (4)0.0507 (19)
C160.7258 (5)0.2726 (6)0.0623 (4)0.0442 (17)
C170.6659 (6)0.3079 (6)0.0933 (4)0.049 (2)
C180.7213 (6)0.3083 (8)0.1781 (4)0.066 (2)
O20.2107 (4)0.0456 (6)0.5805 (3)0.0728 (18)
N30.5519 (5)0.3067 (5)0.4898 (3)0.0489 (17)
N40.3917 (5)0.0960 (5)0.5163 (3)0.0500 (17)
C190.4453 (6)0.3265 (6)0.4306 (4)0.0429 (17)
C200.4127 (6)0.4601 (6)0.4125 (4)0.051 (2)
C210.4952 (6)0.5736 (6)0.4563 (4)0.0477 (19)
C220.6121 (5)0.5530 (6)0.5222 (4)0.0435 (17)
C230.7021 (7)0.6627 (7)0.5749 (4)0.059 (2)
C240.8104 (7)0.6361 (7)0.6365 (4)0.063 (3)
C250.8316 (6)0.5019 (7)0.6502 (4)0.061 (3)
C260.7462 (6)0.3954 (7)0.6017 (4)0.057 (2)
C270.6368 (6)0.4191 (5)0.5363 (4)0.0437 (17)
C280.4617 (7)0.7137 (6)0.4391 (5)0.068 (3)
C290.3475 (6)0.2082 (6)0.3856 (4)0.0465 (19)
C300.2745 (7)0.2048 (7)0.2995 (4)0.061 (2)
C310.1718 (7)0.1061 (8)0.2583 (5)0.070 (3)
C320.1437 (7)0.0043 (7)0.3041 (5)0.065 (3)
C330.2144 (6)0.0003 (6)0.3879 (4)0.0527 (19)
C340.3185 (5)0.1019 (6)0.4296 (4)0.050 (2)
C350.3340 (6)0.0675 (6)0.5860 (4)0.051 (2)
C360.4340 (6)0.0684 (8)0.6700 (4)0.066 (3)
O30.7086 (4)1.0413 (5)0.5781 (3)0.0692 (16)
N51.0455 (4)0.7212 (5)0.4866 (3)0.0451 (16)
N60.8859 (5)0.9444 (5)0.5108 (3)0.0479 (16)
C370.9378 (5)0.6617 (6)0.4268 (3)0.0423 (17)
C380.9110 (6)0.5172 (6)0.4096 (4)0.0480 (17)
C390.9949 (6)0.4330 (6)0.4534 (4)0.050 (2)
C401.1085 (6)0.4948 (6)0.5202 (4)0.0474 (19)
C411.1998 (7)0.4191 (7)0.5722 (4)0.057 (2)
C421.3077 (7)0.4881 (8)0.6362 (5)0.064 (3)
C431.3243 (6)0.6285 (8)0.6493 (4)0.064 (3)
C441.2377 (6)0.7027 (7)0.5996 (4)0.054 (2)
C451.1293 (5)0.6383 (6)0.5340 (4)0.0441 (19)
C460.9622 (7)0.2814 (7)0.4362 (5)0.069 (3)
C470.8399 (6)0.7511 (6)0.3819 (4)0.0448 (17)
C480.7663 (7)0.7020 (7)0.2959 (4)0.057 (2)
C490.6643 (7)0.7741 (8)0.2551 (4)0.067 (3)
C500.6357 (6)0.9044 (7)0.2999 (5)0.061 (3)
C510.7087 (6)0.9602 (7)0.3832 (4)0.053 (2)
C520.8113 (5)0.8866 (6)0.4248 (4)0.0446 (17)
C530.8323 (6)1.0137 (6)0.5815 (4)0.050 (2)
C540.9305 (7)1.0539 (8)0.6673 (4)0.070 (3)
O40.0423 (4)0.3327 (6)0.0889 (3)0.0733 (18)
N70.4267 (5)0.6515 (5)0.0017 (3)0.0443 (16)
N80.2536 (5)0.4286 (5)0.0231 (3)0.0471 (16)
C550.3477 (6)0.7108 (6)0.0610 (3)0.0449 (17)
C560.3282 (6)0.8550 (6)0.0788 (4)0.049 (2)
C570.3881 (6)0.9399 (6)0.0347 (4)0.0529 (19)
C580.4710 (5)0.8799 (6)0.0307 (4)0.0443 (19)
C590.5375 (6)0.9536 (7)0.0836 (5)0.060 (2)
C600.6132 (6)0.8888 (7)0.1453 (4)0.060 (3)
C610.6281 (6)0.7468 (8)0.1591 (4)0.060 (2)
C620.5646 (6)0.6722 (7)0.1089 (4)0.056 (2)
C630.4868 (5)0.7360 (6)0.0448 (4)0.0447 (19)
C640.3641 (7)1.0908 (7)0.0524 (5)0.069 (3)
C650.2726 (5)0.6201 (5)0.1057 (3)0.0419 (17)
C660.2424 (6)0.6714 (7)0.1922 (4)0.058 (2)
C670.1606 (7)0.5957 (8)0.2330 (4)0.064 (3)
C680.1105 (7)0.4662 (7)0.1882 (5)0.062 (3)
C690.1415 (6)0.4109 (6)0.1048 (4)0.0527 (19)
C700.2233 (5)0.4852 (6)0.0627 (4)0.0461 (19)
C710.1644 (6)0.3579 (6)0.0941 (4)0.050 (2)
C720.2186 (7)0.3182 (8)0.1798 (5)0.067 (3)
H20.775700.098300.121700.0580*
H2N0.840800.263000.032100.0580*
H51.023000.380500.077800.0690*
H61.149400.335200.184100.0770*
H71.178600.109600.202400.0760*
H81.078600.066000.119900.0680*
H10A0.933000.356200.101400.0990*
H10B0.871200.409000.001000.0990*
H10C0.773200.346900.067700.0990*
H120.779700.097100.222100.0680*
H130.642900.261200.289300.0770*
H140.557600.433600.215000.0750*
H150.608500.440500.074800.0610*
H18A0.645400.306600.226900.0980*
H18B0.776000.228500.191500.0980*
H18C0.778500.390000.171000.0980*
H4N0.480200.111900.525700.0600*
H200.334800.470200.370700.0620*
H230.687000.752600.567200.0710*
H240.870600.707700.669700.0750*
H250.905300.485200.693100.0730*
H260.760600.306800.612100.0680*
H28A0.370300.711100.404100.1020*
H28B0.528600.743100.406300.1020*
H28C0.464600.777200.495700.1020*
