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Acta Crystallogr Sect E Struct Rep Online. 2010 January 1; 66(Pt 1): o145.
Published online 2009 December 16. doi:  10.1107/S1600536809053094
PMCID: PMC2980256

1′-Methyl-2-oxo-5′-phenyl­spiro­[indoline-3,3′-pyrrolidine]-4′,4′-dicarbo­nitrile

Abstract

The title spiro-compound, C20H16N4O, crystallizes with four independent mol­ecules in the asymmetric unit. In all of them, the oxindole unit is planar, the r.m.s. deviations ranging from 0.07 to 0.08 Å, while the pyrrolinyl ring adopts an envelope conformation (with the N atom representing the flap). In the crystal, adjacent mol­ecules are linked by N—H(...)N and N—H(...)O hydrogen bonds.

Related literature

For the synthesis, see: Ghandi et al. (2009 [triangle]).

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Object name is e-66-0o145-scheme1.jpg

Experimental

Crystal data

  • C20H16N4O
  • M r = 328.37
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o145-efi1.jpg
  • a = 14.3750 (3) Å
  • b = 15.8411 (3) Å
  • c = 30.7348 (5) Å
  • β = 101.888 (1)°
  • V = 6848.7 (2) Å3
  • Z = 16
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 295 K
  • 0.20 × 0.15 × 0.05 mm

Data collection

  • Bruker SMART APEX diffractometer
  • 39181 measured reflections
  • 7860 independent reflections
  • 4866 reflections with I > 2σ(I)
  • R int = 0.062

Refinement

  • R[F 2 > 2σ(F 2)] = 0.072
  • wR(F 2) = 0.198
  • S = 1.03
  • 7860 reflections
  • 901 parameters
  • 2 restraints
  • H-atom parameters constrained
  • Δρmax = 0.57 e Å−3
  • Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [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: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809053094/bt5137sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809053094/bt5137Isup2.hkl

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

Acknowledgments

We thank Shahid Beheshti University and the University of Malaya for supporting this study.

supplementary crystallographic information

Experimental

Sarcosine (89 mg,1.0 mmol), benzaldehyde (104 mg, 1.0 mmol) and 2-oxo-(3H)-indol-3-ylidine-malononitrile (195 mg, 1.0 mmol) in dry toluene (30 ml) containing molecular sieves (500 mg,3 Å) were heated for five hours. The solvent was removed under reduced pressure and the residue was subjected to column chromatography on silica gel by using hexane–ethyl acetate (9:1) as eluent to give the product. This was recrystallized from methanol.

Refinement

Due to the absence of anomalous scatterers, Friedel pairs were merged. Hydrogen atoms were placed in calculated positions (C—H 0.93–0.98, N–H 0.86 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5U(C, N).

Figures

Fig. 1.
Anisotropic displacement ellipsoid plot (Barbour, 2001) of one of the four independent molecules of C20H16N4O; ellipsoids are drawn at the 50% probability level and H atoms of arbitrary radius.

Crystal data

C20H16N4OF(000) = 2752
Mr = 328.37Dx = 1.274 Mg m3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 8592 reflections
a = 14.3750 (3) Åθ = 2.1–28.2°
b = 15.8411 (3) ŵ = 0.08 mm1
c = 30.7348 (5) ÅT = 295 K
β = 101.888 (1)°Block, colorless
V = 6848.7 (2) Å30.20 × 0.15 × 0.05 mm
Z = 16

Data collection

Bruker SMART APEX diffractometer4866 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.062
graphiteθmax = 27.5°, θmin = 1.4°
ω scansh = −18→18
39181 measured reflectionsk = −19→20
7860 independent reflectionsl = −39→39

