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

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ISSN: 2056-9890

(Z)-3-Di­ethyl­amino-6-({2-[(E)-4-(di­ethyl­amino)-2-hy­dr­oxy­benzyl­­idene­amino]-4,5-di­methyl­phen­yl}amino­methyl­­idene)cyclo­hexa-2,4-dienone–5,5′-bis­­(di­ethyl­amino)-2,2′-[4,5-di­methyl-o-phenyl­enebis(nitrilo­methyl­­idyne)]diphenol

aDepartment of Chemistry, School of Science, Payame Noor University (PNU), Ardakan, Yazd, Iran, bDepartment of Chemistry, Science and Research Branch, Islamic Azad University, Tehran, Iran, cX-ray Crystallography Lab., Plasma Physics Research Center, Science and Research Branch, Islamic Azad University, Tehran, Iran, and dDepartment of Physics, University of Sargodha, Punjab, Pakistan
*Correspondence e-mail: rkia@srbiau.ac.ir, zsrkk@yahoo.com, dmntahir_uos@yahoo.com

(Received 25 October 2010; accepted 4 November 2010; online 10 November 2010)

The asymmetric unit of the title Schiff base compound, C30H38N4O2, comprises two crystallographically independent mol­ecules, A and B. The structure is non-merohedrally twinned with a refined BASF ratio of 0.219 (6):0.701 (6). Mol­ecule B shows both phenol–imine and keto–amine tautomeric forms in a single structure. The dihedral angles between the central ring and the two outer rings are 5.9 (3) and 48.4 (3)° in mol­ecule A, and 48.3 (3) and 6.9 (3)° in mol­ecule B. Strong intra­molecular O—H⋯N and N—H⋯O hydrogen bonds generate S(6) ring motifs. The crystal structure is further stabilized by inter­molecular C—H⋯O, C—H⋯π and ππ inter­actions [centroid–centroid distances = 3.870 (4)–3.871 (4) Å].

Related literature

For standard values of bond lengths, 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 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 related structures, see: Kargar et al. (2009[Kargar, H., Kia, R., Jamshidvand, A. & Fun, H.-K. (2009). Acta Cryst. E65, o776-o777.], 2010a[Kargar, H., Kia, R., Ullah Khan, I. & Sahraei, A. (2010a). Acta Cryst. E66, o539.],b[Kargar, H., Kia, R., Khan, I. U., Sahraei, A. & Aberoomand Azar, P. (2010b). Acta Cryst. E66, o728.]).

[Scheme 1]

Experimental

Crystal data
  • C30H38N4O2

  • Mr = 486.64

  • Triclinic, [P \overline 1]

  • a = 11.4430 (12) Å

  • b = 12.0251 (12) Å

  • c = 22.171 (2) Å

  • α = 88.241 (6)°

  • β = 89.370 (7)°

  • γ = 65.207 (6)°

  • V = 2768.2 (5) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.07 mm−1

  • T = 296 K

  • 0.24 × 0.19 × 0.11 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 = 0.983, Tmax = 0.992

  • 44348 measured reflections

  • 9655 independent reflections

  • 4485 reflections with I > 2σ(I)

  • Rint = 0.095

Refinement
  • R[F2 > 2σ(F2)] = 0.106

  • wR(F2) = 0.320

  • S = 1.06

  • 9655 reflections

  • 662 parameters

  • H-atom parameters constrained

  • Δρmax = 0.32 e Å−3

  • Δρmin = −0.40 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1⋯N1 0.91 1.68 2.553 (7) 160
O2—H2⋯N2 0.90 1.79 2.613 (8) 150
O3—H3⋯N5 0.90 1.85 2.627 (8) 143
N6—H6⋯O4 0.85 1.74 2.562 (7) 162
C7—H7A⋯O4 0.93 2.50 3.360 (9) 153
C46—H46A⋯O1i 0.93 2.54 3.373 (9) 149
Symmetry code: (i) x+1, y, z.

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, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

Schiff base ligands are one of the most prevalent systems in coordination chemistry. As part of a general study of tetradenate Schiff bases (Kargar et al., 2009; Kargar et al., 2010a,b), we have determined the crystal structure of the title compound.

The asymmetric unit of the title Schiff base compound, Fig. 1, comprises two crystallographically independent molecules, A and B which is non-merohedrally twinned with a refined BASF ratio of 0.219 (6)/0.701 (6). Molecule B shows both phenol-imine and keto-amine tautomeric form in a single structure. The dihedral angles between the central phenyl ring with the two outer phenyl rings are 5.9 (3) and 48.4 (3)° in molecule A and 48.3 (3) and 6.9 (3)° in molecule B, respectively. Strong intramolecular O—H···N and N—H···O hydrogen bonds generate S(6) ring motifs. The crystal structure is further stabilized by the intermolecular C—H···π and π-π interactions [Cg1···Cg1i = 3.870 (4)Å, (i) -x, 1 - y, 1 - z; Cg2···Cg2ii = 3.871 (4)Å, (ii) 1 - x, 1 - y, -z; Cg1 and Cg2 are the centroids of C15–C20 and C33–C38 benzene rings].

Related literature top

For standard values of bond lengths, see: Allen et al. (1987). For details of hydrogen-bond motifs, see: Bernstein et al. (1995). Kargar et al. (2009, 2010a,b).

Experimental top

The title compound was synthesized by adding 4-N-diethylamino- salicylaldehyde (4 mmol) to a solution of 4,5-dimethyl-1,2-phenylenediamine (2 mmol) in ethanol (20 ml). The mixture was refluxed with stirring for half an hour. The resultant yellow solution was filtered. Yellow single crystals of the title compound suitable for X-ray structure determination were recrystallized from ethanol by slow evaporation of the solvents at room temperature over several days. The quality of the crystal was not optimal and it was weakly diffracting. Although recrystallization was attempted repeatedly, we tried three data collections but no better data than this one was obtained.