H300.295600.271700.268200.0730*
H310.122500.107800.201200.0840*
H320.074900.062900.277000.0780*
H330.194100.069100.417400.0630*
H36A0.412600.141100.717100.0980*
H36B0.526800.083300.659300.0980*
H36C0.427300.018500.688100.0980*
H6N0.974400.934300.518900.0570*
H380.834300.479000.367500.0580*
H411.187800.324000.563700.0690*
H421.368800.438800.670100.0780*
H431.395900.673700.693000.0770*
H441.251100.797900.609600.0650*
H46A0.886300.257800.386800.1030*
H46B0.936600.257600.489500.1030*
H46C1.042600.231700.421200.1030*
H480.787300.616100.264600.0690*
H490.614700.736500.198300.0800*
H500.566100.954200.272900.0740*
H510.689401.048300.412100.0640*
H54A0.910001.144400.697500.1050*
H54B1.024001.054400.654700.1050*
H54C0.921500.989200.705300.1050*
H8N0.337800.440100.031400.0560*
H560.273200.892300.121500.0590*
H590.529001.048600.075700.0720*
H600.655900.939800.179100.0710*
H610.680300.702900.201700.0730*
H620.574000.577300.118100.0670*
H64A0.293601.110300.090000.1040*
H64B0.334301.119300.003900.1040*
H64C0.449101.140000.082500.1040*
H660.277700.758100.223100.0690*
H670.139800.632100.290200.0770*
H680.054900.415700.215100.0740*
H690.107800.322800.075800.0630*
H72A0.240600.222500.189000.1010*
H72B0.301000.373000.177400.1010*
H72C0.149500.333400.228900.1010*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.037 (2)0.086 (3)0.087 (3)0.012 (2)0.013 (2)0.030 (3)
N10.042 (3)0.044 (3)0.059 (3)0.001 (2)0.009 (2)0.014 (2)
N20.041 (3)0.050 (3)0.056 (3)0.000 (2)0.010 (2)0.017 (2)
C10.034 (3)0.053 (4)0.045 (3)0.003 (3)0.001 (2)0.011 (3)
C20.040 (3)0.050 (4)0.059 (4)0.003 (3)0.007 (3)0.019 (3)
C30.036 (3)0.051 (4)0.062 (4)0.001 (3)0.003 (3)0.021 (3)
C40.033 (3)0.054 (4)0.050 (3)0.008 (3)0.003 (2)0.010 (3)
C50.050 (4)0.049 (4)0.069 (4)0.010 (3)0.007 (3)0.014 (3)
C60.064 (4)0.062 (5)0.065 (4)0.027 (3)0.014 (3)0.007 (3)
C70.052 (4)0.071 (5)0.067 (4)0.007 (3)0.014 (3)0.015 (4)
C80.050 (4)0.063 (4)0.061 (4)0.002 (3)0.011 (3)0.016 (3)
C90.033 (3)0.050 (4)0.055 (4)0.007 (3)0.005 (3)0.012 (3)
C100.059 (4)0.055 (4)0.091 (5)0.002 (3)0.009 (4)0.034 (4)
C110.044 (3)0.038 (3)0.050 (3)0.001 (2)0.006 (3)0.006 (3)
C120.063 (4)0.046 (4)0.059 (4)0.004 (3)0.007 (3)0.009 (3)
C130.067 (4)0.075 (5)0.051 (4)0.010 (4)0.022 (3)0.001 (3)
C140.060 (4)0.056 (4)0.067 (4)0.005 (3)0.025 (3)0.008 (3)
C150.044 (3)0.036 (3)0.072 (4)0.001 (3)0.014 (3)0.007 (3)
C160.036 (3)0.038 (3)0.057 (3)0.006 (2)0.007 (2)0.006 (3)
C170.046 (4)0.045 (3)0.059 (4)0.003 (3)0.006 (3)0.017 (3)
C180.047 (3)0.091 (5)0.061 (4)0.011 (3)0.011 (3)0.017 (3)
O20.038 (2)0.097 (4)0.090 (3)0.011 (2)0.015 (2)0.031 (3)
N30.043 (3)0.052 (3)0.056 (3)0.001 (2)0.011 (2)0.019 (2)
N40.039 (3)0.048 (3)0.067 (3)0.004 (2)0.013 (2)0.018 (2)
C190.042 (3)0.045 (3)0.047 (3)0.002 (3)0.018 (3)0.013 (3)
C200.051 (3)0.051 (4)0.058 (4)0.000 (3)0.015 (3)0.021 (3)
C210.048 (3)0.040 (3)0.064 (4)0.001 (3)0.025 (3)0.019 (3)
C220.040 (3)0.047 (3)0.050 (3)0.003 (3)0.020 (3)0.015 (3)
C230.056 (4)0.049 (4)0.079 (4)0.003 (3)0.027 (4)0.018 (3)
C240.056 (4)0.069 (5)0.064 (4)0.022 (3)0.014 (3)0.011 (3)
C250.052 (4)0.072 (5)0.059 (4)0.012 (3)0.005 (3)0.014 (3)
C260.045 (3)0.059 (4)0.072 (4)0.002 (3)0.017 (3)0.022 (3)
C270.044 (3)0.040 (3)0.052 (3)0.005 (3)0.020 (3)0.011 (3)
C280.070 (4)0.048 (4)0.095 (5)0.001 (3)0.020 (4)0.030 (4)
C290.041 (3)0.046 (3)0.054 (4)0.011 (3)0.012 (3)0.010 (3)
C300.063 (4)0.059 (4)0.061 (4)0.000 (3)0.011 (3)0.010 (3)
C310.062 (4)0.071 (5)0.064 (4)0.005 (4)0.006 (3)0.003 (4)
C320.060 (4)0.051 (4)0.077 (5)0.005 (3)0.006 (4)0.000 (3)
C330.042 (3)0.040 (3)0.074 (4)0.005 (3)0.010 (3)0.006 (3)
C340.037 (3)0.051 (4)0.059 (4)0.011 (3)0.008 (3)0.007 (3)
C350.046 (4)0.037 (3)0.074 (4)0.002 (3)0.013 (3)0.018 (3)
C360.051 (4)0.086 (5)0.063 (4)0.006 (3)0.010 (3)0.022 (4)
