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Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890
Volume 65| Part 1| January 2009| Pages o66-o67

4-[(5-Hydr­­oxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)phenyl­meth­yl]-5-methyl-2-phenyl-1H-pyrazol-3(2H)-one ethanol hemisolvate

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 19 November 2008; accepted 21 November 2008; online 10 December 2008)

The asymmetric unit of the title compound, C27H24N4O2·0.5C2H6O, comprises two crystallographically independent mol­ecules (A and B) with slightly different conformations, and one ethanol mol­ecule of crystallization. Intra­molecular C—H⋯O and O—H⋯O hydrogen bonds generate six- and eight-membered rings, producing S(6) and S(8) ring motifs, respectively. In mol­ecule A, one of the benzene rings is disordered over two positions, with site-occupancy factors of 0.542 (11) and 0.458 (11). The dihedral angles between the central benzene ring and the two outer benzene rings are 73.88 (9) and 82.6 (2)/88.9 (2)° in mol­ecule A, and 80.81 (8) and 79.38 (8)° in mol­ecule B. In the crystal structure, mol­ecules form infinite one-dimensional chains in the (101) plane. The crystal structure is stabilized by inter­molecular O—H⋯N, N—H⋯N, N—H⋯O and C—H⋯O hydrogen bonds, weak C—H⋯π and ππ [centroid–centroid = 3.5496 (1) Å] inter­actions.

Related literature

For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). 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.]). For details of the biological activity of pyrazole derivatives, see: Burger & Iorio (1979[Burger, J. C. & Iorio, L. C. (1979). Annu. Rep. Med. Chem. 14, 27-64.], 1980[Burger, J. C. & Iorio, L. C. (1980). Annu. Rep. Med. Chem. 15, 26-50.]); Kalluraya & Ramesh (2001[Kalluraya, B. & Ramesh, M. C. (2001). Indian J. Heterocycl. Chem. 11, 171-175.]); Holla et al. (1994[Holla, B. S., Kalluraya, B., Sridhar, K., Erick, P., Thomas, L. & Bhandary, K. K. (1994). Eur. J. Med. Chem. 29, 301-307.]); Windholz (2003[Windholz, M. (2003). The Merck Index, 9th ed. Rahaway, New Jersey: Merck & Co.]).

[Scheme 1]

Experimental

Crystal data
  • C27H24N4O2·0.5C2H6O

  • Mr = 459.54

  • Triclinic, [P \overline 1]

  • a = 8.3767 (2) Å

  • b = 13.9498 (3) Å

  • c = 20.4797 (4) Å

  • α = 101.074 (1)°

  • β = 93.723 (1)°

  • γ = 93.579 (1)°

  • V = 2336.74 (9) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 100.0 (1) K

  • 0.38 × 0.26 × 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 = 0.960, Tmax = 0.986

  • 41677 measured reflections

  • 13462 independent reflections

  • 9482 reflections with I > 2σ(I)

  • Rint = 0.043

Refinement
  • R[F2 > 2σ(F2)] = 0.055

  • wR(F2) = 0.161

  • S = 1.03

  • 13462 reflections

  • 632 parameters

  • 42 restraints

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

  • Δρmax = 0.40 e Å−3

  • Δρmin = −0.43 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O2A—H2OA⋯O1A 0.82 1.76 2.5755 (16) 173
O3—H3⋯N3Ai 0.82 2.11 2.923 (2) 173
O2B—H2OB⋯O1B 0.82 1.68 2.4970 (16) 176
N2A—H2NA⋯N3Bii 0.93 (3) 1.88 (3) 2.810 (2) 176 (2)
N2B—H2NB⋯O1Aiii 0.95 (2) 1.75 (2) 2.6922 (19) 173 (2)
C1B—H1BA⋯O1B 0.93 2.37 2.925 (2) 118
C2B—H2BA⋯O3iv 0.93 2.48 3.313 (2) 149
C21A—H21A⋯O2A 0.93 2.41 2.910 (5) 114
C5B—H5BACg1i 0.93 2.89 3.595 (3) 134
C29—H29BCg2iv 0.97 2.80 3.492 (2) 129
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+1, -y+1, -z; (iii) x+1, y+1, z; (iv) x+1, y, z. Cg1 and Cg2 are the centroids of the C11A–C16A and C20C–C25C benzene rings, respectively.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); 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

Pyrazole derivatives are reported to possess varied biological activities such as anti-inflammatory (Windholz 2003), analgesic (Windholz 2003), hypoglysemic, seditive (Burger et al., 1979), hypnotic (Burger et al., 1980), antifungal and antibacterial (Kalluraya et al., 2001) activities. Propenones are also found to show good antibacterial activity (Holla et al. 1994). Prompted by these observations, we planned to synthesize propenones containing pyrazole moiety and we report here the structure of the title compound, I, Fig. 1.

The bond lengths (Allen et al., 1987) and angles in the title compound have normal values. The asymmetric unit of the title compound, is composed of two crystallographically independent molecules (A and B) with slightly different conformations and one ethanol molecule of crystallization. Intramolecular C—H···O and O—H···O hydrogen bonds generate six- and eight-membered rings, producing S(6) and S(8) ring motifs (Bernstein et al. 1995), respectively. In molecule A, one of the benzene rings is disordered over two positions with the site-occupancy factors 0.542 (11)/0.458 (11). The dihedral angles between the central benzene ring and the two outer benzene rings are 73.88 (9) and 82.6 (2)/88.9 (2)° in molecule A; and 80.81 (8) and 79.38 (8)° in molecule B, respectively. In the crystal structure, molecules are linked into infinite 1-dimensional chains in the (101)-plane (Fig. 2). The crystal structure is stabilized by intermolecular O—H···N, N—H···N, N—H···O, and C—H···O hydrogen bonds, weak C—H···π (Table 1, Cg1 and Cg2 are the centroids of the C11A–C16A and C20C–C25C benzene rings respectively) and π-π interactions [Cg3···Cg4 = 3.5496 (10) Å; symmetry code: -1 + x,-1 + y, z; Cg3 and Cg4 are the centroids of the C1A–C6A and N1B/N2B/C7B–C9B benzene rings respectively].

Related literature top

For hydrogen-bond motifs, see: Bernstein et al. (1995). For bond-length data, see: Allen et al. (1987). For details of the biological activity of pyrazole derivatives, see: Burger & Iorio (1979, 1980); Kalluraya & Ramesh (2001); Holla et al. (1994); Windholz (2003). Cg1 and Cg2 are the centroids of the C11A–C16A and C20C–C25C benzene rings, respectively.

Experimental top

The title compound was prepared by the direct fusion of 1-phenyl- 3-methyl 5-pyrazolone (0.1 mole) with benzaldehyde (0.1 mole) at 413 K for 3 h. The reaction mixture was cooled to room temperature and stirred with methanol using a glass rod. The mixture was then filtered to obtain a solid product. Single crystals suitable for X-ray analysis were obtained by recrystallization from ethanol under slow evaporation (m.p. 351–353 K).