Refinement top

H atoms of the hydroxy and amino groups were located in a difference Fourier map. They first restrained to 0.90 (1)Å [OH] and 0.85 (1)Å [NH] and then constrained to refine with the parent atoms with Uiso(H) = 1.5 Ueq(O) and Uiso(H) = 1.2 Ueq(N), see Table 1. The remaining H atoms were positioned geometrically with C-H = 0.93-0.97 Å and included in a riding model approximation with Uiso (H) = 1.2 or 1.5 Ueq (C). A rotating group model was used for the methyl groups.

Structure description top

Schiff base ligands are one of the most prevalent systems in coordination chemistry. As part of a general study of tetradenate Schiff bases (Kargar et al., 2009; Kargar et al., 2010a,b), we have determined the crystal structure of the title compound.

The asymmetric unit of the title Schiff base compound, Fig. 1, comprises two crystallographically independent molecules, A and B which is non-merohedrally twinned with a refined BASF ratio of 0.219 (6)/0.701 (6). Molecule B shows both phenol-imine and keto-amine tautomeric form in a single structure. The dihedral angles between the central phenyl ring with the two outer phenyl rings are 5.9 (3) and 48.4 (3)° in molecule A and 48.3 (3) and 6.9 (3)° in molecule B, respectively. Strong intramolecular O—H···N and N—H···O hydrogen bonds generate S(6) ring motifs. The crystal structure is further stabilized by the intermolecular C—H···π and π-π interactions [Cg1···Cg1i = 3.870 (4)Å, (i) -x, 1 - y, 1 - z; Cg2···Cg2ii = 3.871 (4)Å, (ii) 1 - x, 1 - y, -z; Cg1 and Cg2 are the centroids of C15–C20 and C33–C38 benzene rings].

For standard values of bond lengths, see: Allen et al. (1987). For details of hydrogen-bond motifs, see: Bernstein et al. (1995). Kargar et al. (2009, 2010a,b).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (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, 2009).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of the title compound, showing 30% probability displacement ellipsoids and the atomic numbering. Intramolecular hydrogen bonds are drawn as dashed lines. The H atoms omitted for clarity except those involving in the hydrogen bonds.
[Figure 2] Fig. 2. The crystal packing of the title compound viewed down the c-axis, shows linking of molecules along the a-axis through C—H···O hydrogen bonds. Tha dashed lines show interactions.
(Z)-3-Diethylamino-6-({2-[(E)-4-(diethylamino)-2- hydroxybenzylideneamino]-4,5-dimethylphenyl}aminomethylidene)cyclohexa- 2,4-dienone–5,5'-bis(diethylamino)-2,2'-[4,5-dimethyl-o- phenylenebis(nitrilomethylidyne)]diphenol top
Crystal data top
C30H38N4O2Z = 4
Mr = 486.64F(000) = 1048
Triclinic, P1Dx = 1.168 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 11.4430 (12) ÅCell parameters from 2502 reflections
b = 12.0251 (12) Åθ = 2.5–30.5°
c = 22.171 (2) ŵ = 0.07 mm1
α = 88.241 (6)°T = 296 K
β = 89.370 (7)°Block, yellow
γ = 65.207 (6)°0.24 × 0.19 × 0.11 mm
V = 2768.2 (5) Å3
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
9655 independent reflections
Radiation source: fine-focus sealed tube4485 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.095
φ and ω scansθmax = 25.0°, θmin = 0.9°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
h = 1313
Tmin = 0.983, Tmax = 0.992k = 1414
44348 measured reflectionsl = 126
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)] = 0.106Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.320H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.1053P)2 + 5.0339P]
where P = (Fo2 + 2Fc2)/3
9655 reflections(Δ/σ)max < 0.001
662 parametersΔρmax = 0.32 e Å3
0 restraintsΔρmin = 0.40 e Å3
Crystal data top
C30H38N4O2γ = 65.207 (6)°
Mr = 486.64V = 2768.2 (5) Å3
Triclinic, P1Z = 4
a = 11.4430 (12) ÅMo Kα radiation
b = 12.0251 (12) ŵ = 0.07 mm1
c = 22.171 (2) ÅT = 296 K
α = 88.241 (6)°0.24 × 0.19 × 0.11 mm
β = 89.370 (7)°
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
9655 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
4485 reflections with I > 2σ(I)
Tmin = 0.983, Tmax = 0.992Rint = 0.095
44348 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.1060 restraints
wR(F2) = 0.320H-atom parameters constrained
S = 1.06Δρmax = 0.32 e Å3
9655 reflectionsΔρmin = 0.40 e Å3
662 parameters
Special details top