O30.036 (2)0.081 (3)0.087 (3)0.014 (2)0.014 (2)0.005 (2)
N50.039 (2)0.043 (3)0.055 (3)0.001 (2)0.013 (2)0.010 (2)
N60.035 (2)0.047 (3)0.060 (3)0.002 (2)0.006 (2)0.008 (2)
C370.040 (3)0.046 (3)0.042 (3)0.001 (3)0.011 (2)0.008 (2)
C380.043 (3)0.046 (3)0.052 (3)0.000 (3)0.012 (3)0.001 (3)
C390.054 (4)0.041 (3)0.058 (4)0.009 (3)0.020 (3)0.007 (3)
C400.043 (3)0.053 (4)0.052 (3)0.013 (3)0.021 (3)0.014 (3)
C410.059 (4)0.048 (4)0.074 (4)0.013 (3)0.029 (3)0.019 (3)
C420.051 (4)0.079 (5)0.072 (4)0.016 (4)0.012 (3)0.035 (4)
C430.043 (3)0.086 (6)0.064 (4)0.000 (3)0.008 (3)0.020 (4)
C440.043 (3)0.053 (4)0.068 (4)0.005 (3)0.009 (3)0.014 (3)
C450.036 (3)0.047 (4)0.054 (3)0.007 (3)0.017 (3)0.014 (3)
C460.075 (5)0.045 (4)0.085 (5)0.002 (3)0.015 (4)0.010 (3)
C470.041 (3)0.046 (3)0.050 (3)0.001 (3)0.009 (3)0.015 (3)
C480.062 (4)0.056 (4)0.055 (4)0.001 (3)0.010 (3)0.015 (3)
C490.060 (4)0.081 (5)0.059 (4)0.015 (4)0.010 (3)0.028 (4)
C500.052 (4)0.064 (5)0.075 (4)0.002 (3)0.001 (3)0.038 (4)
C510.047 (3)0.055 (4)0.065 (4)0.002 (3)0.007 (3)0.030 (3)
C520.042 (3)0.040 (3)0.054 (3)0.006 (3)0.011 (3)0.012 (3)
C530.047 (4)0.040 (3)0.063 (4)0.001 (3)0.015 (3)0.009 (3)
C540.054 (4)0.088 (5)0.061 (4)0.013 (4)0.011 (3)0.004 (4)
O40.037 (2)0.096 (4)0.085 (3)0.015 (2)0.013 (2)0.011 (3)
N70.040 (2)0.039 (3)0.054 (3)0.001 (2)0.007 (2)0.010 (2)
N80.041 (2)0.042 (3)0.059 (3)0.003 (2)0.014 (2)0.007 (2)
C550.042 (3)0.047 (3)0.045 (3)0.003 (3)0.007 (3)0.008 (3)
C560.045 (3)0.046 (4)0.057 (4)0.005 (3)0.011 (3)0.008 (3)
C570.046 (3)0.043 (3)0.066 (4)0.008 (3)0.001 (3)0.009 (3)
C580.032 (3)0.049 (4)0.048 (3)0.010 (2)0.005 (2)0.010 (3)
C590.049 (3)0.053 (4)0.076 (4)0.018 (3)0.003 (3)0.022 (3)
C600.052 (4)0.065 (5)0.066 (4)0.013 (3)0.006 (3)0.026 (3)
C610.040 (3)0.085 (5)0.061 (4)0.002 (3)0.014 (3)0.022 (4)
C620.045 (3)0.061 (4)0.062 (4)0.004 (3)0.007 (3)0.014 (3)
C630.032 (3)0.045 (4)0.056 (3)0.004 (3)0.000 (3)0.013 (3)
C640.059 (4)0.051 (4)0.097 (5)0.010 (3)0.014 (4)0.012 (4)
C650.038 (3)0.041 (3)0.047 (3)0.003 (2)0.008 (2)0.009 (3)
C660.058 (4)0.056 (4)0.060 (4)0.002 (3)0.014 (3)0.011 (3)
C670.066 (4)0.083 (5)0.052 (4)0.016 (4)0.021 (3)0.027 (4)
C680.059 (4)0.064 (5)0.074 (4)0.009 (3)0.023 (3)0.033 (4)
C690.049 (3)0.040 (3)0.075 (4)0.003 (3)0.016 (3)0.021 (3)
C700.041 (3)0.041 (3)0.058 (4)0.003 (3)0.007 (3)0.015 (3)
C710.040 (3)0.046 (4)0.062 (4)0.000 (3)0.006 (3)0.008 (3)
C720.047 (4)0.076 (5)0.074 (4)0.007 (3)0.010 (3)0.003 (3)
Geometric parameters (Å, º) top
O1—C171.220 (7)C25—H250.9300
O2—C351.207 (7)C26—H260.9300
O3—C531.231 (7)C28—H28A0.9600
O4—C711.233 (7)C28—H28B0.9600
N1—C91.388 (8)C28—H28C0.9600
N1—C11.325 (7)C30—H300.9300
N2—C171.353 (8)C31—H310.9300
N2—C161.402 (7)C32—H320.9300
N2—H2N0.8600C33—H330.9300
N3—C191.306 (8)C36—H36B0.9600
N3—C271.387 (7)C36—H36A0.9600
N4—C351.356 (8)C36—H36C0.9600
N4—C341.413 (7)C37—C471.482 (8)
N4—H4N0.8600C37—C381.419 (8)
N5—C451.383 (7)C38—C391.363 (8)
N5—C371.327 (6)C39—C461.497 (9)
N6—C531.341 (8)C39—C401.425 (8)
N6—C521.407 (7)C40—C451.404 (9)
N6—H6N0.8600C40—C411.413 (9)
N7—C631.384 (8)C41—C421.390 (10)
N7—C551.331 (7)C42—C431.371 (11)
N8—C711.349 (8)C43—C441.359 (9)
N8—C701.398 (7)C44—C451.391 (8)
N8—H8N0.8600C47—C481.387 (8)
C1—C111.472 (8)C47—C521.421 (8)
C1—C21.429 (9)C48—C491.366 (10)
C2—C31.365 (8)C49—C501.387 (10)
C3—C101.499 (9)C50—C511.365 (9)
C3—C41.428 (8)C51—C521.384 (8)
C4—C51.431 (9)C53—C541.478 (9)
C4—C91.394 (9)C38—H380.9300
C5—C61.366 (9)C41—H410.9300
C6—C71.405 (10)C42—H420.9300
C7—C81.339 (9)C43—H430.9300
C8—C91.396 (8)C44—H440.9300
C11—C121.403 (8)C46—H46B0.9600
C11—C161.419 (8)C46—H46A0.9600
C12—C131.373 (10)C46—H46C0.9600
C13—C141.385 (10)C48—H480.9300
C14—C151.369 (9)C49—H490.9300
C15—C161.385 (8)C50—H500.9300