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)] = 0.072Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.198H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.1236P)2] where P = (Fo2 + 2Fc2)/3
7860 reflections(Δ/σ)max = 0.001
901 parametersΔρmax = 0.57 e Å3
2 restraintsΔρmin = −0.25 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
O10.5000 (4)0.4227 (3)0.50000 (15)0.0745 (13)
O20.4094 (3)0.6148 (2)0.39678 (14)0.0600 (11)
O30.4609 (4)0.3302 (3)0.23104 (15)0.0803 (15)
O40.0523 (3)0.6404 (2)0.33482 (15)0.0636 (11)
N10.4163 (4)0.4444 (3)0.42872 (18)0.0458 (12)
H10.41540.49870.42860.055*
N20.4967 (4)0.1845 (3)0.49913 (18)0.0488 (13)
N30.2501 (4)0.3842 (4)0.5061 (2)0.0745 (16)
N40.2459 (4)0.1583 (3)0.4414 (2)0.0672 (17)
N50.3614 (3)0.7448 (3)0.36747 (17)0.0372 (11)
H50.33500.72980.34090.045*
N60.5214 (3)0.6988 (3)0.51471 (15)0.0430 (11)
N70.3036 (5)0.8377 (4)0.5185 (2)0.082 (2)
N80.2140 (4)0.6247 (4)0.43970 (19)0.0704 (16)
N90.5469 (4)0.3105 (3)0.30183 (16)0.0463 (12)
H90.55080.25640.30180.056*
N100.4660 (3)0.5696 (3)0.23200 (18)0.0523 (13)
N110.7072 (5)0.3702 (4)0.2223 (2)0.0810 (18)
N120.7171 (4)0.5954 (4)0.2875 (2)0.0672 (17)
N130.1014 (4)0.5112 (3)0.36387 (18)0.0450 (12)
H130.12940.52690.39010.054*
N14−0.0612 (3)0.5524 (3)0.21707 (16)0.0424 (12)
N150.1564 (5)0.4170 (4)0.2118 (2)0.0767 (19)
N160.2441 (4)0.6315 (4)0.28951 (18)0.0688 (16)
C10.3771 (3)0.3941 (3)0.39179 (17)0.0370 (11)
C20.3392 (4)0.4208 (4)0.3492 (2)0.0464 (15)
H20.33240.47780.34220.056*
C30.3114 (4)0.3591 (4)0.3173 (2)0.0578 (15)
H30.28430.37470.28830.069*
C40.3235 (5)0.2750 (4)0.3280 (2)0.0640 (18)
H40.30530.23470.30590.077*
C50.3618 (4)0.2492 (4)0.3707 (2)0.0449 (15)
H5A0.37050.19220.37740.054*
C60.3872 (4)0.3099 (3)0.4034 (2)0.0390 (12)
C70.4306 (4)0.3034 (3)0.45186 (18)0.0409 (12)
C80.4556 (4)0.3972 (3)0.4645 (2)0.0442 (14)
C90.5172 (4)0.2412 (4)0.4647 (2)0.0542 (17)
H9A0.52540.20910.43890.065*
H9B0.57520.27260.47580.065*
C100.4364 (4)0.2321 (3)0.52346 (18)0.0444 (12)
H100.47380.27810.53980.053*
C110.3635 (4)0.2699 (3)0.48389 (18)0.0411 (12)
C120.5809 (5)0.1476 (5)0.5260 (3)0.070 (2)
H12A0.56330.11210.54830.105*
H12B0.62230.19170.54010.105*
H12C0.61320.11450.50760.105*
C130.3948 (4)0.1791 (4)0.5558 (2)0.0459 (13)
C140.3623 (5)0.0975 (4)0.5459 (2)0.0583 (17)
H140.36680.07310.51890.070*
C150.3227 (5)0.0519 (4)0.5767 (3)0.0604 (18)
H150.2993−0.00230.57010.072*
C160.3192 (6)0.0888 (5)0.6169 (3)0.074 (2)
H160.29310.05850.63740.088*
C170.3521 (5)0.1673 (5)0.6275 (2)0.067 (2)
H170.34960.19020.65500.081*
C180.3904 (5)0.2143 (4)0.5967 (2)0.0583 (16)
H180.41270.26880.60360.070*
C190.3028 (4)0.3354 (4)0.4968 (2)0.0456 (13)
C200.2986 (4)0.2049 (3)0.4606 (2)0.0438 (13)
C210.3701 (4)0.8286 (3)0.38201 (19)0.0398 (12)
C220.3460 (5)0.9015 (4)0.3568 (2)0.0491 (16)
H220.31790.89920.32670.059*