Refinement top

N-bonded H atoms were located from the difference Fourier map and freely refined. H atoms of the hydroxy groups were positioned with freely rotating O—H bonds and constrained with a fixed distance of 0.82 Å. Other hydrogen atoms were positioned geometrically and refined using a riding model with C—H = 0.93–0.98 Å and Uiso(H) = 1.2 or 1.5 Ueq(C). A rotating-group model was applied to the methyl hydrogen atoms. One of the benzene rings in molecule A is disordered over two positions with site-occupancy factors 0.542 (11)/0.458 (11). The disorder was modeled based on a rigid bond model and the C atoms refined isotropically.

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 (I) with atom labels and 40% probability ellipsoids for non-H atoms. For clarity, only the hydrogen atoms involved in the hydrogen bonding and the hydrogen of the ethanol molecule are shown. Intramolecular interactions are shown as dashed lines. The solid bonds show the major disorder component.
[Figure 2] Fig. 2. The crystal packing of the major disorder component of (I), showing the infinite 1-dimensional chains along (1 0 1). Intermolecular interactions are shown as dashed lines.
4-[(5-Hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)phenylmethyl]-5-methyl-2-phenyl-1H-pyrazol-3(2H)-one ethanol hemisolvate top
Crystal data top
C27H24N4O2·0.5C2H6OZ = 4
Mr = 459.54F(000) = 972
Triclinic, P1Dx = 1.306 Mg m3
Hall symbol: -P 1Melting point: 352 K
a = 8.3767 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 13.9498 (3) ÅCell parameters from 8872 reflections
c = 20.4797 (4) Åθ = 2.5–31.5°
α = 101.074 (1)°µ = 0.09 mm1
β = 93.723 (1)°T = 100 K
γ = 93.579 (1)°Block, yellow
V = 2336.74 (9) Å30.38 × 0.26 × 0.17 mm
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
13462 independent reflections
Radiation source: fine-focus sealed tube9482 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.043
ϕ and ω scansθmax = 30.0°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
h = 1111
Tmin = 0.960, Tmax = 0.986k = 1919
41677 measured reflectionsl = 2628
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)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.161H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0833P)2 + 0.5342P]
where P = (Fo2 + 2Fc2)/3
13462 reflections(Δ/σ)max < 0.001
632 parametersΔρmax = 0.40 e Å3
42 restraintsΔρmin = 0.43 e Å3
Crystal data top
C27H24N4O2·0.5C2H6Oγ = 93.579 (1)°
Mr = 459.54V = 2336.74 (9) Å3
Triclinic, P1Z = 4
a = 8.3767 (2) ÅMo Kα radiation
b = 13.9498 (3) ŵ = 0.09 mm1
c = 20.4797 (4) ÅT = 100 K
α = 101.074 (1)°0.38 × 0.26 × 0.17 mm
β = 93.723 (1)°
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
13462 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
9482 reflections with I > 2σ(I)
Tmin = 0.960, Tmax = 0.986Rint = 0.043
41677 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.05542 restraints
wR(F2) = 0.161H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.40 e Å3
13462 reflectionsΔρmin = 0.43 e Å3
632 parameters
Special details top