C17—C181.482 (8)C51—H510.9300
C2—H20.9300C54—H54B0.9600
C5—H50.9300C54—H54A0.9600
C6—H60.9300C54—H54C0.9600
C7—H70.9300C55—C651.486 (8)
C8—H80.9300C55—C561.419 (8)
C10—H10A0.9600C56—C571.360 (8)
C10—H10C0.9600C57—C641.491 (9)
C10—H10B0.9600C57—C581.424 (8)
C12—H120.9300C58—C631.411 (9)
C13—H130.9300C58—C591.416 (9)
C14—H140.9300C59—C601.352 (9)
C15—H150.9300C60—C611.391 (11)
C18—H18A0.9600C61—C621.375 (9)
C18—H18B0.9600C62—C631.388 (8)
C18—H18C0.9600C65—C701.413 (8)
C19—C201.430 (9)C65—C661.397 (7)
C19—C291.491 (8)C66—C671.388 (10)
C20—C211.373 (8)C67—C681.377 (10)
C21—C221.438 (8)C68—C691.365 (9)
C21—C281.490 (9)C69—C701.393 (8)
C22—C231.422 (9)C71—C721.472 (9)
C22—C271.400 (8)C56—H560.9300
C23—C241.360 (9)C59—H590.9300
C24—C251.396 (10)C60—H600.9300
C25—C261.358 (9)C61—H610.9300
C26—C271.394 (8)C62—H620.9300
C29—C341.407 (8)C64—H64A0.9600
C29—C301.386 (8)C64—H64B0.9600
C30—C311.380 (10)C64—H64C0.9600
C31—C321.386 (11)C66—H660.9300
C32—C331.362 (9)C67—H670.9300
C33—C341.409 (8)C68—H680.9300
C35—C361.481 (8)C69—H690.9300
C20—H200.9300C72—H72A0.9600
C23—H230.9300C72—H72B0.9600
C24—H240.9300C72—H72C0.9600
O1···N83.239 (6)C59···H64B2.8400
O1···C152.905 (7)C59···H64C3.0700
O1···C723.236 (8)C61···H43xii2.9100
O2···N6i3.262 (6)C64···H592.7000
O2···C332.894 (7)C66···H562.6600
O2···C54i3.213 (8)C66···H10Av3.1000
O3···C512.927 (7)C67···H202.9600
O3···C36ii3.201 (7)C67···H28A3.0700
O3···N4ii3.160 (6)C67···H10Av2.8500
O4···C18iii3.193 (7)C68···H302.9500
O4···N2iii3.181 (6)C68···H10Av2.8400
O4···C692.911 (7)C69···H10Av3.0800
O1···H8N2.4900C71···H692.8200
O1···H152.5100C71···H8iii2.9400
O1···H72B2.6100C71···H5v2.9200
O1···H622.6100C72···H36Axiii3.0000
O1···H59iv2.8200H2···C122.6500
O2···H54Bi2.2800H2···H122.2100
O2···H332.5100H2···C49iv2.9400
O2···H44i2.6000H2···H10C2.4400
O2···H6Ni2.5100H2N···O4vi2.4200
O2···H41iii2.8300H2N···C12.7900
O3···H512.5300H2N···N12.2500
O3···H26ii2.6100H2N···H18B2.3700
O3···H4Nii2.3900H4N···H36B2.0900
O3···H36Bii2.3100H4N···C192.7900
O3···H232.8400H4N···O3iv2.3900
O4···H8iii2.6200H4N···N32.2500
O4···H5v2.8200H5···C71viii2.9200
O4···H692.5200H5···H10B2.0800
O4···H2Niii2.4200H5···C102.6700
O4···H18Ciii2.7800H5···O4viii2.8200
O4···H18Biii2.8800H6N···C372.7800
N1···N22.741 (7)H6N···O2vii2.5100
N2···O4vi3.181 (6)H6N···N52.2100
N2···N12.741 (7)H6N···H54B2.1600
N3···N42.735 (7)H8···O4vi2.6200
N4···O3iv3.160 (6)H8···C71vi2.9400
N4···N32.735 (7)H8N···O12.4900
N5···N62.703 (7)H8N···N72.2000
N6···O2vii3.262 (6)H8N···H72B2.1700
N6···N52.703 (7)H8N···C552.7700
N7···N82.705 (7)H10A···C69viii3.0800
N8···O13.239 (6)H10A···C66viii3.1000
N8···N72.705 (7)H10A···C67viii2.8500
N1···H2N2.2500H10A···C68viii2.8400
N3···H4N2.2500H10B···C52.6100
N5···H6N2.2100H10B···H52.0800
N7···H8N2.2000H10C···H22.4400
C1···C59iv3.474 (8)H12···C50iv2.9100
C2···C59iv3.548 (9)H12···H22.2100
C3···C61iv3.524 (8)H12···C22.6700
C4···C61iv3.590 (8)H13···C193.0900
C4···C56viii3.592 (8)H13···H46A2.5900
C5···C56viii3.586 (8)H15···C172.7900
C5···C55viii3.486 (8)H15···O12.5100
C7···C57viii3.550 (9)H18B···C54ix3.0800
C8···C64viii3.525 (9)H18B···H2N2.3700
C8···C57viii3.599 (8)H18B···H54Aix2.3300
C10···C62iv3.525 (9)H18B···O4vi2.8800
C12···C50iv3.575 (9)H18C···O4vi2.7800
C15···O12.905 (7)H20···H302.2500
C18···O4vi3.193 (7)H20···C302.6600
C19···C41iii3.480 (9)H20···H28A2.3500
C20···C40iii3.597 (8)H20···C672.9600
C20···C41iii3.525 (9)H23···O32.8400
C21···C43iii3.563 (8)H23···H28C2.3000
C22···C383.594 (8)H23···C282.6700
C23···C383.578 (9)H23···C532.9000
C23···C373.470 (8)H26···H54Aiv2.5800
C25···C403.589 (8)H26···O3iv2.6100
C25···C393.572 (8)H26···C53iv2.9500
C26···C463.559 (9)H28A···C673.0700
C28···C44iii3.550 (9)H28A···H202.3500
C33···O22.894 (7)H28B···C523.0400
C36···O3iv3.201 (7)H28B···C233.0900