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

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.1771 (4)0.4531 (4)0.2969 (2)0.0672 (14)
H10.20900.51030.29820.101*
O20.0627 (4)0.6876 (4)0.34677 (19)0.0623 (12)
H20.01120.69730.34280.093*
O30.4368 (4)0.6831 (4)0.15051 (19)0.0657 (13)
H30.51010.69150.15710.099*
O40.6807 (4)0.4524 (4)0.2030 (2)0.0628 (13)
N10.3133 (5)0.5755 (4)0.2929 (2)0.0443 (12)
N20.1449 (5)0.7137 (4)0.3758 (2)0.0473 (13)
N30.2933 (7)0.1058 (6)0.1759 (3)0.090 (2)
N40.3082 (5)0.6070 (5)0.5023 (2)0.0609 (15)
N50.6399 (5)0.7194 (4)0.1182 (2)0.0510 (13)
N60.8132 (5)0.5792 (4)0.2040 (2)0.0480 (13)
H60.75990.54780.19790.058*
N70.1980 (5)0.5983 (5)0.0011 (2)0.0640 (16)
N80.7927 (6)0.1075 (5)0.3372 (3)0.0712 (17)
C10.2550 (6)0.3818 (6)0.2556 (3)0.0525 (17)
C20.2365 (7)0.2816 (6)0.2369 (3)0.0622 (19)
H2A0.16930.26680.25360.075*
C30.3138 (7)0.2029 (6)0.1944 (3)0.0635 (19)
C40.4164 (7)0.2268 (6)0.1695 (3)0.0625 (19)
H4A0.47030.17530.14080.075*
C50.4356 (7)0.3237 (7)0.1875 (3)0.0614 (19)
H5A0.50330.33740.17060.074*
C60.3577 (6)0.4057 (6)0.2310 (3)0.0453 (15)
C70.3832 (6)0.5038 (6)0.2507 (3)0.0476 (16)
H7A0.45050.51760.23350.057*
C80.3370 (6)0.6713 (5)0.3167 (3)0.0427 (15)
C90.4376 (6)0.7001 (6)0.2999 (3)0.0509 (16)
H9A0.49460.65420.27050.061*
C100.4569 (6)0.7951 (6)0.3252 (3)0.0532 (17)
C110.3742 (7)0.8617 (6)0.3700 (3)0.0580 (18)
C120.2731 (7)0.8316 (6)0.3877 (3)0.0544 (17)
H12A0.21830.87570.41820.065*
C130.2515 (6)0.7399 (5)0.3619 (3)0.0458 (15)
C140.1118 (6)0.7099 (6)0.4310 (3)0.0535 (17)
H14A0.16130.72210.46090.064*
C150.0009 (6)0.6875 (5)0.4493 (3)0.0462 (15)
C160.0255 (6)0.6752 (6)0.5095 (3)0.0548 (17)
H16A0.02790.68370.53860.066*
C170.1272 (6)0.6510 (6)0.5281 (3)0.0567 (18)
H17A0.14240.64470.56910.068*
C180.2091 (6)0.6355 (6)0.4851 (3)0.0493 (16)
C190.1828 (6)0.6490 (6)0.4242 (3)0.0534 (17)
H19A0.23540.63970.39490.064*
C200.0815 (6)0.6756 (5)0.4062 (3)0.0466 (15)
C220.1668 (11)0.0945 (8)0.1939 (4)0.104 (3)
H22A0.09740.17470.19950.124*
H22B0.14170.05320.16300.124*
C230.1964 (13)0.0245 (9)0.2488 (5)0.142 (5)
H23A0.11920.02300.26550.212*
H23B0.23250.06070.27690.212*
H23C0.25750.05780.24130.212*
C240.3764 (9)0.0149 (7)0.1341 (4)0.092 (3)
H24A0.37180.06250.14350.110*
H24B0.46450.00310.14070.110*
C250.3448 (12)0.0464 (9)0.0695 (5)0.125 (4)
H25A0.40290.01860.04530.188*
H25B0.35300.12090.05900.188*
H25C0.25800.05750.06210.188*
C260.5640 (8)0.8280 (8)0.3018 (4)0.082 (2)
H26A0.61270.83530.33520.124*
H26B0.52730.90450.27940.124*
H26C0.61960.76500.27600.124*
C270.3887 (9)0.9674 (7)0.3990 (4)0.095 (3)
H27A0.46790.93710.42130.142*
H27B0.31781.00710.42580.142*
H27C0.38951.02500.36820.142*
C290.3988 (6)0.6015 (8)0.4570 (4)0.078 (2)
H29A0.40920.66200.42510.094*
H29B0.48210.62320.47590.094*
C300.3571 (8)0.4787 (9)0.4297 (4)0.098 (3)
H30A0.42430.47900.40400.148*
H30B0.33980.41720.46110.148*
H30C0.28060.46110.40630.148*
C310.3373 (7)0.5918 (6)0.5643 (3)0.065 (2)
H31A0.25730.55680.58700.078*
H31B0.37550.53350.56670.078*
C320.4263 (9)0.7071 (8)0.5938 (4)0.102 (3)
H32A0.44300.68830.63450.153*
H32B0.50580.74310.57170.153*
H32C0.38720.76380.59410.153*
C330.4194 (6)0.6733 (6)0.0906 (3)0.0504 (16)
C340.3201 (6)0.6427 (6)0.0748 (3)0.0551 (17)
H34A0.26910.63040.10490.066*
C350.2952 (6)0.6301 (6)0.0143 (3)0.0521 (17)
C360.3750 (7)0.6504 (6)0.0296 (3)0.0614 (19)
H36A0.36020.64410.07020.074*
C370.4733 (6)0.6790 (6)0.0132 (3)0.0570 (18)
H37A0.52450.69120.04320.068*
C380.4996 (6)0.6905 (5)0.0467 (3)0.0467 (15)
C390.6070 (6)0.7153 (6)0.0633 (3)0.0558 (17)
H39A0.65560.72920.03260.067*
C400.7476 (6)0.7447 (6)0.1312 (3)0.0495 (16)