Experimental. The low-temperature 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*/UeqOcc. (<1)
O1A0.04693 (14)0.06678 (8)0.31199 (5)0.0191 (2)
O2A0.06851 (15)0.10931 (9)0.44047 (6)0.0228 (3)
H2OA0.05340.09420.39970.034*
N1A0.15609 (16)0.11331 (10)0.22035 (6)0.0160 (3)
N2A0.21144 (16)0.20043 (10)0.20320 (7)0.0164 (3)
N3A0.30731 (16)0.31761 (10)0.52500 (7)0.0186 (3)
N4A0.24860 (16)0.22036 (10)0.51385 (7)0.0173 (3)
C20A0.3120 (10)0.1609 (6)0.5553 (5)0.021 (2)*0.542 (11)
C21A0.3284 (6)0.0608 (3)0.5268 (2)0.0232 (10)*0.542 (11)
H21A0.29840.03690.48180.028*0.542 (11)
C22A0.3892 (7)0.0009 (3)0.5663 (2)0.0322 (11)*0.542 (11)
H22A0.39340.06700.54800.039*0.542 (11)
C23A0.4433 (7)0.0336 (4)0.6317 (3)0.0304 (13)*0.542 (11)
H23A0.47790.00890.65860.036*0.542 (11)
C24A0.4451 (8)0.1300 (4)0.6562 (3)0.0352 (16)*0.542 (11)
H24A0.48840.15520.69950.042*0.542 (11)
C25A0.3826 (7)0.1931 (4)0.6171 (3)0.0305 (16)*0.542 (11)
H25A0.39030.26000.63470.037*0.542 (11)
C20C0.3025 (11)0.1530 (7)0.5557 (5)0.016 (2)*0.458 (11)
C21C0.2784 (8)0.0544 (4)0.5377 (3)0.0301 (13)*0.458 (11)
H21C0.22260.02620.49710.036*0.458 (11)
C22C0.3367 (8)0.0048 (3)0.5795 (3)0.0282 (13)*0.458 (11)
H22C0.32350.07260.56630.034*0.458 (11)
C23C0.4148 (7)0.0373 (4)0.6411 (3)0.0186 (11)*0.458 (11)
H23C0.46370.00130.66760.022*0.458 (11)
C24C0.4187 (7)0.1381 (4)0.6624 (3)0.0146 (11)*0.458 (11)
H24C0.46450.16600.70490.018*0.458 (11)
C25C0.3572 (7)0.1980 (4)0.6228 (3)0.0134 (12)*0.458 (11)
H25C0.35140.26460.63870.016*0.458 (11)
C1A0.25204 (19)0.05002 (12)0.20784 (9)0.0205 (3)
H1AA0.29100.03620.25250.025*
C2A0.2680 (2)0.14120 (13)0.16831 (10)0.0252 (4)
H2AA0.31770.18860.18680.030*
C3A0.2111 (2)0.16232 (13)0.10179 (9)0.0247 (4)
H3AA0.22250.22350.07570.030*
C4A0.1370 (2)0.09156 (13)0.07439 (9)0.0259 (4)
H4AA0.09920.10530.02960.031*
C5A0.1188 (2)0.00035 (13)0.11323 (8)0.0218 (3)
H5AA0.06790.04670.09480.026*
C6A0.17717 (18)0.02021 (12)0.17991 (8)0.0159 (3)
C7A0.09891 (18)0.13337 (12)0.28245 (7)0.0150 (3)
C8A0.11043 (17)0.23705 (11)0.30291 (7)0.0142 (3)
C9A0.17638 (18)0.27454 (12)0.25245 (8)0.0156 (3)
C10A0.04788 (18)0.29225 (12)0.36615 (7)0.0147 (3)
H10A0.06380.36190.36430.018*
C11A0.13429 (18)0.27032 (11)0.36632 (8)0.0150 (3)
C12A0.23042 (19)0.24023 (13)0.30674 (8)0.0200 (3)
H12A0.18300.23030.26640.024*
C13A0.3961 (2)0.22486 (14)0.30669 (9)0.0242 (4)
H13A0.45830.20410.26660.029*
C14A0.4685 (2)0.24037 (14)0.36616 (9)0.0253 (4)
H14A0.57920.23010.36630.030*
C15A0.3747 (2)0.27133 (15)0.42537 (9)0.0258 (4)
H15A0.42310.28270.46540.031*
C16A0.2086 (2)0.28570 (13)0.42591 (8)0.0209 (3)
H16A0.14710.30570.46630.025*
C17A0.14073 (18)0.28029 (12)0.42951 (7)0.0153 (3)
C18A0.24186 (18)0.35227 (12)0.47389 (8)0.0170 (3)
C19A0.14672 (19)0.19775 (12)0.45748 (8)0.0168 (3)
C26A0.2124 (2)0.37793 (13)0.24580 (9)0.0249 (4)
H26A0.27910.37950.20960.037*
H26B0.26730.41430.28650.037*
H26C0.11400.40670.23710.037*
C27A0.2781 (2)0.45637 (13)0.46862 (9)0.0262 (4)
H27A0.33840.49080.50860.039*
H27B0.17950.48650.46290.039*
H27C0.33970.45880.43100.039*
O2B0.93942 (14)0.63369 (8)0.04138 (6)0.0179 (2)
H2OB0.92720.64400.08150.027*
O1B0.91354 (13)0.66225 (8)0.16426 (5)0.0182 (2)
N4B0.90424 (15)0.71344 (10)0.04759 (6)0.0150 (3)
N3B0.81223 (16)0.78239 (10)0.06849 (7)0.0170 (3)
N2B0.88285 (17)0.89755 (11)0.25148 (7)0.0190 (3)
N1B0.94837 (16)0.80809 (10)0.24321 (7)0.0173 (3)
C1B1.1437 (2)0.70528 (14)0.28164 (9)0.0243 (4)
H1BA1.14680.67100.23810.029*
C2B1.2358 (2)0.68007 (16)0.33339 (9)0.0314 (4)
H2BA1.30020.62780.32470.038*
C3B1.2329 (2)0.73225 (17)0.39840 (9)0.0339 (5)
H3BA1.29540.71490.43290.041*
C4B1.1377 (2)0.80951 (16)0.41180 (9)0.0306 (4)
H4BA1.13670.84440.45530.037*
C5B1.0431 (2)0.83566 (14)0.36065 (8)0.0233 (4)
H5BA0.97850.88770.36960.028*
C6B1.04641 (19)0.78271 (13)0.29578 (8)0.0196 (3)
C7B0.87984 (18)0.74959 (12)0.18494 (8)0.0157 (3)
C8B0.76814 (18)0.80655 (11)0.15665 (7)0.0147 (3)
C9B0.77990 (19)0.89732 (12)0.19769 (8)0.0172 (3)
C10B0.65481 (18)0.76875 (11)0.09613 (7)0.0142 (3)
H10B0.58280.82090.09360.017*