C37···C233.470 (8)H28B···C483.0600
C38···C233.578 (9)H28B···C492.9000
C38···C223.594 (8)H28B···C502.8000
C39···C253.572 (8)H28B···C512.8800
C40···C20vi3.597 (8)H28C···H232.3000
C40···C253.589 (8)H28C···C44iii3.0900
C41···C20vi3.525 (9)H28C···C232.7800
C41···C19vi3.480 (9)H30···C682.9500
C43···C21vi3.563 (8)H30···H202.2500
C44···C28vi3.550 (9)H30···C202.6800
C46···C263.559 (9)H31···H64Aiv2.5700
C50···C12ii3.575 (9)H33···C352.8000
C51···O32.927 (7)H33···O22.5100
C54···O2vii3.213 (8)H36A···H72Ax2.4100
C55···C5v3.486 (8)H36A···C72x3.0000
C56···C5v3.586 (8)H36B···O3iv2.3100
C56···C4v3.592 (8)H36B···H4N2.0900
C57···C7v3.550 (9)H36C···H44i2.4800
C57···C8v3.599 (8)H38···H46A2.3100
C59···C2ii3.548 (9)H38···H482.2700
C59···C1ii3.474 (8)H38···C132.9600
C61···C4ii3.590 (8)H38···C482.6900
C61···C3ii3.524 (8)H41···C462.6700
C62···C10ii3.525 (9)H41···O2vi2.8300
C64···C8v3.525 (9)H41···C35vi2.9700
C69···O42.911 (7)H41···H46C2.4100
C72···O13.236 (8)H41···H46B2.5500
C1···H2N2.7900H43···C61xiv2.9100
C2···H122.6700H44···O2vii2.6000
C5···H10B2.6100H44···C35vii2.8900
C7···H54Cix3.0300H44···H36Cvii2.4800
C8···H64Bviii3.0200H46A···C123.0400
C8···H54Cix2.9600H46A···C132.9500
C10···H52.6700H46A···H382.3100
C12···H46A3.0400H46A···H132.5900
C12···H64Civ3.0700H46B···C262.8900
C12···H22.6500H46B···C412.9800
C13···H382.9600H46B···H412.5500
C13···H46A2.9500H46C···C31vi3.0200
C13···H64Civ2.9100H46C···C32vi2.8700
C14···H482.9300H46C···H412.4100
C14···H64Civ2.8100H46C···C412.8800
C15···H64Civ2.9000H46C···C34vi2.9800
C16···H64Civ3.0800H46C···C33vi2.8500
C17···H622.8900H48···H382.2700
C17···H152.7900H48···C382.7100
C17···H59iv2.9700H48···C142.9300
C18···H623.0800H49···C553.0500
C18···H54Aix3.0900H51···O32.5300
C19···H133.0900H51···C532.8200
C19···H4N2.7900H54A···H26ii2.5800
C20···H302.6800H54A···C18xi3.0900
C23···H28C2.7800H54A···H18Bxi2.3300
C23···H28B3.0900H54B···O2vii2.2800
C24···H61x2.9200H54B···H6N2.1600
C26···H46B2.8900H54C···C7xi3.0300
C28···H232.6700H54C···C8xi2.9600
C30···H202.6600H56···C31ii2.9600
C31···H64Aiv3.0100H56···C662.6600
C31···H46Ciii3.0200H56···H64A2.3200
C31···H56iv2.9600H56···H662.2300
C32···H66iv2.9200H59···O1ii2.8200
C32···H46Ciii2.8700H59···C17ii2.9700
C33···H46Ciii2.8500H59···C642.7000
C34···H46Ciii2.9800H59···H64B2.3800
C35···H332.8000H61···C24xiii2.9200
C35···H41iii2.9700H62···O12.6100
C35···H44i2.8900H62···C172.8900
C37···H6N2.7800H62···C183.0800
C37···H67vi3.0600H64A···C31ii3.0100
C38···H482.7100H64A···H31ii2.5700
C41···H46B2.9800H64A···H562.3200
C41···H46C2.8800H64B···C8v3.0200
C44···H28Cvi3.0900H64B···C592.8400
C46···H412.6700H64B···H592.3800
C48···H28B3.0600H64C···C12ii3.0700
C48···H382.6900H64C···C13ii2.9100
C49···H2ii2.9400H64C···C14ii2.8100
C49···H28B2.9000H64C···C15ii2.9000
C50···H12ii2.9100H64C···C16ii3.0800
C50···H28B2.8000H64C···C593.0700
C51···H28B2.8800H66···C32ii2.9200
C52···H28B3.0400H66···C562.6800
C53···H26ii2.9500H66···H562.2300
C53···H232.9000H67···C37iii3.0600
C53···H512.8200H69···O42.5200
C54···H18Bxi3.0800H69···C712.8200
C55···H493.0500H72A···H36Axiii2.4100
C55···H8N2.7700H72B···O12.6100
C56···H662.6800H72B···H8N2.1700
C1—N1—C9118.3 (5)C32—C33—H33120.00
C16—N2—C17125.6 (5)C34—C33—H33120.00
C17—N2—H2N117.00H36B—C36—H36C110.00
C16—N2—H2N117.00C35—C36—H36B109.00
C19—N3—C27118.8 (5)C35—C36—H36A109.00
C34—N4—C35125.4 (5)H36A—C36—H36C109.00
C34—N4—H4N117.00C35—C36—H36C109.00
C35—N4—H4N117.00H36A—C36—H36B109.00
C37—N5—C45117.9 (5)N5—C37—C38121.5 (5)
C52—N6—C53126.3 (5)N5—C37—C47118.3 (5)
C53—N6—H6N117.00C38—C37—C47120.1 (5)
C52—N6—H6N117.00C37—C38—C39121.6 (5)
C55—N7—C63117.2 (5)C38—C39—C46120.7 (6)
C70—N8—C71126.7 (5)C40—C39—C46121.2 (5)
C71—N8—H8N117.00C38—C39—C40118.0 (6)
C70—N8—H8N117.00C39—C40—C41123.3 (6)
N1—C1—C2121.3 (5)C41—C40—C45119.2 (5)