C230.3664 (4)0.9775 (4)0.3790 (3)0.0619 (17)
H230.35091.02760.36340.074*
C240.4092 (5)0.9816 (4)0.4239 (3)0.0642 (18)
H240.42181.03370.43780.077*
C250.4328 (5)0.9084 (4)0.4476 (3)0.0574 (18)
H250.46410.91090.47720.069*
C260.4098 (3)0.8304 (3)0.42720 (19)0.0360 (11)
C270.4273 (3)0.7417 (3)0.44390 (16)0.0390 (11)
C280.3992 (4)0.6902 (3)0.40008 (17)0.0391 (11)
C290.5275 (4)0.7205 (4)0.4685 (2)0.0445 (14)
H29A0.55240.67310.45450.053*
H29B0.56930.76850.46830.053*
C300.4324 (3)0.6537 (3)0.51070 (16)0.0384 (11)
H300.43790.59920.49630.046*
C310.3634 (3)0.7113 (3)0.47756 (16)0.0388 (11)
C320.6039 (5)0.6535 (5)0.5385 (2)0.0609 (18)
H32A0.59560.64040.56790.091*
H32B0.65960.68780.54030.091*
H32C0.61130.60210.52300.091*
C330.3986 (4)0.6381 (4)0.55392 (18)0.0401 (13)
C340.3450 (5)0.5668 (4)0.5557 (2)0.0597 (18)
H340.33470.52840.53230.072*
C350.3062 (6)0.5526 (6)0.5931 (3)0.081 (3)
H350.26660.50660.59440.097*
C360.3282 (6)0.6091 (6)0.6286 (3)0.076 (2)
H360.30580.59820.65430.091*
C370.3791 (6)0.6767 (5)0.6269 (2)0.073 (2)
H370.39080.71390.65080.087*
C380.4162 (5)0.6931 (4)0.5890 (2)0.0545 (16)
H380.45260.74130.58770.065*
C390.3304 (4)0.7836 (4)0.50075 (18)0.0462 (13)
C400.2798 (4)0.6639 (4)0.4556 (2)0.0482 (15)
C410.5833 (3)0.3617 (3)0.33911 (17)0.0387 (11)
C420.6212 (5)0.3355 (4)0.3813 (2)0.0476 (15)
H420.62850.27850.38830.057*
C430.6487 (4)0.3979 (4)0.4138 (2)0.0595 (16)
H430.67520.38220.44280.071*
C440.6370 (4)0.4812 (4)0.4031 (2)0.0628 (17)
H440.65320.52140.42550.075*
C450.6009 (5)0.5082 (4)0.3590 (2)0.0545 (18)
H450.59550.56530.35170.065*
C460.5736 (4)0.4454 (3)0.32667 (19)0.0369 (11)
C470.5280 (4)0.4517 (3)0.27773 (18)0.0412 (12)
C480.5057 (4)0.3566 (4)0.2666 (2)0.0473 (15)
C490.4408 (5)0.5089 (4)0.2629 (3)0.0576 (18)
H49A0.38620.47580.24860.069*
H49B0.42510.53760.28840.069*
C500.5240 (4)0.5239 (3)0.20686 (18)0.0444 (12)
H500.48580.47870.19020.053*
C510.5967 (3)0.4840 (3)0.24662 (18)0.0407 (12)
C520.3795 (5)0.6080 (5)0.2036 (3)0.068 (2)
H52A0.34380.63720.22210.102*
H52B0.34090.56430.18740.102*
H52C0.39830.64710.18320.102*
C530.5665 (4)0.5768 (4)0.1750 (2)0.0469 (15)
C540.5981 (5)0.6575 (4)0.1841 (2)0.0525 (16)
H540.59170.68260.21070.063*
C550.6387 (6)0.7021 (5)0.1550 (3)0.074 (2)
H550.65860.75710.16220.089*
C560.6509 (6)0.6690 (6)0.1164 (3)0.077 (3)
H560.67980.69990.09710.093*
C570.6195 (6)0.5884 (7)0.1065 (3)0.084 (3)
H570.62770.56410.07990.101*
C580.5758 (5)0.5417 (5)0.1349 (2)0.0617 (18)
H580.55320.48770.12710.074*
C590.6572 (4)0.4177 (4)0.2320 (3)0.0554 (16)
C600.6622 (4)0.5478 (4)0.2700 (2)0.0445 (13)
C610.0914 (3)0.4266 (3)0.34933 (19)0.0401 (12)
C620.1147 (5)0.3531 (4)0.3747 (2)0.0506 (17)
H620.14210.35560.40480.061*
C630.0954 (5)0.2774 (4)0.3531 (3)0.0630 (17)
H630.11180.22740.36870.076*
C640.0519 (6)0.2739 (4)0.3086 (3)0.065 (2)
H640.03700.22150.29530.078*
C650.0302 (5)0.3457 (4)0.2836 (2)0.0541 (17)