C11B0.54597 (17)0.67919 (11)0.10342 (8)0.0137 (3)
C12B0.45406 (19)0.62474 (12)0.04803 (8)0.0186 (3)
H12B0.46460.64040.00630.022*
C13B0.3471 (2)0.54760 (13)0.05414 (9)0.0227 (3)
H13B0.28580.51250.01670.027*
C14B0.3314 (2)0.52257 (13)0.11590 (9)0.0217 (3)
H14B0.26030.47040.11990.026*
C15B0.42219 (19)0.57569 (12)0.17175 (8)0.0190 (3)
H15B0.41230.55910.21320.023*
C16B0.52806 (18)0.65393 (12)0.16558 (8)0.0163 (3)
H16B0.58760.68980.20320.020*
C17B0.73824 (18)0.75532 (11)0.03188 (8)0.0142 (3)
C18B0.71295 (19)0.80612 (12)0.02041 (8)0.0160 (3)
C19B0.86207 (18)0.69663 (11)0.01323 (7)0.0140 (3)
C20B1.04430 (18)0.68613 (12)0.08021 (7)0.0154 (3)
C21B1.09192 (19)0.59116 (12)0.08653 (8)0.0183 (3)
H21B1.03160.54410.07010.022*
C22B1.2306 (2)0.56752 (13)0.11770 (8)0.0216 (3)
H22B1.26330.50430.12200.026*
C23B1.3209 (2)0.63729 (13)0.14245 (8)0.0221 (3)
H23B1.41390.62080.16310.027*
C24B1.2724 (2)0.73159 (13)0.13640 (8)0.0211 (3)
H24B1.33270.77830.15310.025*
C25B1.13422 (19)0.75638 (12)0.10552 (8)0.0190 (3)
H25B1.10150.81960.10170.023*
C26B0.7042 (2)0.98896 (12)0.19062 (9)0.0231 (4)
H26D0.70491.03100.23370.035*
H26E0.59550.97300.17190.035*
H26F0.76331.02190.16170.035*
C27B0.5924 (2)0.87954 (13)0.02620 (9)0.0232 (4)
H27D0.59400.89720.06920.035*
H27E0.61850.93690.00800.035*
H27F0.48730.85160.02110.035*
C280.8096 (3)0.54578 (19)0.31209 (13)0.0480 (6)
H28A0.88870.50140.29700.072*
H28B0.85530.59380.34980.072*
H28C0.77540.57800.27680.072*
C290.6683 (3)0.48982 (15)0.33204 (10)0.0331 (4)
H29A0.62450.44040.29400.040*
H29B0.70430.45630.36700.040*
O30.54565 (15)0.54997 (10)0.35503 (7)0.0291 (3)
H30.58030.58970.38860.044*
H2NA0.208 (3)0.2048 (18)0.1585 (13)0.048 (7)*
H2NB0.944 (3)0.9543 (17)0.2753 (11)0.035 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0252 (6)0.0155 (6)0.0156 (5)0.0042 (5)0.0035 (5)0.0021 (4)
O2A0.0316 (7)0.0195 (6)0.0155 (5)0.0062 (5)0.0026 (5)0.0028 (5)
N1A0.0195 (6)0.0140 (6)0.0144 (6)0.0000 (5)0.0034 (5)0.0020 (5)
N2A0.0203 (6)0.0152 (7)0.0145 (6)0.0016 (5)0.0046 (5)0.0035 (5)
N3A0.0175 (6)0.0184 (7)0.0180 (6)0.0009 (5)0.0008 (5)0.0005 (5)
N4A0.0181 (6)0.0175 (7)0.0152 (6)0.0011 (5)0.0005 (5)0.0011 (5)
C1A0.0178 (7)0.0225 (9)0.0215 (8)0.0052 (7)0.0031 (6)0.0037 (7)
C2A0.0239 (8)0.0207 (9)0.0336 (10)0.0092 (7)0.0087 (7)0.0073 (7)
C3A0.0228 (8)0.0182 (9)0.0319 (9)0.0005 (7)0.0112 (7)0.0011 (7)
C4A0.0301 (9)0.0243 (9)0.0203 (8)0.0011 (8)0.0024 (7)0.0029 (7)
C5A0.0259 (8)0.0190 (8)0.0202 (8)0.0044 (7)0.0007 (7)0.0028 (7)
C6A0.0150 (7)0.0153 (8)0.0169 (7)0.0017 (6)0.0044 (6)0.0005 (6)
C7A0.0125 (6)0.0186 (8)0.0132 (7)0.0001 (6)0.0007 (5)0.0015 (6)
C8A0.0116 (6)0.0163 (8)0.0140 (7)0.0004 (6)0.0008 (5)0.0018 (6)
C9A0.0145 (7)0.0175 (8)0.0146 (7)0.0018 (6)0.0004 (6)0.0024 (6)
C10A0.0149 (7)0.0146 (7)0.0140 (7)0.0003 (6)0.0023 (6)0.0012 (6)
C11A0.0140 (7)0.0150 (7)0.0163 (7)0.0032 (6)0.0013 (6)0.0029 (6)
C12A0.0173 (7)0.0241 (9)0.0172 (7)0.0036 (7)0.0013 (6)0.0001 (6)
C13A0.0159 (7)0.0292 (10)0.0252 (9)0.0031 (7)0.0030 (7)0.0004 (7)
C14A0.0134 (7)0.0343 (10)0.0304 (9)0.0041 (7)0.0031 (7)0.0103 (8)
C15A0.0172 (8)0.0416 (11)0.0222 (8)0.0082 (8)0.0068 (7)0.0119 (8)
C16A0.0177 (7)0.0298 (9)0.0164 (7)0.0057 (7)0.0024 (6)0.0057 (7)
C17A0.0143 (7)0.0178 (8)0.0127 (7)0.0009 (6)0.0023 (6)0.0003 (6)
C18A0.0144 (7)0.0197 (8)0.0152 (7)0.0006 (6)0.0011 (6)0.0008 (6)
C19A0.0175 (7)0.0182 (8)0.0132 (7)0.0004 (6)0.0017 (6)0.0002 (6)
C26A0.0349 (10)0.0205 (9)0.0203 (8)0.0006 (7)0.0078 (7)0.0051 (7)
C27A0.0297 (9)0.0231 (9)0.0232 (8)0.0042 (7)0.0053 (7)0.0024 (7)
O2B0.0235 (6)0.0172 (6)0.0145 (5)0.0064 (5)0.0033 (5)0.0046 (4)
O1B0.0213 (6)0.0160 (6)0.0165 (5)0.0032 (5)0.0001 (4)0.0013 (4)
N4B0.0165 (6)0.0145 (6)0.0146 (6)0.0041 (5)0.0031 (5)0.0030 (5)
N3B0.0188 (6)0.0170 (7)0.0163 (6)0.0050 (5)0.0023 (5)0.0048 (5)
N2B0.0200 (7)0.0140 (7)0.0202 (7)0.0016 (5)0.0006 (6)0.0026 (5)
N1B0.0176 (6)0.0163 (7)0.0160 (6)0.0006 (5)0.0005 (5)0.0008 (5)
C1B0.0206 (8)0.0336 (10)0.0181 (8)0.0023 (7)0.0009 (6)0.0038 (7)
C2B0.0243 (9)0.0463 (12)0.0251 (9)0.0097 (9)0.0001 (7)0.0089 (9)
