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Acta Crystallogr Sect E Struct Rep Online. 2010 February 1; 66(Pt 2): o273.
Published online 2010 January 9. doi:  10.1107/S1600536809054865
PMCID: PMC2979726

Ethyl 2-{[(1Z)-(3-methyl-5-oxo-1-phenyl-4,5-dihydro-1H-pyrazol-4-yl­idene)(p-tol­yl)meth­yl]amino}-3-phenyl­propanoate

Abstract

The asymmetric unit of the title compound, C29H29N3O3, contains two mol­ecules, which exist in their enamine–keto form, being stabilized by strong intra­molecular N—H(...)O hydrogen bonds, which generate S(6) loops. In the crystal, inter­molecular C–H(...)O hydrogen bonds link the mol­ecules into chains, which are further linked by weak C—H(...)π inter­actions, forming a two-dimensional network.

Related literature

For general background to Schiff base compounds in coordination chemistry, see: Habibi et al. (2007 [triangle]). For the anti­bacterial properties of Schiff bases derived from 4-acyl-5-pyrazolones and their metal complexes, see: Li et al. (1997 [triangle], 2004 [triangle]). For the anti­bacterial and biological activity of amino acid esters, see: Xiong et al. (1993 [triangle]). For related structures, see: Wang et al. (2003 [triangle]); Zhang et al. (2004 [triangle]). For further synthetic details, see: Remya et al. (2005 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0o273-scheme1.jpg

Experimental

Crystal data

  • C29H29N3O3
  • M r = 467.55
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o273-efi1.jpg
  • a = 11.0637 (11) Å
  • b = 13.2746 (14) Å
  • c = 20.299 (2) Å
  • α = 101.869 (2)°
  • β = 97.923 (2)°
  • γ = 112.861 (2)°
  • V = 2608.8 (5) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 296 K
  • 0.38 × 0.32 × 0.26 mm

Data collection

  • Bruker SMART CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 1999 [triangle]) T min = 0.971, T max = 0.980
  • 13503 measured reflections
  • 9153 independent reflections
  • 5450 reflections with I > 2σ(I)
  • R int = 0.021

Refinement

  • R[F 2 > 2σ(F 2)] = 0.048
  • wR(F 2) = 0.132
  • S = 1.01
  • 9153 reflections
  • 636 parameters
  • H-atom parameters constrained
  • Δρmax = 0.18 e Å−3
  • Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 1999 [triangle]); cell refinement: SAINT (Bruker, 1999 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809054865/hb5268sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809054865/hb5268Isup2.hkl

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

Acknowledgments

This work was supported by the National Natural Science Foundation of China (No. 20771083).

supplementary crystallographic information

Comment

In recent years, Schiff base compounds play an important role in the development of coordination chemistry related to catalysis and enzymatic reactions, magnetism, and molecular architectures (Habibi et al., 2007). The structures of Schiff bases derived from 4-acyl-5-pyrazolones and their metal complexes have been studied widely for their high antibacterial activation (Li et al., 1997, 2004). Both 1-phenyl-3-methyl-4-toluoyl-5-pyrazolone, Hpmtp, and its metal complexes are widely used and well known for their analgesic activity (Remya et al., 2005). Since amino acid esters also possess good antibacterial and biological activations (Xiong et al., 1993), we have studied the reactions of Hpmtp and amino acid esters.

In the molecule of the title compound, (I), (Fig.1) there are two molecules in the asymmetric unit, and the numerical results given here are for one of them; they are not significantly different. Atoms O1, C7, C8, C11 and N3 form a plane, the largest deviation being 0.0310 Å for atom C11. The dihedral angle between this mean plane and the pyrazolone ring is 1.52 (4)°, indicating that they are essentially coplanar, as seen in 4-{[3,4-dihydro-5-methyl-3-oxo-2-phenyl-2H-pyrazol-4-ylidene]-(phenyl) methyl] amino}-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one(3.56 (3)°;Wang et al.,2003). The bond lengths within this part of the molecule lie between classical single- and double-bond lengths, indicating extensive conjugation. Atoms N3, C19, C27 and O2 are not coplanar, the torsion angle being 22.5 (3)°, different from that in some other 4-acyl-5-prazolone Schiff bases (Zhang et al., 2004; Wang et al., 2003). The bond lengths in this part of the molecule indicate that only C27=O2 is a classical double bond and the other bonds are classical single bonds. The dihedral angle between the benzene ring of ethyl 2-amino-3-phenyl-propanoate and the pyrazolone ring is 63.95 (2)°, reducing steric hindrance. A strong intramolecular N–H···O hydrogen bond is observed (Table 1), stabilizing the enamine-keto form.

In the crystal structure, inter-molecular C–H···O hydrogen bonds (Table 1) link the molecules into 1-D chain (Fig.2), which is further linked by weak C–H···π interactions (Table 1) to form a two-dimensional network (Fig.3), in which they may be effective in the stabilization of the structure.

Experimental

The title compound was synthesized by refluxing a mixture of 1-phenyl-3-methyl-4-toluoyl-5-pyrazolone (15 mmol) (Remya et al., 2005) and phenylalanine ethyl ester (15 mmol) in ethanol (100 ml) for about 5 h. The product was recrystallized from ethanol, affording pale yellow crystals suitable for X-ray analysis.