C410.7670 (7)0.8394 (7)0.1032 (3)0.068 (2)
H41A0.70970.88540.07310.081*
C420.8680 (8)0.8700 (7)0.1176 (4)0.067 (2)
C430.9524 (7)0.8001 (7)0.1628 (4)0.066 (2)
C440.9355 (6)0.7039 (6)0.1913 (3)0.0554 (17)
H44A0.99400.65670.22080.066*
C450.8327 (6)0.6764 (6)0.1768 (3)0.0481 (16)
C460.8779 (6)0.5096 (6)0.2494 (3)0.0466 (15)
H46A0.94230.52570.26710.056*
C470.8537 (5)0.4122 (6)0.2719 (3)0.0437 (15)
C480.9273 (6)0.3351 (6)0.3189 (3)0.0546 (17)
H48A0.99160.35230.33600.065*
C490.9098 (7)0.2369 (6)0.3407 (3)0.0614 (19)
H49A0.96200.18870.37190.074*
C500.8121 (6)0.2061 (6)0.3164 (3)0.0522 (16)
C510.7368 (6)0.2830 (6)0.2700 (3)0.0536 (17)
H51A0.67230.26550.25330.064*
C520.7536 (6)0.3841 (6)0.2475 (3)0.0466 (15)
C540.1720 (7)0.5812 (6)0.0635 (3)0.066 (2)
H54A0.13550.52160.06430.079*
H54B0.25250.54840.08550.079*
C550.0812 (9)0.6977 (8)0.0946 (4)0.101 (3)
H55A0.05840.67960.13340.151*
H55B0.12230.75260.09960.151*
H55C0.00500.73560.07070.151*
C560.1057 (7)0.5896 (8)0.0441 (4)0.076 (2)
H56A0.02390.60930.02420.091*
H56B0.09160.65040.07440.091*
C570.1492 (8)0.4652 (9)0.0751 (4)0.094 (3)
H57A0.08620.46680.10440.140*
H57B0.23020.44460.09480.140*
H57C0.15890.40490.04570.140*
C580.8813 (11)0.9777 (8)0.0858 (5)0.120 (4)
H58A0.88591.03260.11530.180*
H58B0.80801.02020.06010.180*
H58C0.95830.94840.06200.180*
C591.0633 (8)0.8279 (8)0.1837 (4)0.091 (3)
H59A1.10800.84070.14920.137*
H59B1.12160.76010.20790.137*
H59C1.03020.90030.20720.137*
C610.8788 (9)0.0184 (7)0.3812 (4)0.085 (3)
H61A0.96420.01630.37720.102*
H61B0.88490.06240.37260.102*
C620.8333 (11)0.0484 (9)0.4446 (4)0.123 (4)
H62A0.89550.00870.47200.184*
H62B0.75240.04320.44980.184*
H62C0.82280.13000.45270.184*
C630.6915 (8)0.0789 (7)0.3124 (3)0.076 (2)
H63A0.61650.15440.30320.092*
H63B0.66660.03210.34210.092*
C640.7357 (11)0.0071 (8)0.2564 (4)0.110 (3)
H64A0.66690.00900.24040.165*
H64B0.80790.06910.26580.165*
H64C0.76090.05320.22700.165*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.055 (3)0.077 (3)0.085 (4)0.041 (3)0.024 (3)0.035 (3)
O20.059 (3)0.087 (3)0.051 (3)0.041 (3)0.000 (2)0.004 (2)
O30.061 (3)0.091 (4)0.056 (3)0.042 (3)0.002 (2)0.009 (3)
O40.051 (3)0.076 (3)0.069 (3)0.035 (3)0.020 (2)0.018 (3)
N10.045 (3)0.049 (3)0.045 (3)0.025 (3)0.002 (2)0.009 (3)
N20.047 (3)0.048 (3)0.052 (3)0.025 (3)0.005 (3)0.011 (3)
N30.100 (6)0.078 (5)0.116 (6)0.058 (4)0.027 (4)0.043 (4)
N40.043 (3)0.083 (4)0.061 (4)0.031 (3)0.001 (3)0.008 (3)
N50.044 (3)0.046 (3)0.067 (4)0.022 (3)0.000 (3)0.003 (3)
N60.048 (3)0.045 (3)0.059 (4)0.028 (3)0.001 (3)0.007 (3)
N70.049 (3)0.084 (4)0.060 (4)0.028 (3)0.004 (3)0.015 (3)
N80.080 (4)0.049 (4)0.094 (5)0.037 (3)0.000 (4)0.007 (3)
C10.047 (4)0.053 (4)0.060 (4)0.023 (3)0.005 (3)0.018 (3)
C20.066 (5)0.058 (5)0.075 (5)0.039 (4)0.018 (4)0.018 (4)
C30.066 (5)0.055 (4)0.078 (5)0.033 (4)0.001 (4)0.016 (4)
C40.054 (4)0.065 (5)0.066 (5)0.021 (4)0.012 (4)0.025 (4)
C50.052 (4)0.077 (5)0.062 (5)0.033 (4)0.013 (4)0.019 (4)
C60.036 (3)0.052 (4)0.049 (4)0.020 (3)0.001 (3)0.006 (3)
C70.047 (4)0.058 (4)0.047 (4)0.030 (3)0.003 (3)0.002 (3)
C80.041 (4)0.043 (4)0.052 (4)0.025 (3)0.004 (3)0.002 (3)
C90.050 (4)0.047 (4)0.065 (4)0.030 (3)0.002 (3)0.004 (3)
C100.049 (4)0.058 (4)0.063 (4)0.034 (3)0.003 (3)0.004 (4)
C110.070 (5)0.049 (4)0.069 (5)0.038 (4)0.011 (4)0.001 (4)
C120.066 (5)0.046 (4)0.060 (4)0.032 (4)0.008 (3)0.007 (3)
C130.047 (4)0.043 (4)0.054 (4)0.025 (3)0.007 (3)0.001 (3)
C140.041 (4)0.047 (4)0.069 (5)0.015 (3)0.010 (3)0.000 (3)
C150.041 (4)0.042 (4)0.053 (4)0.015 (3)0.000 (3)0.007 (3)
C160.054 (4)0.061 (4)0.053 (4)0.028 (4)0.005 (3)0.004 (3)
C170.057 (4)0.067 (5)0.050 (4)0.029 (4)0.006 (3)0.005 (3)