N1—C1—C11119.1 (5)C39—C40—C45117.5 (5)
C2—C1—C11119.6 (5)C40—C41—C42119.4 (6)
C1—C2—C3121.3 (5)C41—C42—C43120.2 (7)
C4—C3—C10121.3 (5)C42—C43—C44121.1 (6)
C2—C3—C4117.9 (5)C43—C44—C45120.9 (6)
C2—C3—C10120.8 (5)N5—C45—C40123.4 (5)
C3—C4—C9118.2 (5)N5—C45—C44117.3 (5)
C5—C4—C9118.7 (5)C40—C45—C44119.2 (6)
C3—C4—C5123.1 (6)C48—C47—C52116.7 (6)
C4—C5—C6119.7 (6)C37—C47—C48120.4 (5)
C5—C6—C7119.9 (6)C37—C47—C52122.8 (5)
C6—C7—C8121.1 (6)C47—C48—C49123.0 (6)
C7—C8—C9120.8 (6)C48—C49—C50118.9 (6)
C4—C9—C8119.8 (5)C49—C50—C51120.6 (6)
N1—C9—C8117.2 (5)C50—C51—C52120.4 (6)
N1—C9—C4123.0 (5)N6—C52—C47119.5 (5)
C1—C11—C12119.5 (5)N6—C52—C51120.2 (5)
C1—C11—C16123.6 (5)C47—C52—C51120.3 (5)
C12—C11—C16116.9 (5)N6—C53—C54116.1 (5)
C11—C12—C13122.2 (6)O3—C53—C54120.3 (6)
C12—C13—C14119.4 (6)O3—C53—N6123.6 (5)
C13—C14—C15120.5 (6)C37—C38—H38119.00
C14—C15—C16120.7 (6)C39—C38—H38119.00
N2—C16—C15120.0 (5)C40—C41—H41120.00
N2—C16—C11119.7 (5)C42—C41—H41120.00
C11—C16—C15120.3 (5)C43—C42—H42120.00
O1—C17—C18120.7 (5)C41—C42—H42120.00
O1—C17—N2122.8 (5)C42—C43—H43119.00
N2—C17—C18116.5 (5)C44—C43—H43119.00
C3—C2—H2119.00C43—C44—H44120.00
C1—C2—H2119.00C45—C44—H44120.00
C4—C5—H5120.00H46A—C46—H46C109.00
C6—C5—H5120.00C39—C46—H46C109.00
C7—C6—H6120.00H46A—C46—H46B109.00
C5—C6—H6120.00C39—C46—H46A109.00
C6—C7—H7119.00C39—C46—H46B109.00
C8—C7—H7119.00H46B—C46—H46C110.00
C9—C8—H8120.00C49—C48—H48119.00
C7—C8—H8120.00C47—C48—H48119.00
C3—C10—H10A109.00C48—C49—H49121.00
H10B—C10—H10C109.00C50—C49—H49120.00
H10A—C10—H10B110.00C51—C50—H50120.00
C3—C10—H10B110.00C49—C50—H50120.00
C3—C10—H10C109.00C50—C51—H51120.00
H10A—C10—H10C109.00C52—C51—H51120.00
C11—C12—H12119.00H54A—C54—H54C110.00
C13—C12—H12119.00H54B—C54—H54C109.00
C14—C13—H13120.00H54A—C54—H54B109.00
C12—C13—H13120.00C53—C54—H54A109.00
C15—C14—H14120.00C53—C54—H54B109.00
C13—C14—H14120.00C53—C54—H54C110.00
C16—C15—H15120.00C56—C55—C65119.8 (5)
C14—C15—H15120.00N7—C55—C56122.2 (5)
C17—C18—H18B110.00N7—C55—C65117.9 (5)
C17—C18—H18A110.00C55—C56—C57121.4 (5)
H18A—C18—H18B109.00C56—C57—C58118.1 (6)
H18A—C18—H18C109.00C56—C57—C64120.9 (6)
C17—C18—H18C110.00C58—C57—C64121.0 (6)
H18B—C18—H18C109.00C57—C58—C59124.9 (6)
N3—C19—C20122.3 (5)C59—C58—C63117.4 (5)
N3—C19—C29119.1 (5)C57—C58—C63117.7 (5)
C20—C19—C29118.5 (5)C58—C59—C60121.4 (6)
C19—C20—C21120.7 (5)C59—C60—C61120.9 (6)
C20—C21—C22117.5 (5)C60—C61—C62119.1 (6)
C20—C21—C28121.4 (6)C61—C62—C63121.2 (6)
C22—C21—C28121.2 (5)N7—C63—C58123.4 (5)
C21—C22—C23123.0 (6)C58—C63—C62119.9 (5)
C21—C22—C27118.4 (5)N7—C63—C62116.7 (6)
C23—C22—C27118.5 (5)C55—C65—C70122.9 (4)
C22—C23—C24120.0 (6)C66—C65—C70117.8 (5)
C23—C24—C25120.3 (6)C55—C65—C66119.3 (5)
C24—C25—C26120.9 (6)C65—C66—C67121.3 (6)
C25—C26—C27120.0 (6)C66—C67—C68119.5 (6)
N3—C27—C22122.4 (5)C67—C68—C69120.9 (6)
N3—C27—C26117.4 (5)C68—C69—C70120.6 (6)
C22—C27—C26120.2 (5)N8—C70—C69120.3 (5)
C30—C29—C34117.5 (6)C65—C70—C69119.9 (5)
C19—C29—C34122.4 (5)N8—C70—C65119.7 (5)
C19—C29—C30120.0 (6)N8—C71—C72116.4 (5)
C29—C30—C31122.6 (6)O4—C71—N8122.1 (5)
C30—C31—C32118.4 (7)O4—C71—C72121.5 (6)
C31—C32—C33121.6 (6)C55—C56—H56119.00
C32—C33—C34119.6 (6)C57—C56—H56119.00
N4—C34—C29120.8 (5)C58—C59—H59119.00
N4—C34—C33119.0 (5)C60—C59—H59119.00
C29—C34—C33120.2 (5)C59—C60—H60120.00
N4—C35—C36114.6 (5)C61—C60—H60119.00
O2—C35—N4122.7 (6)C60—C61—H61120.00
O2—C35—C36122.7 (6)C62—C61—H61120.00
C21—C20—H20120.00C61—C62—H62119.00
C19—C20—H20120.00C63—C62—H62119.00
C22—C23—H23120.00C57—C64—H64A109.00
C24—C23—H23120.00C57—C64—H64B109.00
C25—C24—H24120.00C57—C64—H64C109.00
C23—C24—H24120.00H64A—C64—H64B109.00
C26—C25—H25120.00H64A—C64—H64C110.00
C24—C25—H25120.00H64B—C64—H64C109.00
C25—C26—H26120.00C65—C66—H66119.00