Refinement

All H atoms were positioned geometrically (N–H = 0.86Å and C–H = 0.93–0.97Å) and treated as riding, with Uiso(H)= 1.2Ueq(C); the Uiso value for the H atoms bonded to N atoms was refined freely. The ethyl group was found to be disordered and was refined as two components with equal occupancy, with the acid of restraints on geometry and displacement parameters.

Figures

Fig. 1.
A view of (I), showing displacement ellipsoids drawn at the 30% probability level. The intra-molecular hydrogen bond is indicated by dashed line.
Fig. 2.
The one-dimensional plane of (I) formed by the intermolecular C–H···O weak hydrogen-bonding interactions.
Fig. 3.
The two-dimensional supra-molecular network of (I) produced by the inter-molecular C–H ···π interactions.

Crystal data

C29H29N3O3Z = 4
Mr = 467.55F(000) = 992
Triclinic, P1Dx = 1.190 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 11.0637 (11) ÅCell parameters from 2516 reflections
b = 13.2746 (14) Åθ = 2.3–20.2°
c = 20.299 (2) ŵ = 0.08 mm1
α = 101.869 (2)°T = 296 K
β = 97.923 (2)°Block, yellow
γ = 112.861 (2)°0.38 × 0.32 × 0.26 mm
V = 2608.8 (5) Å3

Data collection

Bruker SMART CCD diffractometer9153 independent reflections
Radiation source: fine-focus sealed tube5450 reflections with I > 2σ(I)
graphiteRint = 0.021
ω scansθmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 1999)h = −13→11
Tmin = 0.971, Tmax = 0.980k = −10→15
13503 measured reflectionsl = −24→23

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132H-atom parameters constrained
S = 1.01w = 1/[σ2(Fo2) + (0.0568P)2 + 0.1678P] where P = (Fo2 + 2Fc2)/3
9153 reflections(Δ/σ)max = 0.001
636 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = −0.19 e Å3

Special details

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)