C180.042 (4)0.048 (4)0.054 (4)0.016 (3)0.003 (3)0.003 (3)
C190.042 (4)0.060 (4)0.062 (5)0.025 (3)0.005 (3)0.001 (3)
C200.043 (4)0.050 (4)0.045 (4)0.017 (3)0.003 (3)0.006 (3)
C220.173 (11)0.065 (6)0.081 (6)0.057 (6)0.044 (7)0.002 (5)
C230.198 (13)0.096 (8)0.131 (10)0.062 (8)0.073 (9)0.011 (7)
C240.117 (8)0.057 (5)0.106 (7)0.040 (5)0.003 (6)0.027 (5)
C250.164 (11)0.097 (8)0.109 (9)0.047 (7)0.002 (8)0.022 (6)
C260.073 (5)0.088 (6)0.113 (7)0.060 (5)0.005 (5)0.012 (5)
C270.111 (7)0.080 (6)0.122 (7)0.069 (6)0.006 (6)0.024 (5)
C290.033 (4)0.120 (7)0.081 (6)0.033 (4)0.005 (4)0.023 (5)
C300.075 (6)0.134 (9)0.110 (7)0.066 (6)0.003 (5)0.018 (6)
C310.056 (4)0.063 (5)0.070 (5)0.018 (4)0.018 (4)0.002 (4)
C320.084 (6)0.089 (7)0.111 (7)0.015 (5)0.027 (5)0.011 (5)
C330.045 (4)0.054 (4)0.049 (4)0.016 (3)0.004 (3)0.008 (3)
C340.045 (4)0.063 (4)0.057 (4)0.022 (3)0.007 (3)0.009 (3)
C350.043 (4)0.053 (4)0.057 (4)0.017 (3)0.006 (3)0.005 (3)
C360.059 (5)0.070 (5)0.052 (4)0.024 (4)0.008 (4)0.003 (4)
C370.051 (4)0.065 (5)0.053 (4)0.022 (4)0.001 (3)0.006 (3)
C380.042 (4)0.038 (4)0.057 (4)0.014 (3)0.003 (3)0.002 (3)
C390.058 (4)0.048 (4)0.058 (5)0.020 (3)0.002 (4)0.004 (3)
C400.052 (4)0.043 (4)0.059 (4)0.026 (3)0.008 (3)0.013 (3)
C410.071 (5)0.061 (5)0.078 (5)0.034 (4)0.008 (4)0.002 (4)
C420.082 (6)0.060 (5)0.080 (5)0.050 (4)0.011 (4)0.008 (4)
C430.066 (5)0.052 (4)0.097 (6)0.041 (4)0.015 (4)0.021 (4)
C440.055 (4)0.057 (4)0.062 (4)0.030 (4)0.007 (3)0.015 (3)
C450.042 (4)0.043 (4)0.067 (4)0.026 (3)0.007 (3)0.009 (3)
C460.044 (4)0.054 (4)0.050 (4)0.028 (3)0.002 (3)0.009 (3)
C470.030 (3)0.051 (4)0.052 (4)0.020 (3)0.001 (3)0.007 (3)
C480.051 (4)0.066 (5)0.055 (4)0.031 (4)0.008 (3)0.007 (4)
C490.054 (4)0.060 (5)0.072 (5)0.027 (4)0.009 (4)0.004 (4)
C500.052 (4)0.051 (4)0.057 (4)0.025 (3)0.007 (3)0.006 (3)
C510.047 (4)0.048 (4)0.068 (5)0.022 (3)0.010 (3)0.002 (3)
C520.038 (4)0.051 (4)0.050 (4)0.018 (3)0.001 (3)0.002 (3)
C540.057 (4)0.070 (5)0.063 (5)0.017 (4)0.019 (4)0.007 (4)
C550.095 (7)0.083 (6)0.101 (7)0.014 (5)0.031 (5)0.012 (5)
C560.040 (4)0.105 (7)0.086 (6)0.031 (4)0.003 (4)0.028 (5)
C570.072 (6)0.120 (8)0.096 (7)0.048 (6)0.005 (5)0.005 (6)
C580.144 (10)0.081 (7)0.164 (10)0.076 (7)0.006 (8)0.011 (6)
C590.082 (6)0.087 (6)0.134 (8)0.064 (5)0.011 (5)0.024 (5)
C610.102 (7)0.052 (5)0.100 (7)0.030 (5)0.008 (5)0.009 (5)
C620.163 (11)0.105 (8)0.085 (7)0.043 (7)0.029 (7)0.021 (6)
C630.111 (7)0.074 (5)0.072 (5)0.066 (5)0.024 (5)0.009 (4)
C640.153 (10)0.084 (6)0.108 (8)0.062 (7)0.038 (7)0.030 (6)
Geometric parameters (Å, º) top
O1—C11.326 (7)C27—H27B0.9600
O1—H10.9059C27—H27C0.9600
O2—C201.346 (7)C29—C301.495 (11)
O2—H20.9029C29—H29A0.9700
O3—C331.361 (7)C29—H29B0.9700
O3—H30.8998C30—H30A0.9600
O4—C521.319 (7)C30—H30B0.9600
N1—C71.309 (7)C30—H30C0.9600
N1—C81.407 (7)C31—C321.498 (10)
N2—C141.283 (8)C31—H31A0.9700
N2—C131.411 (7)C31—H31B0.9700
N3—C31.359 (8)C32—H32A0.9600
N3—C241.459 (10)C32—H32B0.9600
N3—C221.556 (12)C32—H32C0.9600
N4—C181.363 (8)C33—C341.384 (9)
N4—C311.435 (8)C33—C381.401 (9)
N4—C291.475 (9)C34—C351.401 (9)
N5—C391.287 (8)C34—H34A0.9300
N5—C401.423 (8)C35—C361.411 (9)
N6—C461.307 (7)C36—C371.363 (9)
N6—C451.397 (7)C36—H36A0.9300
N6—H60.8542C37—C381.388 (8)
N7—C351.368 (8)C37—H37A0.9300
N7—C541.455 (8)C38—C391.434 (9)
N7—C561.481 (9)C39—H39A0.9300
N8—C501.362 (8)C40—C411.378 (9)
N8—C631.458 (9)C40—C451.394 (9)
N8—C611.463 (10)C41—C421.394 (10)
C1—C21.384 (8)C41—H41A0.9300
C1—C61.422 (8)C42—C431.390 (10)
C2—C31.379 (9)C42—C581.517 (10)
C2—H2A0.9300C43—C441.384 (9)
C3—C41.422 (9)C43—C591.521 (10)
C4—C51.346 (9)C44—C451.393 (8)
C4—H4A0.9300C44—H44A0.9300
C5—C61.413 (8)C46—C471.390 (8)