C3B0.0262 (9)0.0558 (14)0.0207 (9)0.0038 (9)0.0029 (7)0.0116 (9)
C4B0.0295 (9)0.0453 (12)0.0144 (8)0.0051 (9)0.0007 (7)0.0020 (8)
C5B0.0227 (8)0.0281 (9)0.0172 (8)0.0033 (7)0.0026 (7)0.0010 (7)
C6B0.0158 (7)0.0265 (9)0.0158 (7)0.0043 (6)0.0001 (6)0.0049 (7)
C7B0.0163 (7)0.0164 (8)0.0133 (7)0.0023 (6)0.0025 (6)0.0005 (6)
C8B0.0157 (7)0.0147 (7)0.0130 (7)0.0008 (6)0.0027 (6)0.0009 (6)
C9B0.0157 (7)0.0177 (8)0.0176 (7)0.0009 (6)0.0050 (6)0.0018 (6)
C10B0.0147 (7)0.0141 (7)0.0139 (7)0.0022 (6)0.0024 (6)0.0016 (6)
C11B0.0116 (6)0.0128 (7)0.0164 (7)0.0023 (6)0.0025 (5)0.0010 (6)
C12B0.0198 (7)0.0189 (8)0.0165 (7)0.0008 (6)0.0003 (6)0.0037 (6)
C13B0.0201 (8)0.0226 (9)0.0231 (8)0.0047 (7)0.0045 (7)0.0026 (7)
C14B0.0176 (7)0.0195 (9)0.0282 (9)0.0039 (6)0.0003 (7)0.0072 (7)
C15B0.0184 (7)0.0205 (8)0.0190 (8)0.0022 (6)0.0042 (6)0.0053 (6)
C16B0.0160 (7)0.0168 (8)0.0154 (7)0.0021 (6)0.0020 (6)0.0010 (6)
C17B0.0134 (6)0.0131 (7)0.0158 (7)0.0002 (6)0.0008 (6)0.0025 (6)
C18B0.0165 (7)0.0151 (8)0.0160 (7)0.0007 (6)0.0007 (6)0.0025 (6)
C19B0.0153 (7)0.0124 (7)0.0134 (7)0.0011 (6)0.0011 (6)0.0009 (6)
C20B0.0157 (7)0.0177 (8)0.0120 (7)0.0021 (6)0.0006 (6)0.0009 (6)
C21B0.0193 (7)0.0160 (8)0.0185 (7)0.0009 (6)0.0015 (6)0.0006 (6)
C22B0.0212 (8)0.0220 (9)0.0220 (8)0.0075 (7)0.0036 (7)0.0024 (7)
C23B0.0190 (8)0.0286 (9)0.0186 (8)0.0050 (7)0.0036 (6)0.0024 (7)
C24B0.0192 (8)0.0255 (9)0.0197 (8)0.0007 (7)0.0032 (6)0.0072 (7)
C25B0.0199 (7)0.0174 (8)0.0198 (8)0.0026 (6)0.0017 (6)0.0036 (6)
C26B0.0252 (8)0.0162 (8)0.0262 (9)0.0015 (7)0.0026 (7)0.0006 (7)
C27B0.0229 (8)0.0281 (9)0.0216 (8)0.0107 (7)0.0034 (7)0.0088 (7)
C280.0409 (12)0.0560 (16)0.0466 (13)0.0062 (11)0.0164 (11)0.0035 (12)
C290.0431 (11)0.0272 (10)0.0292 (10)0.0105 (9)0.0053 (9)0.0025 (8)
O30.0254 (6)0.0281 (7)0.0295 (7)0.0029 (6)0.0028 (5)0.0038 (6)
Geometric parameters (Å, º) top
O1A—C7A1.2720 (19)C27A—H27B0.9600
O2A—C19A1.333 (2)C27A—H27C0.9600
O2A—H2OA0.8200O2B—C19B1.3191 (18)
N1A—C7A1.3727 (19)O2B—H2OB0.8200
N1A—N2A1.3892 (18)O1B—C7B1.2664 (19)
N1A—C6A1.428 (2)N4B—C19B1.3749 (19)
N2A—C9A1.359 (2)N4B—N3B1.3821 (17)
N2A—H2NA0.93 (3)N4B—C20B1.4240 (19)
N3A—C18A1.335 (2)N3B—C18B1.3366 (19)
N3A—N4A1.3848 (19)N2B—C9B1.354 (2)
N4A—C19A1.363 (2)N2B—N1B1.3798 (19)
N4A—C20A1.400 (9)N2B—H2NB0.95 (2)
N4A—C20C1.461 (10)N1B—C7B1.378 (2)
C20A—C25A1.344 (11)N1B—C6B1.424 (2)
C20A—C21A1.424 (9)C1B—C2B1.383 (2)
C21A—C22A1.386 (5)C1B—C6B1.391 (2)
C21A—H21A0.9300C1B—H1BA0.9300
C22A—C23A1.371 (6)C2B—C3B1.392 (3)
C22A—H22A0.9300C2B—H2BA0.9300
C23A—C24A1.339 (8)C3B—C4B1.376 (3)
C23A—H23A0.9300C3B—H3BA0.9300
C24A—C25A1.401 (8)C4B—C5B1.391 (3)
C24A—H24A0.9300C4B—H4BA0.9300
C25A—H25A0.9300C5B—C6B1.394 (2)
C20C—C21C1.353 (10)C5B—H5BA0.9300
C20C—C25C1.428 (11)C7B—C8B1.429 (2)
C21C—C22C1.386 (6)C8B—C9B1.373 (2)
C21C—H21C0.9300C8B—C10B1.500 (2)
C22C—C23C1.387 (7)C9B—C26B1.489 (2)
C22C—H22C0.9300C10B—C17B1.515 (2)
C23C—C24C1.388 (7)C10B—C11B1.537 (2)
C23C—H23C0.9300C10B—H10B0.9800
C24C—C25C1.372 (7)C11B—C12B1.392 (2)
C24C—H24C0.9300C11B—C16B1.399 (2)
C25C—H25C0.9300C12B—C13B1.386 (2)
C1A—C6A1.388 (2)C12B—H12B0.9300
C1A—C2A1.390 (2)C13B—C14B1.387 (2)
C1A—H1AA0.9300C13B—H13B0.9300
C2A—C3A1.384 (3)C14B—C15B1.388 (2)
C2A—H2AA0.9300C14B—H14B0.9300
C3A—C4A1.385 (3)C15B—C16B1.393 (2)
C3A—H3AA0.9300C15B—H15B0.9300
C4A—C5A1.388 (2)C16B—H16B0.9300
C4A—H4AA0.9300C17B—C19B1.389 (2)
C5A—C6A1.390 (2)C17B—C18B1.405 (2)
C5A—H5AA0.9300C18B—C27B1.498 (2)
C7A—C8A1.422 (2)C20B—C21B1.392 (2)
C8A—C9A1.376 (2)C20B—C25B1.396 (2)
C8A—C10A1.517 (2)C21B—C22B1.389 (2)
C9A—C26A1.489 (2)C21B—H21B0.9300
C10A—C17A1.512 (2)C22B—C23B1.387 (2)
C10A—C11A1.538 (2)C22B—H22B0.9300
C10A—H10A0.9800C23B—C24B1.386 (2)
C11A—C16A1.392 (2)C23B—H23B0.9300
C11A—C12A1.395 (2)C24B—C25B1.386 (2)
C12A—C13A1.391 (2)C24B—H24B0.9300
C12A—H12A0.9300C25B—H25B0.9300
C13A—C14A1.381 (2)C26B—H26D0.9600
C13A—H13A0.9300C26B—H26E0.9600
C14A—C15A1.381 (3)C26B—H26F0.9600
C14A—H14A0.9300C27B—H27D0.9600
C15A—C16A1.392 (2)C27B—H27E0.9600
C15A—H15A0.9300C27B—H27F0.9600