xyzUiso*/Ueq
O10.71923 (17)0.81845 (14)0.49334 (9)0.0766 (5)
O20.3638 (2)0.8629 (2)0.49767 (10)0.1062 (7)
O30.29842 (17)0.92431 (15)0.59120 (9)0.0799 (5)
O40.24307 (14)0.80519 (12)1.00473 (7)0.0631 (4)
O5−0.08684 (17)0.87650 (15)1.01365 (8)0.0776 (5)
O6−0.25145 (15)0.84962 (13)0.92501 (7)0.0649 (4)
N10.77524 (18)0.66606 (16)0.49565 (9)0.0609 (5)
N20.74399 (19)0.57817 (16)0.52761 (9)0.0616 (5)
N30.55387 (18)0.82573 (16)0.57946 (9)0.0617 (5)
H3A0.58570.84290.54490.074*
N40.29698 (16)0.65042 (14)0.99683 (9)0.0513 (4)
N50.23374 (18)0.53247 (14)0.96488 (9)0.0547 (5)
N6−0.01134 (18)0.73294 (15)0.92980 (9)0.0598 (5)
H60.04990.77850.96660.072*
C10.9533 (3)0.6259 (2)0.45793 (15)0.0834 (8)
H10.95430.58680.49100.100*
C21.0407 (3)0.6352 (3)0.4136 (2)0.1111 (11)
H21.10010.60160.41710.133*
C31.0397 (4)0.6932 (3)0.3653 (2)0.1202 (13)
H31.09880.69930.33640.144*
C40.9522 (3)0.7420 (3)0.35953 (17)0.1045 (10)
H40.95150.78090.32630.125*
C50.8643 (3)0.7342 (2)0.40263 (14)0.0801 (8)
H50.80500.76790.39870.096*
C60.8655 (2)0.6759 (2)0.45169 (13)0.0667 (7)
C70.7118 (2)0.7346 (2)0.51423 (11)0.0591 (6)
C80.6389 (2)0.68835 (18)0.56273 (10)0.0520 (5)
C90.6635 (2)0.59172 (19)0.56667 (11)0.0551 (6)
C100.6086 (3)0.5064 (2)0.60524 (12)0.0732 (7)
H10A0.63910.44790.59400.110*
H10B0.51160.47290.59230.110*
H10C0.63970.54350.65420.110*
C110.5662 (2)0.73839 (18)0.59647 (10)0.0508 (5)
C120.5048 (2)0.69619 (18)0.65205 (10)0.0497 (5)
C130.3756 (2)0.6121 (2)0.63623 (11)0.0634 (6)
H130.32230.58570.59120.076*
C140.3246 (3)0.5665 (2)0.68735 (12)0.0720 (7)
H140.23680.50950.67600.086*
C150.3998 (3)0.6030 (2)0.75424 (12)0.0689 (7)
C160.5282 (3)0.6890 (2)0.76938 (12)0.0757 (7)
H160.58100.71590.81450.091*
C170.5807 (2)0.7364 (2)0.71958 (11)0.0648 (6)
H170.66720.79540.73150.078*
C180.3415 (3)0.5521 (3)0.80965 (15)0.1137 (11)
H18A0.27490.57760.82100.170*
H18B0.41260.57600.85040.170*
H18C0.30030.47040.79250.170*
C190.4935 (2)0.89585 (19)0.61186 (11)0.0596 (6)
H190.45960.86850.65000.071*
C200.5985 (2)1.0210 (2)0.64057 (12)0.0695 (7)
H20A0.64001.04460.60390.083*
H20B0.55251.06810.65430.083*
C210.7078 (2)1.04170 (19)0.70174 (12)0.0595 (6)
C220.8205 (2)1.0246 (2)0.69331 (13)0.0709 (7)
H220.83040.99990.64890.085*
C230.9190 (3)1.0439 (2)0.75043 (16)0.0812 (8)
H230.99461.03200.74430.097*
C240.9055 (3)1.0806 (2)0.81618 (15)0.0781 (8)
H240.97231.09430.85450.094*
C250.7943 (3)1.0970 (2)0.82516 (14)0.0806 (8)
H250.78461.12150.86960.097*
C260.6963 (3)1.0772 (2)0.76821 (13)0.0758 (7)
H260.62021.08800.77480.091*
C270.3774 (3)0.8892 (2)0.55943 (14)0.0695 (7)
C280.1891 (3)0.9351 (3)0.54875 (16)0.0943 (9)
H28A0.13420.86440.51250.113*
H28B0.22570.99550.52710.113*
C290.1067 (3)0.9618 (3)0.59471 (19)0.1302 (13)
H29A0.06460.89860.61260.195*
H29B0.03840.97590.56900.195*
H29C0.16361.02840.63250.195*
C300.4752 (2)0.7986 (2)1.09284 (12)0.0640 (6)
H300.42030.83581.10020.077*
C310.6034 (3)0.8419 (2)1.13540 (14)0.0793 (7)
H310.63490.90871.17140.095*
C320.6846 (3)0.7867 (3)1.12470 (16)0.0868 (8)
H320.77000.81531.15410.104*
C330.6400 (3)0.6900 (3)1.07104 (16)0.0837 (8)
H330.69580.65371.06330.100*
C340.5129 (2)0.6461 (2)1.02831 (13)0.0667 (6)
H340.48280.58010.99180.080*
C350.4297 (2)0.70014 (18)1.03960 (11)0.0527 (5)
C360.2138 (2)0.70135 (18)0.98212 (10)0.0486 (5)