C5—H5A0.9300C46—H46A0.9300
C6—C71.410 (8)C47—C481.400 (8)
C7—H7A0.9300C47—C521.438 (8)
C8—C91.379 (8)C48—C491.353 (9)
C8—C131.413 (8)C48—H48A0.9300
C9—C101.385 (8)C49—C501.432 (9)
C9—H9A0.9300C49—H49A0.9300
C10—C111.385 (9)C50—C511.397 (9)
C10—C261.519 (9)C51—C521.386 (8)
C11—C121.398 (9)C51—H51A0.9300
C11—C271.511 (9)C54—C551.501 (10)
C12—C131.369 (8)C54—H54A0.9700
C12—H12A0.9300C54—H54B0.9700
C14—C151.455 (9)C55—H55A0.9600
C14—H14A0.9300C55—H55B0.9600
C15—C161.382 (8)C55—H55C0.9600
C15—C201.402 (8)C56—C571.509 (11)
C16—C171.369 (9)C56—H56A0.9700
C16—H16A0.9300C56—H56B0.9700
C17—C181.412 (9)C57—H57A0.9600
C17—H17A0.9300C57—H57B0.9600
C18—C191.400 (9)C57—H57C0.9600
C19—C201.378 (8)C58—H58A0.9600
C19—H19A0.9300C58—H58B0.9600
C22—C231.420 (12)C58—H58C0.9600
C22—H22A0.9700C59—H59A0.9600
C22—H22B0.9700C59—H59B0.9600
C23—H23A0.9600C59—H59C0.9600
C23—H23B0.9600C61—C621.495 (12)
C23—H23C0.9600C61—H61A0.9700
C24—C251.480 (12)C61—H61B0.9700
C24—H24A0.9700C62—H62A0.9600
C24—H24B0.9700C62—H62B0.9600
C25—H25A0.9600C62—H62C0.9600
C25—H25B0.9600C63—C641.492 (10)
C25—H25C0.9600C63—H63A0.9700
C26—H26A0.9600C63—H63B0.9700
C26—H26B0.9600C64—H64A0.9600
C26—H26C0.9600C64—H64B0.9600
C27—H27A0.9600C64—H64C0.9600
C1—O1—H199.1C32—C31—H31A108.5
C20—O2—H2107.2N4—C31—H31B108.5
C33—O3—H3111.0C32—C31—H31B108.5
C7—N1—C8123.9 (5)H31A—C31—H31B107.5
C14—N2—C13119.7 (5)C31—C32—H32A109.5
C3—N3—C24124.4 (7)C31—C32—H32B109.5
C3—N3—C22119.8 (7)H32A—C32—H32B109.5
C24—N3—C22115.5 (6)C31—C32—H32C109.5
C18—N4—C31122.9 (6)H32A—C32—H32C109.5
C18—N4—C29120.4 (6)H32B—C32—H32C109.5
C31—N4—C29116.5 (6)O3—C33—C34117.0 (6)
C39—N5—C40120.7 (6)O3—C33—C38121.9 (6)
C46—N6—C45126.5 (5)C34—C33—C38121.0 (6)
C46—N6—H699.8C33—C34—C35121.1 (6)
C45—N6—H6133.7C33—C34—H34A119.4
C35—N7—C54122.2 (6)C35—C34—H34A119.4
C35—N7—C56121.9 (6)N7—C35—C34121.0 (6)
C54—N7—C56115.7 (6)N7—C35—C36121.8 (6)
C50—N8—C63121.2 (6)C34—C35—C36117.2 (6)
C50—N8—C61122.3 (6)C37—C36—C35121.0 (6)
C63—N8—C61116.2 (6)C37—C36—H36A119.5
O1—C1—C2119.1 (6)C35—C36—H36A119.5
O1—C1—C6121.1 (5)C36—C37—C38122.3 (6)
C2—C1—C6119.8 (6)C36—C37—H37A118.9
C3—C2—C1122.5 (6)C38—C37—H37A118.9
C3—C2—H2A118.7C37—C38—C33117.4 (6)
C1—C2—H2A118.7C37—C38—C39121.6 (6)
N3—C3—C2121.8 (7)C33—C38—C39121.0 (6)
N3—C3—C4120.4 (7)N5—C39—C38123.9 (6)
C2—C3—C4117.9 (6)N5—C39—H39A118.1
C5—C4—C3120.2 (6)C38—C39—H39A118.1
C5—C4—H4A119.9C41—C40—C45118.3 (6)
C3—C4—H4A119.9C41—C40—N5122.6 (6)
C4—C5—C6123.0 (6)C45—C40—N5119.0 (6)
C4—C5—H5A118.5C40—C41—C42123.5 (7)
C6—C5—H5A118.5C40—C41—H41A118.2
C7—C6—C5121.8 (6)C42—C41—H41A118.2
C7—C6—C1121.5 (6)C43—C42—C41117.2 (7)
C5—C6—C1116.6 (6)C43—C42—C58122.2 (7)
N1—C7—C6120.9 (6)C41—C42—C58120.5 (8)
N1—C7—H7A119.5C44—C43—C42120.3 (6)
C6—C7—H7A119.5C44—C43—C59117.8 (8)
C9—C8—N1124.8 (6)C42—C43—C59121.8 (7)
C9—C8—C13118.8 (5)C43—C44—C45121.3 (7)
N1—C8—C13116.3 (5)C43—C44—H44A119.4
C8—C9—C10122.4 (6)C45—C44—H44A119.4
C8—C9—H9A118.8C44—C45—C40119.2 (6)
C10—C9—H9A118.8C44—C45—N6123.0 (6)
C9—C10—C11119.0 (6)C40—C45—N6117.7 (5)
C9—C10—C26119.9 (6)N6—C46—C47122.0 (5)
C11—C10—C26121.0 (6)N6—C46—H46A119.0
C10—C11—C12118.7 (6)C47—C46—H46A119.0
C10—C11—C27121.7 (7)C46—C47—C48121.5 (5)
C12—C11—C27119.5 (7)C46—C47—C52121.8 (6)
C13—C12—C11122.6 (6)C48—C47—C52116.7 (6)
C13—C12—H12A118.7C49—C48—C47123.3 (6)
C11—C12—H12A118.7C49—C48—H48A118.3
C12—C13—N2123.7 (6)C47—C48—H48A118.3
C12—C13—C8118.4 (6)C48—C49—C50120.9 (6)
N2—C13—C8117.8 (5)C48—C49—H49A119.5
N2—C14—C15123.4 (6)C50—C49—H49A119.5
N2—C14—H14A118.3N8—C50—C51121.3 (6)
C15—C14—H14A118.3N8—C50—C49122.2 (6)
C16—C15—C20117.9 (6)C51—C50—C49116.5 (6)
C16—C15—C14121.3 (6)C52—C51—C50123.0 (6)