C16A—H16A0.9300C28—C291.499 (3)
C17A—C19A1.383 (2)C28—H28A0.9600
C17A—C18A1.412 (2)C28—H28B0.9600
C18A—C27A1.491 (2)C28—H28C0.9600
C26A—H26A0.9600C29—O31.414 (2)
C26A—H26B0.9600C29—H29A0.9700
C26A—H26C0.9600C29—H29B0.9700
C27A—H27A0.9600O3—H30.8200
C19A—O2A—H2OA109.5H27A—C27A—H27B109.5
C7A—N1A—N2A109.22 (13)C18A—C27A—H27C109.5
C7A—N1A—C6A128.56 (13)H27A—C27A—H27C109.5
N2A—N1A—C6A121.86 (12)H27B—C27A—H27C109.5
C9A—N2A—N1A107.11 (12)C19B—O2B—H2OB109.5
C9A—N2A—H2NA123.4 (15)C19B—N4B—N3B110.75 (12)
N1A—N2A—H2NA119.1 (15)C19B—N4B—C20B127.71 (13)
C18A—N3A—N4A104.78 (13)N3B—N4B—C20B119.94 (12)
C19A—N4A—N3A110.62 (13)C18B—N3B—N4B104.91 (12)
C19A—N4A—C20A131.0 (4)C9B—N2B—N1B108.23 (13)
N3A—N4A—C20A118.0 (4)C9B—N2B—H2NB123.5 (13)
C19A—N4A—C20C126.9 (4)N1B—N2B—H2NB119.7 (13)
N3A—N4A—C20C122.3 (4)C7B—N1B—N2B108.79 (13)
C20A—N4A—C20C4.7 (7)C7B—N1B—C6B129.47 (14)
C25A—C20A—N4A125.2 (7)N2B—N1B—C6B120.72 (13)
C25A—C20A—C21A115.9 (7)C2B—C1B—C6B118.92 (17)
N4A—C20A—C21A118.0 (7)C2B—C1B—H1BA120.5
C22A—C21A—C20A119.9 (5)C6B—C1B—H1BA120.5
C22A—C21A—H21A120.1C1B—C2B—C3B120.51 (18)
C20A—C21A—H21A120.1C1B—C2B—H2BA119.7
C23A—C22A—C21A121.3 (4)C3B—C2B—H2BA119.7
C23A—C22A—H22A119.4C4B—C3B—C2B120.17 (18)
C21A—C22A—H22A119.4C4B—C3B—H3BA119.9
C24A—C23A—C22A118.5 (5)C2B—C3B—H3BA119.9
C24A—C23A—H23A120.7C3B—C4B—C5B120.34 (17)
C22A—C23A—H23A120.7C3B—C4B—H4BA119.8
C23A—C24A—C25A120.7 (5)C5B—C4B—H4BA119.8
C23A—C24A—H24A119.6C4B—C5B—C6B119.04 (17)
C25A—C24A—H24A119.6C4B—C5B—H5BA120.5
C20A—C25A—C24A122.6 (6)C6B—C5B—H5BA120.5
C20A—C25A—H25A118.7C1B—C6B—C5B121.02 (16)
C24A—C25A—H25A118.7C1B—C6B—N1B119.51 (15)
C21C—C20C—C25C120.5 (7)C5B—C6B—N1B119.47 (15)
C21C—C20C—N4A123.6 (7)O1B—C7B—N1B123.73 (14)
C25C—C20C—N4A115.0 (7)O1B—C7B—C8B129.79 (15)
C20C—C21C—C22C120.2 (6)N1B—C7B—C8B106.47 (13)
C20C—C21C—H21C119.9C9B—C8B—C7B106.70 (14)
C22C—C21C—H21C119.9C9B—C8B—C10B128.39 (14)
C21C—C22C—C23C119.9 (4)C7B—C8B—C10B124.80 (14)
C21C—C22C—H22C120.1N2B—C9B—C8B109.63 (14)
C23C—C22C—H22C120.1N2B—C9B—C26B119.35 (15)
C22C—C23C—C24C118.8 (4)C8B—C9B—C26B131.00 (15)
C22C—C23C—H23C120.6C8B—C10B—C17B112.66 (12)
C24C—C23C—H23C120.6C8B—C10B—C11B112.68 (12)
C25C—C24C—C23C122.1 (5)C17B—C10B—C11B114.10 (13)
C25C—C24C—H24C119.0C8B—C10B—H10B105.5
C23C—C24C—H24C119.0C17B—C10B—H10B105.5
C24C—C25C—C20C116.8 (6)C11B—C10B—H10B105.5
C24C—C25C—H25C121.6C12B—C11B—C16B118.29 (14)
C20C—C25C—H25C121.6C12B—C11B—C10B119.94 (13)
C6A—C1A—C2A119.20 (16)C16B—C11B—C10B121.63 (14)
C6A—C1A—H1AA120.4C13B—C12B—C11B121.02 (15)
C2A—C1A—H1AA120.4C13B—C12B—H12B119.5
C3A—C2A—C1A120.86 (16)C11B—C12B—H12B119.5
C3A—C2A—H2AA119.6C12B—C13B—C14B120.23 (16)
C1A—C2A—H2AA119.6C12B—C13B—H13B119.9
C2A—C3A—C4A119.44 (16)C14B—C13B—H13B119.9
C2A—C3A—H3AA120.3C13B—C14B—C15B119.71 (15)
C4A—C3A—H3AA120.3C13B—C14B—H14B120.1
C3A—C4A—C5A120.51 (17)C15B—C14B—H14B120.1
C3A—C4A—H4AA119.7C14B—C15B—C16B119.92 (15)
C5A—C4A—H4AA119.7C14B—C15B—H15B120.0
C4A—C5A—C6A119.54 (16)C16B—C15B—H15B120.0
C4A—C5A—H5AA120.2C15B—C16B—C11B120.82 (15)
C6A—C5A—H5AA120.2C15B—C16B—H16B119.6
C1A—C6A—C5A120.44 (15)C11B—C16B—H16B119.6
C1A—C6A—N1A119.82 (14)C19B—C17B—C18B104.75 (13)
C5A—C6A—N1A119.71 (14)C19B—C17B—C10B128.64 (13)
O1A—C7A—N1A122.85 (14)C18B—C17B—C10B126.48 (13)
O1A—C7A—C8A130.41 (14)N3B—C18B—C17B112.30 (13)
N1A—C7A—C8A106.74 (13)N3B—C18B—C27B120.25 (13)
C9A—C8A—C7A106.64 (13)C17B—C18B—C27B127.45 (14)
C9A—C8A—C10A128.32 (14)O2B—C19B—N4B119.10 (13)
C7A—C8A—C10A124.87 (13)O2B—C19B—C17B133.62 (14)
N2A—C9A—C8A110.07 (14)N4B—C19B—C17B107.27 (13)
N2A—C9A—C26A119.53 (13)C21B—C20B—C25B120.29 (14)
C8A—C9A—C26A130.39 (14)C21B—C20B—N4B120.75 (14)
C17A—C10A—C8A113.93 (12)C25B—C20B—N4B118.96 (14)
C17A—C10A—C11A113.52 (12)C22B—C21B—C20B119.19 (15)
C8A—C10A—C11A111.00 (13)C22B—C21B—H21B120.4
C17A—C10A—H10A105.9C20B—C21B—H21B120.4
C8A—C10A—H10A105.9C23B—C22B—C21B120.69 (16)
C11A—C10A—H10A105.9C23B—C22B—H22B119.7
C16A—C11A—C12A118.28 (14)C21B—C22B—H22B119.7
C16A—C11A—C10A120.60 (14)C24B—C23B—C22B119.87 (15)
C12A—C11A—C10A121.01 (13)C24B—C23B—H23B120.1