C370.0921 (2)0.61086 (17)0.93655 (10)0.0472 (5)
C380.1131 (2)0.50964 (17)0.92975 (10)0.0503 (5)
C390.0195 (2)0.38911 (18)0.89275 (12)0.0700 (7)
H39A0.01120.37700.84370.105*
H39B−0.06760.37250.90240.105*
H39C0.05440.33990.90820.105*
C40−0.0169 (2)0.62915 (18)0.90837 (10)0.0486 (5)
C41−0.1392 (2)0.54022 (17)0.85620 (10)0.0490 (5)
C42−0.1335 (2)0.4956 (2)0.78968 (11)0.0642 (6)
H42−0.05100.51930.77750.077*
C43−0.2494 (3)0.4158 (2)0.74106 (12)0.0730 (7)
H43−0.24360.38650.69650.088*
C44−0.3731 (3)0.3787 (2)0.75699 (13)0.0706 (7)
C45−0.3777 (2)0.4225 (2)0.82360 (14)0.0722 (7)
H45−0.46010.39750.83580.087*
C46−0.2635 (2)0.5025 (2)0.87262 (12)0.0620 (6)
H46−0.26980.53140.91710.074*
C47−0.5008 (3)0.2919 (2)0.70330 (15)0.1088 (11)
H47A−0.47780.26590.66120.163*
H47B−0.56070.32650.69420.163*
H47C−0.54480.22830.72060.163*
C48−0.0969 (2)0.77755 (18)0.89797 (11)0.0546 (6)
H48−0.17600.71460.86440.065*
C49−0.0201 (2)0.86357 (19)0.86083 (12)0.0654 (6)
H49A−0.08070.89140.84010.078*
H49B0.05390.92820.89500.078*
C500.0360 (2)0.81547 (19)0.80509 (12)0.0611 (6)
C510.1668 (3)0.8278 (2)0.81830 (15)0.0867 (8)
H510.22260.86630.86260.104*
C520.2163 (3)0.7838 (3)0.76661 (19)0.1075 (10)
H520.30500.79240.77640.129*
C530.1357 (4)0.7275 (3)0.70104 (17)0.1027 (10)
H530.16990.69930.66600.123*
C540.0062 (3)0.7131 (3)0.68762 (14)0.0938 (9)
H54−0.04960.67360.64340.113*
C55−0.0432 (3)0.7568 (2)0.73906 (13)0.0792 (7)
H55−0.13260.74640.72900.095*
C56−0.1432 (2)0.83904 (18)0.95348 (12)0.0559 (6)
C57−0.3000 (2)0.9187 (2)0.96945 (12)0.0712 (7)
H57A−0.23620.99840.98270.085*
H57B−0.31040.89491.01120.085*
C58−0.4329 (3)0.9022 (2)0.92927 (14)0.0898 (8)
H58A−0.42280.92020.88630.135*
H58B−0.46430.95160.95580.135*
H58C−0.49730.82440.91990.135*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0967 (13)0.0666 (11)0.0890 (12)0.0408 (10)0.0529 (10)0.0364 (10)
O20.1053 (15)0.157 (2)0.0633 (12)0.0714 (15)0.0118 (11)0.0198 (13)
O30.0790 (12)0.0933 (13)0.0854 (12)0.0542 (11)0.0211 (10)0.0268 (10)
O40.0664 (10)0.0462 (9)0.0731 (10)0.0302 (8)0.0019 (8)0.0076 (8)
O50.0844 (12)0.0958 (13)0.0531 (10)0.0533 (11)0.0010 (9)0.0034 (9)
O60.0677 (10)0.0708 (11)0.0603 (9)0.0456 (9)0.0032 (8)0.0033 (8)
N10.0631 (12)0.0593 (12)0.0646 (12)0.0269 (10)0.0288 (10)0.0165 (10)
N20.0683 (12)0.0587 (12)0.0589 (11)0.0290 (10)0.0182 (10)0.0138 (10)
N30.0771 (13)0.0679 (13)0.0563 (11)0.0393 (11)0.0305 (10)0.0248 (10)
N40.0500 (11)0.0447 (11)0.0613 (11)0.0261 (9)0.0077 (9)0.0117 (9)
N50.0607 (12)0.0452 (11)0.0615 (11)0.0280 (9)0.0113 (10)0.0136 (9)
N60.0675 (12)0.0537 (12)0.0559 (11)0.0363 (10)−0.0058 (9)0.0042 (9)
C10.0691 (17)0.0748 (18)0.099 (2)0.0304 (15)0.0289 (16)0.0060 (15)
C20.083 (2)0.091 (2)0.155 (3)0.0365 (19)0.059 (2)0.008 (2)
C30.110 (3)0.091 (3)0.157 (3)0.028 (2)0.092 (3)0.021 (2)
C40.120 (3)0.084 (2)0.118 (2)0.035 (2)0.078 (2)0.0294 (19)
C50.0825 (19)0.0724 (18)0.0863 (18)0.0255 (15)0.0465 (16)0.0224 (15)
C60.0580 (15)0.0572 (15)0.0730 (16)0.0168 (12)0.0272 (13)0.0028 (13)
C70.0584 (14)0.0550 (15)0.0615 (14)0.0218 (12)0.0206 (12)0.0124 (12)
C80.0537 (13)0.0542 (13)0.0488 (12)0.0230 (11)0.0177 (10)0.0131 (11)
C90.0577 (14)0.0597 (15)0.0465 (12)0.0260 (12)0.0109 (11)0.0118 (11)
C100.0963 (19)0.0688 (17)0.0644 (15)0.0409 (15)0.0259 (14)0.0242 (13)