C20—C15—C14120.8 (6)C52—C51—H51A118.5
C17—C16—C15122.6 (6)C50—C51—H51A118.5
C17—C16—H16A118.7O4—C52—C51120.3 (6)
C15—C16—H16A118.7O4—C52—C47120.1 (6)
C16—C17—C18120.2 (6)C51—C52—C47119.6 (6)
C16—C17—H17A119.9N7—C54—C55113.0 (6)
C18—C17—H17A119.9N7—C54—H54A109.0
N4—C18—C19121.5 (6)C55—C54—H54A109.0
N4—C18—C17121.4 (6)N7—C54—H54B109.0
C19—C18—C17117.1 (6)C55—C54—H54B109.0
C20—C19—C18122.1 (6)H54A—C54—H54B107.8
C20—C19—H19A119.0C54—C55—H55A109.5
C18—C19—H19A119.0C54—C55—H55B109.5
O2—C20—C19118.6 (5)H55A—C55—H55B109.5
O2—C20—C15121.3 (6)C54—C55—H55C109.5
C19—C20—C15120.1 (6)H55A—C55—H55C109.5
C23—C22—N3104.9 (9)H55B—C55—H55C109.5
C23—C22—H22A110.8N7—C56—C57114.0 (6)
N3—C22—H22A110.8N7—C56—H56A108.8
C23—C22—H22B110.8C57—C56—H56A108.8
N3—C22—H22B110.8N7—C56—H56B108.8
H22A—C22—H22B108.8C57—C56—H56B108.8
C22—C23—H23A109.5H56A—C56—H56B107.7
C22—C23—H23B109.5C56—C57—H57A109.5
H23A—C23—H23B109.5C56—C57—H57B109.5
C22—C23—H23C109.5H57A—C57—H57B109.5
H23A—C23—H23C109.5C56—C57—H57C109.5
H23B—C23—H23C109.5H57A—C57—H57C109.5
N3—C24—C25115.0 (8)H57B—C57—H57C109.5
N3—C24—H24A108.5C42—C58—H58A109.5
C25—C24—H24A108.5C42—C58—H58B109.5
N3—C24—H24B108.5H58A—C58—H58B109.5
C25—C24—H24B108.5C42—C58—H58C109.5
H24A—C24—H24B107.5H58A—C58—H58C109.5
C24—C25—H25A109.5H58B—C58—H58C109.5
C24—C25—H25B109.5C43—C59—H59A109.5
H25A—C25—H25B109.5C43—C59—H59B109.5
C24—C25—H25C109.5H59A—C59—H59B109.5
H25A—C25—H25C109.5C43—C59—H59C109.5
H25B—C25—H25C109.5H59A—C59—H59C109.5
C10—C26—H26A109.5H59B—C59—H59C109.5
C10—C26—H26B109.5N8—C61—C62112.3 (7)
H26A—C26—H26B109.5N8—C61—H61A109.1
C10—C26—H26C109.5C62—C61—H61A109.1
H26A—C26—H26C109.5N8—C61—H61B109.1
H26B—C26—H26C109.5C62—C61—H61B109.1
C11—C27—H27A109.5H61A—C61—H61B107.9
C11—C27—H27B109.5C61—C62—H62A109.5
H27A—C27—H27B109.5C61—C62—H62B109.5
C11—C27—H27C109.5H62A—C62—H62B109.5
H27A—C27—H27C109.5C61—C62—H62C109.5
H27B—C27—H27C109.5H62A—C62—H62C109.5
N4—C29—C30113.8 (6)H62B—C62—H62C109.5
N4—C29—H29A108.8N8—C63—C64111.0 (7)
C30—C29—H29A108.8N8—C63—H63A109.4
N4—C29—H29B108.8C64—C63—H63A109.4
C30—C29—H29B108.8N8—C63—H63B109.4
H29A—C29—H29B107.7C64—C63—H63B109.4
C29—C30—H30A109.5H63A—C63—H63B108.0
C29—C30—H30B109.5C63—C64—H64A109.5
H30A—C30—H30B109.5C63—C64—H64B109.5
C29—C30—H30C109.5H64A—C64—H64B109.5
H30A—C30—H30C109.5C63—C64—H64C109.5
H30B—C30—H30C109.5H64A—C64—H64C109.5
N4—C31—C32114.9 (6)H64B—C64—H64C109.5
N4—C31—H31A108.5
O1—C1—C2—C3179.7 (7)O3—C33—C34—C35179.8 (6)
C6—C1—C2—C30.5 (11)C38—C33—C34—C351.1 (10)
C24—N3—C3—C2175.9 (8)C54—N7—C35—C34178.3 (6)
C22—N3—C3—C211.0 (12)C56—N7—C35—C347.1 (10)
C24—N3—C3—C44.8 (13)C54—N7—C35—C361.1 (10)
C22—N3—C3—C4168.4 (7)C56—N7—C35—C36173.5 (7)
C1—C2—C3—N3179.1 (7)C33—C34—C35—N7179.1 (6)
C1—C2—C3—C40.3 (11)C33—C34—C35—C360.3 (9)
N3—C3—C4—C5179.3 (7)N7—C35—C36—C37178.4 (6)
C2—C3—C4—C50.1 (11)C34—C35—C36—C371.1 (10)
C3—C4—C5—C60.0 (11)C35—C36—C37—C380.5 (10)
C4—C5—C6—C7177.5 (6)C36—C37—C38—C330.9 (10)
C4—C5—C6—C10.3 (10)C36—C37—C38—C39177.2 (6)
O1—C1—C6—C71.9 (10)O3—C33—C38—C37179.7 (6)
C2—C1—C6—C7177.3 (6)C34—C33—C38—C371.7 (9)
O1—C1—C6—C5179.6 (6)O3—C33—C38—C392.2 (9)
C2—C1—C6—C50.5 (9)C34—C33—C38—C39176.4 (6)
C8—N1—C7—C6176.9 (5)C40—N5—C39—C38179.9 (6)
C5—C6—C7—N1177.0 (6)C37—C38—C39—N5175.6 (6)
C1—C6—C7—N10.6 (9)C33—C38—C39—N52.4 (10)
C7—N1—C8—C91.5 (9)C39—N5—C40—C4147.0 (9)
C7—N1—C8—C13179.8 (6)C39—N5—C40—C45137.3 (6)
N1—C8—C9—C10179.5 (6)C45—C40—C41—C420.6 (10)
C13—C8—C9—C100.9 (9)N5—C40—C41—C42176.4 (6)
C8—C9—C10—C111.7 (10)C40—C41—C42—C430.0 (11)
C8—C9—C10—C26175.8 (6)C40—C41—C42—C58178.5 (7)
C9—C10—C11—C120.8 (10)C41—C42—C43—C440.4 (11)
C26—C10—C11—C12176.7 (6)C58—C42—C43—C44178.9 (7)