C27—C26—H26120.00C67—C66—H66119.00
H28A—C28—H28C109.00C66—C67—H67120.00
C21—C28—H28A109.00C68—C67—H67120.00
H28A—C28—H28B109.00C67—C68—H68120.00
C21—C28—H28B109.00C69—C68—H68120.00
H28B—C28—H28C109.00C68—C69—H69120.00
C21—C28—H28C110.00C70—C69—H69120.00
C29—C30—H30119.00C71—C72—H72A109.00
C31—C30—H30119.00C71—C72—H72B109.00
C32—C31—H31121.00C71—C72—H72C109.00
C30—C31—H31121.00H72A—C72—H72B110.00
C33—C32—H32119.00H72A—C72—H72C110.00
C31—C32—H32119.00H72B—C72—H72C109.00
C9—N1—C1—C22.3 (8)C22—C23—C24—C251.8 (9)
C9—N1—C1—C11173.9 (5)C23—C24—C25—C260.9 (10)
C1—N1—C9—C42.0 (8)C24—C25—C26—C270.9 (9)
C1—N1—C9—C8177.4 (5)C25—C26—C27—N3179.1 (5)
C17—N2—C16—C11136.2 (6)C25—C26—C27—C221.9 (9)
C17—N2—C16—C1542.2 (8)C30—C29—C34—N4178.0 (5)
C16—N2—C17—O12.1 (10)C34—C29—C30—C313.1 (10)
C16—N2—C17—C18179.7 (6)C19—C29—C34—N46.1 (9)
C27—N3—C19—C200.4 (8)C30—C29—C34—C332.7 (8)
C27—N3—C19—C29175.4 (5)C19—C29—C34—C33173.2 (5)
C19—N3—C27—C220.2 (8)C19—C29—C30—C31172.9 (6)
C19—N3—C27—C26177.4 (5)C29—C30—C31—C321.9 (11)
C35—N4—C34—C3342.6 (8)C30—C31—C32—C330.2 (11)
C34—N4—C35—O21.0 (10)C31—C32—C33—C340.2 (10)
C35—N4—C34—C29136.7 (6)C32—C33—C34—N4179.6 (6)
C34—N4—C35—C36179.7 (6)C32—C33—C34—C291.1 (9)
C37—N5—C45—C44176.9 (5)C47—C37—C38—C39176.5 (5)
C37—N5—C45—C401.9 (8)N5—C37—C47—C48151.7 (6)
C45—N5—C37—C47174.4 (5)N5—C37—C38—C390.3 (8)
C45—N5—C37—C381.9 (7)C38—C37—C47—C52145.0 (6)
C53—N6—C52—C47135.1 (6)N5—C37—C47—C5231.3 (8)
C52—N6—C53—O33.6 (10)C38—C37—C47—C4832.0 (8)
C53—N6—C52—C5143.5 (9)C37—C38—C39—C402.4 (9)
C52—N6—C53—C54174.8 (6)C37—C38—C39—C46178.2 (5)
C55—N7—C63—C581.6 (8)C46—C39—C40—C45178.1 (6)
C55—N7—C63—C62177.6 (5)C38—C39—C40—C41177.8 (6)
C63—N7—C55—C65174.9 (5)C38—C39—C40—C452.3 (8)
C63—N7—C55—C561.9 (8)C46—C39—C40—C412.1 (9)
C70—N8—C71—C72175.2 (6)C45—C40—C41—C420.4 (9)
C71—N8—C70—C65135.5 (6)C39—C40—C45—N50.2 (8)
C70—N8—C71—O41.8 (10)C39—C40—C45—C44179.0 (5)
C71—N8—C70—C6942.6 (9)C41—C40—C45—N5179.9 (5)
C11—C1—C2—C3174.8 (5)C41—C40—C45—C441.1 (8)
N1—C1—C11—C12152.0 (6)C39—C40—C41—C42179.8 (6)
C2—C1—C11—C1231.8 (8)C40—C41—C42—C430.7 (10)
N1—C1—C11—C1631.9 (8)C41—C42—C43—C440.9 (10)
C2—C1—C11—C16144.3 (6)C42—C43—C44—C450.1 (9)
N1—C1—C2—C31.4 (9)C43—C44—C45—N5179.8 (5)
C1—C2—C3—C40.0 (8)C43—C44—C45—C400.9 (9)
C1—C2—C3—C10178.9 (6)C37—C47—C48—C49172.9 (6)
C10—C3—C4—C9179.2 (5)C52—C47—C48—C494.2 (10)
C2—C3—C4—C90.3 (8)C37—C47—C52—N65.1 (8)
C10—C3—C4—C51.6 (9)C48—C47—C52—N6177.8 (5)
C2—C3—C4—C5177.3 (5)C48—C47—C52—C513.6 (8)
C3—C4—C9—C8178.7 (5)C37—C47—C52—C51173.5 (5)
C5—C4—C9—N1178.4 (5)C47—C48—C49—C502.3 (11)
C9—C4—C5—C60.7 (8)C48—C49—C50—C510.4 (10)
C5—C4—C9—C81.0 (8)C49—C50—C51—C520.9 (10)
C3—C4—C9—N10.7 (8)C50—C51—C52—N6179.8 (6)
C3—C4—C5—C6178.3 (6)C50—C51—C52—C471.2 (9)
C4—C5—C6—C70.4 (9)N7—C55—C56—C571.0 (9)
C5—C6—C7—C81.1 (10)C65—C55—C56—C57175.7 (5)
C6—C7—C8—C90.8 (10)N7—C55—C65—C66151.4 (5)
C7—C8—C9—C40.2 (9)N7—C55—C65—C7032.0 (7)
C7—C8—C9—N1179.2 (6)C56—C55—C65—C6631.7 (7)
C12—C11—C16—N2178.4 (5)C56—C55—C65—C70144.9 (5)
C16—C11—C12—C132.9 (9)C55—C56—C57—C580.3 (9)
C1—C11—C16—C15173.0 (5)C55—C56—C57—C64178.5 (6)
C1—C11—C16—N25.4 (8)C56—C57—C58—C59178.5 (6)
C12—C11—C16—C153.3 (8)C56—C57—C58—C630.7 (8)
C1—C11—C12—C13173.5 (6)C64—C57—C58—C590.3 (9)
C11—C12—C13—C141.2 (10)C64—C57—C58—C63178.9 (5)
C12—C13—C14—C150.2 (10)C57—C58—C59—C60179.1 (6)
C13—C14—C15—C160.2 (10)C63—C58—C59—C600.0 (9)
C14—C15—C16—C112.0 (9)C57—C58—C63—N70.3 (8)
C14—C15—C16—N2179.6 (6)C57—C58—C63—C62178.9 (5)
N3—C19—C20—C211.2 (9)C59—C58—C63—N7179.5 (5)
C29—C19—C20—C21176.2 (5)C59—C58—C63—C620.3 (8)
C20—C19—C29—C34142.6 (6)C58—C59—C60—C610.2 (10)
C20—C19—C29—C3033.1 (8)C59—C60—C61—C620.0 (9)
N3—C19—C29—C30151.7 (6)C60—C61—C62—C630.3 (9)
N3—C19—C29—C3432.5 (8)C61—C62—C63—N7179.7 (5)