C110.0477 (12)0.0528 (14)0.0436 (12)0.0165 (11)0.0078 (10)0.0088 (10)
C120.0508 (13)0.0546 (13)0.0423 (12)0.0233 (11)0.0123 (10)0.0088 (10)
C130.0614 (15)0.0665 (16)0.0465 (13)0.0158 (13)0.0101 (11)0.0093 (12)
C140.0735 (16)0.0625 (16)0.0628 (16)0.0111 (13)0.0263 (14)0.0123 (13)
C150.0896 (19)0.0717 (17)0.0528 (15)0.0370 (16)0.0308 (14)0.0194 (13)
C160.0830 (19)0.104 (2)0.0425 (13)0.0455 (18)0.0106 (13)0.0170 (14)
C170.0558 (14)0.0799 (17)0.0482 (14)0.0245 (13)0.0083 (11)0.0087 (13)
C180.155 (3)0.123 (3)0.088 (2)0.060 (2)0.066 (2)0.056 (2)
C190.0682 (15)0.0646 (15)0.0545 (13)0.0357 (13)0.0191 (12)0.0175 (12)
C200.0818 (17)0.0656 (16)0.0653 (15)0.0384 (14)0.0125 (13)0.0174 (13)
C210.0676 (15)0.0531 (14)0.0584 (15)0.0268 (12)0.0148 (12)0.0157 (11)
C220.0697 (17)0.0745 (17)0.0682 (16)0.0282 (14)0.0213 (14)0.0224 (13)
C230.0619 (17)0.0771 (19)0.103 (2)0.0280 (15)0.0158 (16)0.0279 (17)
C240.082 (2)0.0573 (16)0.0770 (19)0.0183 (14)−0.0039 (15)0.0207 (14)
C250.094 (2)0.0754 (19)0.0606 (16)0.0312 (17)0.0121 (16)0.0096 (14)
C260.0777 (17)0.0802 (19)0.0651 (17)0.0374 (15)0.0150 (14)0.0062 (14)
C270.0703 (17)0.0749 (18)0.0681 (18)0.0339 (15)0.0199 (14)0.0227 (14)
C280.0720 (18)0.093 (2)0.121 (2)0.0429 (17)0.0049 (18)0.0337 (19)
C290.110 (3)0.145 (3)0.185 (4)0.088 (3)0.056 (3)0.069 (3)
C300.0568 (15)0.0622 (16)0.0718 (16)0.0288 (13)0.0098 (13)0.0141 (13)
C310.0630 (17)0.0732 (18)0.0826 (18)0.0192 (15)0.0029 (14)0.0134 (14)
C320.0466 (15)0.092 (2)0.109 (2)0.0200 (16)0.0009 (15)0.0339 (19)
C330.0530 (16)0.086 (2)0.118 (2)0.0347 (15)0.0158 (16)0.0331 (19)
C340.0590 (15)0.0660 (16)0.0834 (17)0.0333 (13)0.0197 (13)0.0236 (13)
C350.0488 (13)0.0527 (14)0.0617 (14)0.0247 (11)0.0125 (11)0.0216 (12)
C360.0538 (13)0.0473 (13)0.0527 (13)0.0282 (11)0.0133 (10)0.0172 (11)
C370.0514 (13)0.0460 (12)0.0505 (12)0.0281 (11)0.0103 (10)0.0139 (10)
C380.0570 (14)0.0468 (13)0.0497 (12)0.0252 (11)0.0112 (11)0.0146 (10)
C390.0757 (16)0.0449 (14)0.0826 (17)0.0272 (13)0.0033 (13)0.0124 (12)
C400.0576 (13)0.0498 (13)0.0448 (12)0.0278 (11)0.0139 (10)0.0160 (10)
C410.0560 (13)0.0470 (13)0.0480 (13)0.0279 (11)0.0078 (11)0.0135 (10)
C420.0650 (15)0.0743 (17)0.0573 (15)0.0386 (14)0.0113 (12)0.0117 (13)
C430.0835 (19)0.0774 (18)0.0542 (15)0.0437 (16)0.0008 (14)0.0027 (13)
C440.0768 (18)0.0536 (15)0.0696 (17)0.0253 (14)−0.0079 (14)0.0158 (13)
C450.0599 (15)0.0656 (17)0.0803 (18)0.0141 (13)0.0089 (14)0.0302 (15)
C460.0644 (16)0.0639 (15)0.0572 (14)0.0239 (13)0.0173 (12)0.0221 (12)
C470.096 (2)0.082 (2)0.106 (2)0.0169 (18)−0.0275 (18)0.0158 (18)
C480.0609 (14)0.0509 (13)0.0538 (13)0.0333 (12)0.0023 (11)0.0075 (11)
C490.0808 (17)0.0587 (15)0.0656 (15)0.0418 (14)0.0127 (13)0.0156 (12)
C500.0661 (16)0.0585 (15)0.0641 (15)0.0339 (13)0.0132 (13)0.0162 (12)
C510.0710 (18)0.100 (2)0.0845 (19)0.0420 (17)0.0091 (15)0.0132 (16)
C520.076 (2)0.141 (3)0.117 (3)0.062 (2)0.029 (2)0.025 (2)
C530.107 (3)0.136 (3)0.089 (2)0.072 (2)0.042 (2)0.028 (2)
C540.101 (2)0.116 (3)0.0665 (18)0.058 (2)0.0163 (17)0.0102 (16)
C550.0745 (17)0.099 (2)0.0676 (17)0.0487 (16)0.0117 (15)0.0125 (15)
C560.0560 (14)0.0507 (13)0.0566 (15)0.0250 (11)0.0038 (12)0.0082 (11)
C570.0790 (17)0.0708 (17)0.0755 (16)0.0488 (15)0.0207 (14)0.0098 (13)
C580.0792 (19)0.098 (2)0.105 (2)0.0576 (17)0.0228 (16)0.0164 (17)