C9—C10—C11—C27179.2 (7)C41—C42—C43—C59177.9 (7)
C26—C10—C11—C271.8 (11)C58—C42—C43—C590.6 (12)
C10—C11—C12—C130.9 (10)C42—C43—C44—C451.5 (10)
C27—C11—C12—C13177.6 (7)C59—C43—C44—C45176.9 (6)
C11—C12—C13—N2175.2 (6)C43—C44—C45—C402.1 (9)
C11—C12—C13—C81.7 (10)C43—C44—C45—N6179.2 (6)
C14—N2—C13—C1244.7 (9)C41—C40—C45—C441.6 (9)
C14—N2—C13—C8138.4 (6)N5—C40—C45—C44177.6 (5)
C9—C8—C13—C120.8 (9)C41—C40—C45—N6178.8 (6)
N1—C8—C13—C12178.0 (5)N5—C40—C45—N65.2 (8)
C9—C8—C13—N2176.3 (5)C46—N6—C45—C447.0 (9)
N1—C8—C13—N24.9 (8)C46—N6—C45—C40175.9 (6)
C13—N2—C14—C15177.9 (5)C45—N6—C46—C47177.8 (6)
N2—C14—C15—C16175.1 (6)N6—C46—C47—C48177.3 (6)
N2—C14—C15—C203.7 (9)N6—C46—C47—C521.5 (9)
C20—C15—C16—C170.6 (10)C46—C47—C48—C49177.6 (6)
C14—C15—C16—C17178.3 (6)C52—C47—C48—C491.3 (10)
C15—C16—C17—C181.0 (10)C47—C48—C49—C500.3 (11)
C31—N4—C18—C19179.6 (6)C63—N8—C50—C510.8 (10)
C29—N4—C18—C196.1 (10)C61—N8—C50—C51173.3 (7)
C31—N4—C18—C170.6 (10)C63—N8—C50—C49179.1 (6)
C29—N4—C18—C17174.9 (6)C61—N8—C50—C496.7 (10)
C16—C17—C18—N4177.6 (6)C48—C49—C50—N8179.6 (6)
C16—C17—C18—C191.5 (9)C48—C49—C50—C510.4 (10)
N4—C18—C19—C20178.8 (6)N8—C50—C51—C52179.9 (6)
C17—C18—C19—C200.3 (9)C49—C50—C51—C520.1 (10)
C18—C19—C20—O2179.7 (6)C50—C51—C52—O4179.0 (6)
C18—C19—C20—C151.4 (10)C50—C51—C52—C470.9 (10)
C16—C15—C20—O2179.3 (6)C46—C47—C52—O40.8 (9)
C14—C15—C20—O21.8 (9)C48—C47—C52—O4179.7 (6)
C16—C15—C20—C191.8 (9)C46—C47—C52—C51177.4 (6)
C14—C15—C20—C19177.1 (6)C48—C47—C52—C511.5 (9)
C3—N3—C22—C2391.3 (9)C35—N7—C54—C5588.1 (9)
C24—N3—C22—C2394.9 (9)C56—N7—C54—C5586.8 (9)
C3—N3—C24—C2587.8 (11)C35—N7—C56—C5788.4 (8)
C22—N3—C24—C2585.7 (10)C54—N7—C56—C5796.7 (7)
C18—N4—C29—C3088.3 (8)C50—N8—C61—C6293.5 (9)
C31—N4—C29—C3097.1 (8)C63—N8—C61—C6292.1 (9)
C18—N4—C31—C3288.0 (9)C50—N8—C63—C6483.9 (9)
C29—N4—C31—C3286.5 (9)C61—N8—C63—C6490.6 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.911.682.553 (7)160
O2—H2···N20.901.792.613 (8)150
O3—H3···N50.901.852.627 (8)143
N6—H6···O40.851.742.562 (7)162
C7—H7A···O40.932.503.360 (9)153
C46—H46A···O1i0.932.543.373 (9)149
Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC30H38N4O2
Mr486.64
Crystal system, space groupTriclinic, P1
Temperature (K)296
a, b, c (Å)11.4430 (12), 12.0251 (12), 22.171 (2)
α, β, γ (°)88.241 (6), 89.370 (7), 65.207 (6)
V3)2768.2 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.07
Crystal size (mm)0.24 × 0.19 × 0.11
Data collection
DiffractometerBruker SMART APEXII CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.983, 0.992
No. of measured, independent and
observed [I > 2σ(I)] reflections
44348, 9655, 4485
Rint0.095
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.106, 0.320, 1.06
No. of reflections9655
No. of parameters662
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.32, 0.40

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.911.682.553 (7)160
O2—H2···N20.901.792.613 (8)150
O3—H3···N50.901.852.627 (8)143
N6—H6···O40.851.742.562 (7)162
C7—H7A···O40.932.503.360 (9)153
C46—H46A···O1i0.932.543.373 (9)149
Symmetry code: (i) x+1, y, z.
 

Footnotes

Thomson Reuters Researcher ID: A-5471-2009.

Acknowledgements

HK thanks PNU for financial support. RK thanks the Science and Research Branch of the Islamic Azad University, Tehran. MNT thanks the University of Sargodha, Pakistan for the Research facility.

References

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First citationKargar, H., Kia, R., Ullah Khan, I. & Sahraei, A. (2010a). Acta Cryst. E66, o539.  Web of Science CSD CrossRef IUCr Journals Google Scholar
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