C13A—C12A—C11A121.06 (15)C22B—C23B—H23B120.1
C13A—C12A—H12A119.5C25B—C24B—C23B120.19 (15)
C11A—C12A—H12A119.5C25B—C24B—H24B119.9
C14A—C13A—C12A120.13 (16)C23B—C24B—H24B119.9
C14A—C13A—H13A119.9C24B—C25B—C20B119.77 (15)
C12A—C13A—H13A119.9C24B—C25B—H25B120.1
C15A—C14A—C13A119.30 (15)C20B—C25B—H25B120.1
C15A—C14A—H14A120.4C9B—C26B—H26D109.5
C13A—C14A—H14A120.4C9B—C26B—H26E109.5
C14A—C15A—C16A120.93 (16)H26D—C26B—H26E109.5
C14A—C15A—H15A119.5C9B—C26B—H26F109.5
C16A—C15A—H15A119.5H26D—C26B—H26F109.5
C15A—C16A—C11A120.29 (16)H26E—C26B—H26F109.5
C15A—C16A—H16A119.9C18B—C27B—H27D109.5
C11A—C16A—H16A119.9C18B—C27B—H27E109.5
C19A—C17A—C18A104.20 (14)H27D—C27B—H27E109.5
C19A—C17A—C10A128.55 (15)C18B—C27B—H27F109.5
C18A—C17A—C10A127.25 (14)H27D—C27B—H27F109.5
N3A—C18A—C17A112.25 (14)H27E—C27B—H27F109.5
N3A—C18A—C27A120.42 (15)C29—C28—H28A109.5
C17A—C18A—C27A127.33 (15)C29—C28—H28B109.5
O2A—C19A—N4A119.99 (14)H28A—C28—H28B109.5
O2A—C19A—C17A131.81 (15)C29—C28—H28C109.5
N4A—C19A—C17A108.11 (14)H28A—C28—H28C109.5
C9A—C26A—H26A109.5H28B—C28—H28C109.5
C9A—C26A—H26B109.5O3—C29—C28113.16 (18)
H26A—C26A—H26B109.5O3—C29—H29A108.9
C9A—C26A—H26C109.5C28—C29—H29A108.9
H26A—C26A—H26C109.5O3—C29—H29B108.9
H26B—C26A—H26C109.5C28—C29—H29B108.9
C18A—C27A—H27A109.5H29A—C29—H29B107.8
C18A—C27A—H27B109.5C29—O3—H3109.5
C7A—N1A—N2A—C9A4.81 (17)C20A—N4A—C19A—O2A12.2 (5)
C6A—N1A—N2A—C9A178.43 (14)C20C—N4A—C19A—O2A9.1 (5)
C18A—N3A—N4A—C19A1.23 (16)N3A—N4A—C19A—C17A1.69 (17)
C18A—N3A—N4A—C20A172.3 (4)C20A—N4A—C19A—C17A170.8 (5)
C18A—N3A—N4A—C20C174.5 (4)C20C—N4A—C19A—C17A173.8 (5)
C19A—N4A—C20A—C25A164.5 (5)C18A—C17A—C19A—O2A175.16 (16)
N3A—N4A—C20A—C25A23.5 (9)C10A—C17A—C19A—O2A4.7 (3)
C20C—N4A—C20A—C25A133 (9)C18A—C17A—C19A—N4A1.39 (16)
C19A—N4A—C20A—C21A26.8 (9)C10A—C17A—C19A—N4A178.70 (14)
N3A—N4A—C20A—C21A145.2 (5)C19B—N4B—N3B—C18B0.79 (17)
C20C—N4A—C20A—C21A58 (9)C20B—N4B—N3B—C18B167.49 (14)
C25A—C20A—C21A—C22A10.8 (9)C9B—N2B—N1B—C7B2.77 (17)
N4A—C20A—C21A—C22A179.4 (5)C9B—N2B—N1B—C6B172.31 (13)
C20A—C21A—C22A—C23A3.9 (7)C6B—C1B—C2B—C3B0.9 (3)
C21A—C22A—C23A—C24A3.9 (7)C1B—C2B—C3B—C4B0.1 (3)
C22A—C23A—C24A—C25A4.5 (8)C2B—C3B—C4B—C5B0.4 (3)
N4A—C20A—C25A—C24A179.5 (6)C3B—C4B—C5B—C6B0.2 (3)
C21A—C20A—C25A—C24A10.5 (10)C2B—C1B—C6B—C5B1.2 (3)
C23A—C24A—C25A—C20A3.1 (9)C2B—C1B—C6B—N1B178.64 (16)
C19A—N4A—C20C—C21C11.4 (10)C4B—C5B—C6B—C1B0.6 (3)
N3A—N4A—C20C—C21C163.6 (6)C4B—C5B—C6B—N1B179.18 (16)
C20A—N4A—C20C—C21C139 (9)C7B—N1B—C6B—C1B29.4 (2)
C19A—N4A—C20C—C25C157.5 (4)N2B—N1B—C6B—C1B163.45 (15)
N3A—N4A—C20C—C25C27.5 (8)C7B—N1B—C6B—C5B150.41 (16)
C20A—N4A—C20C—C25C52 (9)N2B—N1B—C6B—C5B16.7 (2)
C25C—C20C—C21C—C22C13.2 (11)N2B—N1B—C7B—O1B178.76 (14)
N4A—C20C—C21C—C22C178.4 (6)C6B—N1B—C7B—O1B10.4 (2)
C20C—C21C—C22C—C23C2.4 (9)N2B—N1B—C7B—C8B0.17 (16)
C21C—C22C—C23C—C24C6.4 (8)C6B—N1B—C7B—C8B168.50 (14)
C22C—C23C—C24C—C25C4.4 (8)O1B—C7B—C8B—C9B178.72 (15)
C23C—C24C—C25C—C20C5.9 (8)N1B—C7B—C8B—C9B2.43 (16)
C21C—C20C—C25C—C24C14.9 (11)O1B—C7B—C8B—C10B4.9 (2)
N4A—C20C—C25C—C24C175.8 (5)N1B—C7B—C8B—C10B173.96 (13)
C6A—C1A—C2A—C3A0.3 (3)N1B—N2B—C9B—C8B4.39 (17)
C1A—C2A—C3A—C4A0.1 (3)N1B—N2B—C9B—C26B174.06 (13)
C2A—C3A—C4A—C5A0.4 (3)C7B—C8B—C9B—N2B4.22 (17)
C3A—C4A—C5A—C6A0.7 (3)C10B—C8B—C9B—N2B171.99 (14)
C2A—C1A—C6A—C5A0.0 (2)C7B—C8B—C9B—C26B173.99 (16)
C2A—C1A—C6A—N1A178.35 (14)C10B—C8B—C9B—C26B9.8 (3)
C4A—C5A—C6A—C1A0.6 (2)C9B—C8B—C10B—C17B109.83 (17)
C4A—C5A—C6A—N1A178.87 (15)C7B—C8B—C10B—C17B74.59 (18)
C7A—N1A—C6A—C1A47.2 (2)C9B—C8B—C10B—C11B119.33 (17)
N2A—N1A—C6A—C1A125.08 (16)C7B—C8B—C10B—C11B56.26 (18)
C7A—N1A—C6A—C5A131.11 (17)C8B—C10B—C11B—C12B168.74 (13)
N2A—N1A—C6A—C5A56.6 (2)C17B—C10B—C11B—C12B38.62 (19)
N2A—N1A—C7A—O1A176.91 (14)C8B—C10B—C11B—C16B15.51 (19)
C6A—N1A—C7A—O1A3.8 (3)C17B—C10B—C11B—C16B145.62 (14)
N2A—N1A—C7A—C8A3.49 (17)C16B—C11B—C12B—C13B0.2 (2)
C6A—N1A—C7A—C8A176.56 (14)C10B—C11B—C12B—C13B175.73 (14)
O1A—C7A—C8A—C9A179.56 (16)C11B—C12B—C13B—C14B0.8 (3)
N1A—C7A—C8A—C9A0.87 (17)C12B—C13B—C14B—C15B0.6 (3)
O1A—C7A—C8A—C10A4.8 (3)C13B—C14B—C15B—C16B0.2 (2)