Geometric parameters (Å, °)

O1—C71.248 (3)C24—C251.358 (4)
O2—C271.201 (3)C24—H240.9300
O3—C271.320 (3)C25—C261.374 (3)
O3—C281.457 (3)C25—H250.9300
O4—C361.252 (2)C26—H260.9300
O5—C561.195 (2)C28—C291.475 (4)
O6—C561.327 (2)C28—H28A0.9700
O6—C571.456 (2)C28—H28B0.9700
N1—C71.375 (3)C29—H29A0.9600
N1—N21.401 (2)C29—H29B0.9600
N1—C61.415 (3)C29—H29C0.9600
N2—C91.309 (3)C30—C351.374 (3)
N3—C111.325 (3)C30—C311.383 (3)
N3—C191.449 (3)C30—H300.9300
N3—H3A0.8600C31—C321.376 (4)
N4—C361.373 (2)C31—H310.9300
N4—N51.403 (2)C32—C331.364 (4)
N4—C351.416 (3)C32—H320.9300
N5—C381.310 (2)C33—C341.374 (3)
N6—C401.331 (2)C33—H330.9300
N6—C481.445 (2)C34—C351.385 (3)
N6—H60.8600C34—H340.9300
C1—C61.378 (3)C36—C371.433 (3)
C1—C21.396 (4)C37—C401.390 (3)
C1—H10.9300C37—C381.433 (3)
C2—C31.366 (5)C38—C391.483 (3)
C2—H20.9300C39—H39A0.9600
C3—C41.364 (4)C39—H39B0.9600
C3—H30.9300C39—H39C0.9600
C4—C51.383 (3)C40—C411.482 (3)
C4—H40.9300C41—C421.379 (3)
C5—C61.383 (3)C41—C461.383 (3)
C5—H50.9300C42—C431.381 (3)
C7—C81.443 (3)C42—H420.9300
C8—C111.392 (3)C43—C441.373 (3)
C8—C91.426 (3)C43—H430.9300
C9—C101.492 (3)C44—C451.374 (3)
C10—H10A0.9600C44—C471.518 (3)
C10—H10B0.9600C45—C461.375 (3)
C10—H10C0.9600C45—H450.9300
C11—C121.491 (3)C46—H460.9300
C12—C131.371 (3)C47—H47A0.9600
C12—C171.379 (3)C47—H47B0.9600
C13—C141.384 (3)C47—H47C0.9600
C13—H130.9300C48—C561.518 (3)
C14—C151.370 (3)C48—C491.540 (3)
C14—H140.9300C48—H480.9800
C15—C161.375 (3)C49—C501.510 (3)
C15—C181.521 (3)C49—H49A0.9700
C16—C171.377 (3)C49—H49B0.9700
C16—H160.9300C50—C511.372 (3)
C17—H170.9300C50—C551.374 (3)
C18—H18A0.9599C51—C521.378 (4)
C18—H18B0.9600C51—H510.9300
C18—H18C0.9600C52—C531.368 (4)
C19—C271.512 (3)C52—H520.9300
C19—C201.538 (3)C53—C541.350 (4)
C19—H190.9800C53—H530.9300
C20—C211.506 (3)C54—C551.371 (3)
C20—H20A0.9700C54—H540.9300
C20—H20B0.9700C55—H550.9300
C21—C261.375 (3)C57—C581.491 (3)
C21—C221.378 (3)C57—H57A0.9700
C22—C231.382 (3)C57—H57B0.9700
C22—H220.9300C58—H58A0.9600
C23—C241.373 (3)C58—H58B0.9600
C23—H230.9300C58—H58C0.9600
C27—O3—C28118.0 (2)C29—C28—H28B110.2
C56—O6—C57117.64 (17)H28A—C28—H28B108.5
C7—N1—N2111.98 (17)C28—C29—H29A109.5
C7—N1—C6128.7 (2)C28—C29—H29B109.5
N2—N1—C6119.28 (19)H29A—C29—H29B109.5
C9—N2—N1106.36 (17)C28—C29—H29C109.5
C11—N3—C19128.05 (18)H29A—C29—H29C109.5
C11—N3—H3A116.0H29B—C29—H29C109.5
C19—N3—H3A116.0C35—C30—C31119.5 (2)
C36—N4—N5111.77 (16)C35—C30—H30120.2
C36—N4—C35129.02 (18)C31—C30—H30120.2
N5—N4—C35119.18 (16)C32—C31—C30120.3 (3)
C38—N5—N4106.38 (16)C32—C31—H31119.9
C40—N6—C48127.15 (18)C30—C31—H31119.9
C40—N6—H6116.4C33—C32—C31120.0 (3)
C48—N6—H6116.4C33—C32—H32120.0
C6—C1—C2118.7 (3)C31—C32—H32120.0
C6—C1—H1120.7C32—C33—C34120.3 (3)
C2—C1—H1120.7C32—C33—H33119.9
C3—C2—C1120.7 (3)C34—C33—H33119.9
C3—C2—H2119.7C33—C34—C35120.0 (2)
C1—C2—H2119.7C33—C34—H34120.0
C4—C3—C2120.1 (3)C35—C34—H34120.0
C4—C3—H3119.9C30—C35—C34119.9 (2)
C2—C3—H3119.9C30—C35—N4121.19 (19)
C3—C4—C5120.5 (3)C34—C35—N4118.9 (2)
C3—C4—H4119.7O4—C36—N4125.45 (19)
C5—C4—H4119.7O4—C36—C37129.52 (18)
C6—C5—C4119.4 (3)N4—C36—C37105.02 (17)
C6—C5—H5120.3C40—C37—C38132.1 (2)
C4—C5—H5120.3C40—C37—C36122.48 (18)
C1—C6—C5120.6 (2)C38—C37—C36105.47 (17)
C1—C6—N1119.3 (2)N5—C38—C37111.32 (19)
C5—C6—N1120.1 (2)N5—C38—C39118.58 (19)
O1—C7—N1126.4 (2)C37—C38—C39130.0 (2)