C19—C20—C21—C221.7 (9)C61—C62—C63—C580.5 (9)
C19—C20—C21—C28179.2 (6)C55—C65—C66—C67173.5 (6)
C28—C21—C22—C27179.0 (6)C70—C65—C66—C673.3 (9)
C28—C21—C22—C230.2 (9)C55—C65—C70—N84.7 (8)
C20—C21—C22—C23177.3 (6)C55—C65—C70—C69173.5 (5)
C20—C21—C22—C271.5 (8)C66—C65—C70—N8178.7 (5)
C21—C22—C23—C24179.6 (6)C66—C65—C70—C693.2 (8)
C21—C22—C27—C26177.8 (5)C65—C66—C67—C681.4 (10)
C27—C22—C23—C240.9 (9)C66—C67—C68—C690.7 (10)
C21—C22—C27—N30.7 (8)C67—C68—C69—C700.8 (10)
C23—C22—C27—C261.0 (9)C68—C69—C70—N8179.4 (6)
C23—C22—C27—N3178.1 (5)C68—C69—C70—C651.2 (9)
Symmetry codes: (i) x1, y1, z; (ii) x, y+1, z; (iii) x1, y, z; (iv) x, y1, z; (v) x1, y+1, z; (vi) x+1, y, z; (vii) x+1, y+1, z; (viii) x+1, y1, z; (ix) x, y1, z1; (x) x, y, z+1; (xi) x, y+1, z+1; (xii) x1, y, z1; (xiii) x, y, z1; (xiv) x+1, y, z+1.
Hydrogen-bond geometry (Å, º) top
Cg3, Cg7, Cg11, Cg15 are the centroids of the C11–C16, C29–C34, C47–C52 and C65–C70 rings, respectively.
D—H···AD—HH···AD···AD—H···A
N2—H2N···O4vi0.862.423.181 (6)148
N2—H2N···N10.862.252.741 (7)117
N4—H4N···O3iv0.862.393.160 (6)149
N4—H4N···N30.862.252.735 (7)116
N6—H6N···O2vii0.862.513.262 (6)147
N6—H6N···N50.862.212.703 (7)116
N8—H8N···O10.862.493.239 (6)146
N8—H8N···N70.862.202.705 (7)118
C15—H15···O10.932.512.905 (7)106
C33—H33···O20.932.512.894 (7)105
C36—H36B···O3iv0.962.313.201 (7)154
C44—H44···O2vii0.932.603.472 (9)157
C51—H51···O30.932.532.927 (7)106
C54—H54B···O2vii0.962.283.213 (8)162
C69—H69···O40.932.522.911 (7)106
C10—H10A···Cg15viii0.962.763.586 (7)145
C28—H28B···Cg110.962.633.579 (7)171
C46—H46C···Cg7vi0.962.653.594 (7)168
C64—H64C···Cg3ii0.962.653.604 (7)173
Symmetry codes: (ii) x, y+1, z; (iv) x, y1, z; (vi) x+1, y, z; (vii) x+1, y+1, z; (viii) x+1, y1, z.

Experimental details

Crystal data
Chemical formulaC18H16N2O
Mr276.33
Crystal system, space groupTriclinic, P1
Temperature (K)295
a, b, c (Å)9.7383 (5), 9.9035 (6), 15.2809 (9)
α, β, γ (°)101.414 (5), 99.188 (5), 90.065 (5)
V3)1425.24 (14)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.20 × 0.10 × 0.10
Data collection
DiffractometerOxford Xcalibur Eos(Nova) CCD detector
Absorption correctionMulti-scan
(CrysAlis PRO RED; Oxford Diffraction, 2009)
Tmin, Tmax0.984, 0.992
No. of measured, independent and
observed [I > 2σ(I)] reflections
29328, 5290, 3314
Rint0.079
(sin θ/λ)max1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.058, 0.164, 0.94
No. of reflections5290
No. of parameters766
No. of restraints3
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.23, 0.24

Computer programs: CrysAlis PRO CCD (Oxford Diffraction, 2009), CrysAlis PRO RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top
Cg3, Cg7, Cg11, Cg15 are the centroids of the C11–C16, C29–C34, C47–C52 and C65–C70 rings, respectively.
D—H···AD—HH···AD···AD—H···A
N2—H2N···O4i0.862.423.181 (6)148
N2—H2N···N10.862.252.741 (7)117
N4—H4N···O3ii0.862.393.160 (6)149
N4—H4N···N30.862.252.735 (7)116
N6—H6N···O2iii0.862.513.262 (6)147
N6—H6N···N50.862.212.703 (7)116
N8—H8N···O10.862.493.239 (6)146
N8—H8N···N70.862.202.705 (7)118
C36—H36B···O3ii0.962.313.201 (7)154
C44—H44···O2iii0.932.603.472 (9)157
C54—H54B···O2iii0.962.283.213 (8)162
C10—H10A···Cg15iv0.962.763.586 (7)145
C28—H28B···Cg110.962.633.579 (7)171
C46—H46C···Cg7i0.962.653.594 (7)168
C64—H64C···Cg3v0.962.653.604 (7)173
Symmetry codes: (i) x+1, y, z; (ii) x, y1, z; (iii) x+1, y+1, z; (iv) x+1, y1, z; (v) x, y+1, z.
 

Acknowledgements

We thank the DDepartment of Science and Technology (DST), India, and Professor T. N. Guru Row, IISc, Bangalore, for use of the CCD facility set up under the IRHPA–DST program at IISc. FNK thanks the DST for Fast Track Proposal funding.

References

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