N1A—C7A—C8A—C10A174.72 (14)C14B—C15B—C16B—C11B0.8 (2)
N1A—N2A—C9A—C8A4.26 (17)C12B—C11B—C16B—C15B0.6 (2)
N1A—N2A—C9A—C26A176.17 (14)C10B—C11B—C16B—C15B176.46 (14)
C7A—C8A—C9A—N2A2.12 (17)C8B—C10B—C17B—C19B59.2 (2)
C10A—C8A—C9A—N2A177.52 (14)C11B—C10B—C17B—C19B70.9 (2)
C7A—C8A—C9A—C26A178.36 (17)C8B—C10B—C17B—C18B115.95 (17)
C10A—C8A—C9A—C26A3.0 (3)C11B—C10B—C17B—C18B113.92 (17)
C9A—C8A—C10A—C17A115.97 (17)N4B—N3B—C18B—C17B0.58 (18)
C7A—C8A—C10A—C17A69.41 (19)N4B—N3B—C18B—C27B179.46 (14)
C9A—C8A—C10A—C11A114.39 (17)C19B—C17B—C18B—N3B0.16 (19)
C7A—C8A—C10A—C11A60.23 (19)C10B—C17B—C18B—N3B175.94 (15)
C17A—C10A—C11A—C16A29.1 (2)C19B—C17B—C18B—C27B179.87 (16)
C8A—C10A—C11A—C16A158.99 (14)C10B—C17B—C18B—C27B4.0 (3)
C17A—C10A—C11A—C12A154.73 (15)N3B—N4B—C19B—O2B179.02 (13)
C8A—C10A—C11A—C12A24.9 (2)C20B—N4B—C19B—O2B13.6 (2)
C16A—C11A—C12A—C13A0.7 (2)N3B—N4B—C19B—C17B0.71 (18)
C10A—C11A—C12A—C13A176.92 (15)C20B—N4B—C19B—C17B166.11 (15)
C11A—C12A—C13A—C14A0.7 (3)C18B—C17B—C19B—O2B179.34 (17)
C12A—C13A—C14A—C15A0.1 (3)C10B—C17B—C19B—O2B3.4 (3)
C13A—C14A—C15A—C16A0.9 (3)C18B—C17B—C19B—N4B0.33 (17)
C14A—C15A—C16A—C11A0.9 (3)C10B—C17B—C19B—N4B176.32 (15)
C12A—C11A—C16A—C15A0.1 (2)C19B—N4B—C20B—C21B48.7 (2)
C10A—C11A—C16A—C15A176.12 (16)N3B—N4B—C20B—C21B147.13 (15)
C8A—C10A—C17A—C19A69.5 (2)C19B—N4B—C20B—C25B130.94 (17)
C11A—C10A—C17A—C19A58.8 (2)N3B—N4B—C20B—C25B33.3 (2)
C8A—C10A—C17A—C18A110.58 (17)C25B—C20B—C21B—C22B0.6 (2)
C11A—C10A—C17A—C18A121.05 (16)N4B—C20B—C21B—C22B178.97 (15)
N4A—N3A—C18A—C17A0.32 (17)C20B—C21B—C22B—C23B0.1 (3)
N4A—N3A—C18A—C27A179.89 (14)C21B—C22B—C23B—C24B0.3 (3)
C19A—C17A—C18A—N3A0.66 (17)C22B—C23B—C24B—C25B0.2 (3)
C10A—C17A—C18A—N3A179.42 (14)C23B—C24B—C25B—C20B0.3 (3)
C19A—C17A—C18A—C27A179.11 (16)C21B—C20B—C25B—C24B0.7 (2)
C10A—C17A—C18A—C27A0.8 (3)N4B—C20B—C25B—C24B178.90 (15)
N3A—N4A—C19A—O2A175.35 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2A—H2OA···O1A0.821.762.5755 (16)173
O3—H3···N3Ai0.822.112.923 (2)173
O2B—H2OB···O1B0.821.682.4970 (16)176
N2A—H2NA···N3Bii0.93 (3)1.88 (3)2.810 (2)176 (2)
N2B—H2NB···O1Aiii0.95 (2)1.75 (2)2.6922 (19)173 (2)
C1B—H1BA···O1B0.932.372.925 (2)118
C2B—H2BA···O3iv0.932.483.313 (2)149
C21A—H21A···O2A0.932.412.910 (5)114
C5B—H5BA···Cg1i0.932.893.595 (3)134
C29—H29B···Cg2iv0.972.803.492 (2)129
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y+1, z; (iii) x+1, y+1, z; (iv) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC27H24N4O2·0.5C2H6O
Mr459.54
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)8.3767 (2), 13.9498 (3), 20.4797 (4)
α, β, γ (°)101.074 (1), 93.723 (1), 93.579 (1)
V3)2336.74 (9)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.38 × 0.26 × 0.17
Data collection
DiffractometerBruker SMART APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.960, 0.986
No. of measured, independent and
observed [I > 2σ(I)] reflections
41677, 13462, 9482
Rint0.043
(sin θ/λ)max1)0.703
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.055, 0.161, 1.03
No. of reflections13462
No. of parameters632
No. of restraints42
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.40, 0.43

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
O2A—H2OA···O1A0.82001.76002.5755 (16)173.00
O3—H3···N3Ai0.82002.11002.923 (2)173.00
O2B—H2OB···O1B0.82001.68002.4970 (16)176.00
N2A—H2NA···N3Bii0.93 (3)1.88 (3)2.810 (2)176 (2)
N2B—H2NB···O1Aiii0.95 (2)1.75 (2)2.6922 (19)173 (2)
C1B—H1BA···O1B0.93002.37002.925 (2)118.00
C2B—H2BA···O3iv0.93002.48003.313 (2)149.00
C21A—H21A···O2A0.93002.41002.910 (5)114.00
C5B—H5BA···Cg1i0.93002.89003.595 (3)134.00
C29—H29B···Cg2iv0.97002.80003.492 (2)129.00
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y+1, z; (iii) x+1, y+1, z; (iv) x+1, y, z.
 

Acknowledgements

HKF and RK thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. RK 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

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Volume 65| Part 1| January 2009| Pages o66-o67
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