O1—C7—C8129.1 (2)C38—C39—H39A109.5
N1—C7—C8104.5 (2)C38—C39—H39B109.5
C11—C8—C9132.3 (2)H39A—C39—H39B109.5
C11—C8—C7122.2 (2)C38—C39—H39C109.5
C9—C8—C7105.55 (18)H39A—C39—H39C109.5
N2—C9—C8111.57 (19)H39B—C39—H39C109.5
N2—C9—C10118.3 (2)N6—C40—C37118.00 (19)
C8—C9—C10130.1 (2)N6—C40—C41117.83 (18)
C9—C10—H10A109.5C37—C40—C41124.17 (18)
C9—C10—H10B109.5C42—C41—C46118.2 (2)
H10A—C10—H10B109.5C42—C41—C40121.3 (2)
C9—C10—H10C109.5C46—C41—C40120.46 (19)
H10A—C10—H10C109.5C41—C42—C43120.4 (2)
H10B—C10—H10C109.5C41—C42—H42119.8
N3—C11—C8119.18 (19)C43—C42—H42119.8
N3—C11—C12120.08 (18)C44—C43—C42121.5 (2)
C8—C11—C12120.7 (2)C44—C43—H43119.2
C13—C12—C17119.0 (2)C42—C43—H43119.2
C13—C12—C11120.66 (18)C43—C44—C45117.6 (2)
C17—C12—C11120.16 (19)C43—C44—C47121.5 (3)
C12—C13—C14119.9 (2)C45—C44—C47120.9 (3)
C12—C13—H13120.0C44—C45—C46121.7 (2)
C14—C13—H13120.0C44—C45—H45119.2
C15—C14—C13121.8 (2)C46—C45—H45119.2
C15—C14—H14119.1C45—C46—C41120.5 (2)
C13—C14—H14119.1C45—C46—H46119.8
C14—C15—C16117.4 (2)C41—C46—H46119.8
C14—C15—C18121.0 (3)C44—C47—H47A109.5
C16—C15—C18121.7 (2)C44—C47—H47B109.5
C15—C16—C17121.9 (2)H47A—C47—H47B109.5
C15—C16—H16119.1C44—C47—H47C109.5
C17—C16—H16119.1H47A—C47—H47C109.5
C16—C17—C12119.9 (2)H47B—C47—H47C109.5
C16—C17—H17120.0N6—C48—C56109.45 (17)
C12—C17—H17120.0N6—C48—C49111.18 (18)
C15—C18—H18A109.5C56—C48—C49107.89 (17)
C15—C18—H18B109.5N6—C48—H48109.4
H18A—C18—H18B109.5C56—C48—H48109.4
C15—C18—H18C109.5C49—C48—H48109.4
H18A—C18—H18C109.5C50—C49—C48114.14 (18)
H18B—C18—H18C109.5C50—C49—H49A108.7
N3—C19—C27110.08 (19)C48—C49—H49A108.7
N3—C19—C20110.38 (19)C50—C49—H49B108.7
C27—C19—C20108.61 (18)C48—C49—H49B108.7
N3—C19—H19109.2H49A—C49—H49B107.6
C27—C19—H19109.2C51—C50—C55117.6 (2)
C20—C19—H19109.2C51—C50—C49121.6 (2)
C21—C20—C19113.60 (19)C55—C50—C49120.8 (2)
C21—C20—H20A108.8C50—C51—C52120.7 (3)
C19—C20—H20A108.8C50—C51—H51119.6
C21—C20—H20B108.8C52—C51—H51119.6
C19—C20—H20B108.8C53—C52—C51120.3 (3)
H20A—C20—H20B107.7C53—C52—H52119.8
C26—C21—C22118.0 (2)C51—C52—H52119.8
C26—C21—C20120.3 (2)C54—C53—C52119.5 (3)
C22—C21—C20121.7 (2)C54—C53—H53120.2
C21—C22—C23120.4 (2)C52—C53—H53120.2
C21—C22—H22119.8C53—C54—C55120.2 (3)
C23—C22—H22119.8C53—C54—H54119.9
C24—C23—C22120.2 (3)C55—C54—H54119.9
C24—C23—H23119.9C54—C55—C50121.6 (2)
C22—C23—H23119.9C54—C55—H55119.2
C25—C24—C23119.9 (3)C50—C55—H55119.2
C25—C24—H24120.0O5—C56—O6125.0 (2)
C23—C24—H24120.0O5—C56—C48124.8 (2)
C24—C25—C26119.7 (3)O6—C56—C48110.16 (18)
C24—C25—H25120.2O6—C57—C58107.41 (19)
C26—C25—H25120.2O6—C57—H57A110.2
C25—C26—C21121.8 (2)C58—C57—H57A110.2
C25—C26—H26119.1O6—C57—H57B110.2
C21—C26—H26119.1C58—C57—H57B110.2
O2—C27—O3124.7 (2)H57A—C57—H57B108.5
O2—C27—C19124.7 (2)C57—C58—H58A109.5
O3—C27—C19110.4 (2)C57—C58—H58B109.5
O3—C28—C29107.6 (2)H58A—C58—H58B109.5
O3—C28—H28A110.2C57—C58—H58C109.5
C29—C28—H28A110.2H58A—C58—H58C109.5
O3—C28—H28B110.2H58B—C58—H58C109.5
C7—N1—N2—C9−0.9 (2)C20—C19—C27—O3−77.0 (2)
C6—N1—N2—C9177.74 (19)C27—O3—C28—C29173.4 (2)
C36—N4—N5—C380.9 (2)C35—C30—C31—C32−0.2 (4)
C35—N4—N5—C38179.14 (17)C30—C31—C32—C331.4 (4)
C6—C1—C2—C30.3 (5)C31—C32—C33—C34−1.3 (4)
C1—C2—C3—C4−0.5 (5)C32—C33—C34—C350.1 (4)
C2—C3—C4—C50.5 (5)C31—C30—C35—C34−1.0 (3)
C3—C4—C5—C6−0.3 (5)C31—C30—C35—N4177.2 (2)
C2—C1—C6—C5−0.1 (4)C33—C34—C35—C301.0 (3)
C2—C1—C6—N1179.3 (2)C33—C34—C35—N4−177.2 (2)
C4—C5—C6—C10.1 (4)C36—N4—C35—C3025.2 (3)
C4—C5—C6—N1−179.3 (2)N5—N4—C35—C30−152.77 (19)
C7—N1—C6—C1157.5 (2)C36—N4—C35—C34−156.7 (2)
N2—N1—C6—C1−20.9 (3)N5—N4—C35—C3425.4 (3)
C7—N1—C6—C5−23.1 (4)N5—N4—C36—O4178.62 (19)
N2—N1—C6—C5158.5 (2)C35—N4—C36—O40.6 (3)
N2—N1—C7—O1−179.0 (2)N5—N4—C36—C37−1.7 (2)
C6—N1—C7—O12.5 (4)C35—N4—C36—C37−179.78 (19)
N2—N1—C7—C81.7 (2)O4—C36—C37—C401.4 (3)
C6—N1—C7—C8−176.8 (2)N4—C36—C37—C40−178.28 (18)
O1—C7—C8—C11−2.5 (4)O4—C36—C37—C38−178.5 (2)
N1—C7—C8—C11176.71 (19)N4—C36—C37—C381.9 (2)
O1—C7—C8—C9179.0 (2)N4—N5—C38—C370.4 (2)
N1—C7—C8—C9−1.8 (2)N4—N5—C38—C39−177.18 (18)
N1—N2—C9—C8−0.4 (2)C40—C37—C38—N5178.7 (2)
N1—N2—C9—C10177.50 (18)C36—C37—C38—N5−1.4 (2)
C11—C8—C9—N2−176.9 (2)C40—C37—C38—C39−4.1 (4)
C7—C8—C9—N21.4 (2)C36—C37—C38—C39175.8 (2)
C11—C8—C9—C105.5 (4)C48—N6—C40—C37165.84 (19)
C7—C8—C9—C10−176.2 (2)C48—N6—C40—C41−14.5 (3)
C19—N3—C11—C8−174.1 (2)C38—C37—C40—N6173.7 (2)
C19—N3—C11—C124.7 (3)C36—C37—C40—N6−6.1 (3)
C9—C8—C11—N3−176.2 (2)C38—C37—C40—C41−6.0 (4)
C7—C8—C11—N35.8 (3)C36—C37—C40—C41174.20 (18)
C9—C8—C11—C125.0 (4)N6—C40—C41—C42112.5 (2)
C7—C8—C11—C12−173.09 (19)C37—C40—C41—C42−67.8 (3)
N3—C11—C12—C1390.7 (3)N6—C40—C41—C46−65.4 (3)
C8—C11—C12—C13−90.5 (3)C37—C40—C41—C46114.3 (2)
N3—C11—C12—C17−93.4 (3)C46—C41—C42—C430.4 (3)
C8—C11—C12—C1785.4 (3)C40—C41—C42—C43−177.6 (2)
C17—C12—C13—C14−1.9 (3)C41—C42—C43—C440.1 (4)
C11—C12—C13—C14174.0 (2)C42—C43—C44—C45−0.9 (4)
C12—C13—C14—C150.0 (4)C42—C43—C44—C47179.4 (2)
C13—C14—C15—C161.3 (4)C43—C44—C45—C461.3 (4)
C13—C14—C15—C18179.7 (2)C47—C44—C45—C46−179.0 (2)
C14—C15—C16—C17−0.7 (4)C44—C45—C46—C41−0.9 (4)
C18—C15—C16—C17−179.1 (3)C42—C41—C46—C450.0 (3)
C15—C16—C17—C12−1.2 (4)C40—C41—C46—C45178.0 (2)
C13—C12—C17—C162.5 (3)C40—N6—C48—C56134.3 (2)
C11—C12—C17—C16−173.5 (2)C40—N6—C48—C49−106.6 (2)
C11—N3—C19—C27−120.7 (2)N6—C48—C49—C5058.3 (2)
C11—N3—C19—C20119.4 (2)C56—C48—C49—C50178.36 (19)
N3—C19—C20—C21−68.9 (2)C48—C49—C50—C51−95.1 (3)
C27—C19—C20—C21170.4 (2)C48—C49—C50—C5584.4 (3)
C19—C20—C21—C26−94.8 (3)C55—C50—C51—C520.8 (4)
C19—C20—C21—C2284.4 (3)C49—C50—C51—C52−179.7 (3)
C26—C21—C22—C23−0.6 (4)C50—C51—C52—C530.4 (5)
C20—C21—C22—C23−179.8 (2)C51—C52—C53—C54−1.4 (5)
C21—C22—C23—C24−0.2 (4)C52—C53—C54—C551.3 (5)
C22—C23—C24—C250.6 (4)C53—C54—C55—C50−0.2 (5)
C23—C24—C25—C26−0.3 (4)C51—C50—C55—C54−0.9 (4)
C24—C25—C26—C21−0.5 (4)C49—C50—C55—C54179.5 (2)
C22—C21—C26—C251.0 (4)C57—O6—C56—O54.4 (3)
C20—C21—C26—C25−179.9 (2)C57—O6—C56—C48−172.72 (19)
C28—O3—C27—O2−1.8 (4)N6—C48—C56—O521.9 (3)
C28—O3—C27—C19173.7 (2)C49—C48—C56—O5−99.2 (3)
N3—C19—C27—O2−22.5 (3)N6—C48—C56—O6−160.91 (17)
C20—C19—C27—O298.5 (3)C49—C48—C56—O678.0 (2)
N3—C19—C27—O3162.01 (19)C56—O6—C57—C58−171.0 (2)

Hydrogen-bond geometry (Å, °)

Cg6 is the centroid of C30–C35 ring.
D—H···AD—HH···AD···AD—H···A
N3—H3A···O10.862.012.713 (2)138
N6—H6···O40.862.032.698 (2)133
C16—H16···O6i0.932.513.397 (3)161
C28—H28B···O1ii0.972.443.357 (3)157
C45—H45···Cg6iii0.932.773.449 (3)130
C57—H57B···Cg6iv0.962.783.663 (3)152

Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+2, −z+1; (iii) −x, −y+1, −z+2; (iv) x−1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5268).

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