H650.00250.34280.25350.065*
C660.0512 (4)0.4239 (3)0.30506 (19)0.0400 (12)
C670.0322 (3)0.5126 (3)0.28778 (16)0.0373 (11)
C680.0611 (4)0.5636 (3)0.33100 (17)0.0413 (11)
C69−0.0690 (4)0.5321 (4)0.2623 (2)0.0540 (17)
H69A−0.11000.48360.26250.065*
H69B−0.09530.57950.27570.065*
C700.0253 (3)0.6005 (3)0.22002 (16)0.0382 (11)
H700.01870.65510.23420.046*
C710.0952 (3)0.5429 (3)0.25311 (16)0.0380 (11)
C72−0.1442 (4)0.6002 (4)0.1939 (2)0.0535 (16)
H72A−0.20060.56710.19270.080*
H72B−0.13700.61290.16430.080*
H72C−0.14920.65180.20970.080*
C730.0560 (4)0.6148 (3)0.17656 (18)0.0387 (12)
C740.1120 (4)0.6823 (4)0.1719 (2)0.0543 (16)
H740.12810.72100.19500.065*
C750.1452 (5)0.6936 (5)0.1331 (3)0.070 (2)
H750.18300.74030.13070.084*
C760.1245 (6)0.6395 (6)0.0989 (3)0.078 (2)
H760.14990.64660.07360.093*
C770.0632 (6)0.5718 (5)0.1024 (2)0.0692 (19)
H770.04460.53530.07850.083*
C780.0305 (5)0.5589 (4)0.1408 (2)0.0576 (16)
H78−0.00850.51300.14310.069*
C790.1282 (4)0.4718 (4)0.2300 (2)0.0527 (15)
C800.1817 (4)0.5926 (4)0.27405 (19)0.0483 (14)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.087 (3)0.075 (3)0.055 (3)−0.038 (3)0.000 (2)−0.001 (2)
O20.090 (3)0.034 (2)0.061 (3)0.007 (2)0.027 (2)−0.0034 (18)
O30.106 (4)0.077 (3)0.050 (2)−0.044 (3)−0.003 (2)0.000 (2)
O40.098 (3)0.033 (2)0.066 (3)0.004 (2)0.032 (2)0.0004 (18)
N10.056 (3)0.030 (2)0.054 (3)−0.013 (2)0.017 (2)0.001 (2)
N20.054 (3)0.035 (3)0.067 (3)0.011 (2)0.034 (3)0.017 (2)
N30.067 (3)0.058 (3)0.108 (5)0.015 (3)0.040 (3)0.000 (3)
N40.073 (4)0.046 (3)0.086 (5)−0.019 (3)0.022 (3)−0.001 (3)
N50.042 (3)0.035 (2)0.036 (3)−0.006 (2)0.012 (2)0.003 (2)
N60.031 (2)0.054 (3)0.043 (3)0.0048 (19)0.0055 (19)0.010 (2)
N70.099 (5)0.078 (4)0.076 (4)0.030 (4)0.032 (4)0.001 (3)
N80.052 (3)0.104 (5)0.052 (3)−0.011 (3)0.004 (3)−0.010 (3)
N90.059 (3)0.030 (2)0.051 (3)−0.002 (2)0.014 (2)−0.006 (2)
N100.042 (3)0.057 (3)0.062 (3)0.014 (2)0.021 (2)0.028 (3)
N110.078 (4)0.050 (3)0.124 (5)0.003 (3)0.043 (4)−0.011 (3)
N120.062 (4)0.057 (3)0.087 (5)−0.003 (3)0.025 (3)−0.004 (3)
N130.057 (3)0.036 (3)0.041 (3)−0.004 (2)0.009 (2)−0.003 (2)
N140.039 (3)0.042 (2)0.047 (3)0.002 (2)0.012 (2)0.003 (2)
N150.093 (4)0.069 (4)0.078 (4)0.039 (3)0.040 (4)0.006 (3)
N160.049 (3)0.100 (5)0.056 (3)−0.017 (3)0.009 (3)0.003 (3)
C10.036 (2)0.034 (3)0.046 (3)−0.006 (2)0.021 (2)0.003 (2)
C20.037 (3)0.049 (4)0.055 (4)−0.002 (3)0.014 (3)0.011 (3)
C30.049 (3)0.078 (5)0.047 (3)−0.016 (3)0.012 (2)0.003 (3)
C40.070 (4)0.075 (5)0.053 (4)−0.032 (3)0.027 (3)−0.019 (3)
C50.052 (4)0.033 (3)0.057 (4)−0.008 (3)0.029 (3)−0.002 (3)
C60.037 (3)0.027 (3)0.057 (4)0.001 (2)0.021 (3)−0.004 (3)
C70.040 (3)0.034 (3)0.052 (3)−0.005 (2)0.018 (2)0.003 (2)
C80.047 (3)0.034 (3)0.054 (4)−0.010 (2)0.017 (3)0.004 (3)
C90.036 (3)0.062 (4)0.069 (4)0.006 (3)0.021 (3)0.024 (3)
C100.041 (3)0.046 (3)0.049 (3)0.000 (2)0.017 (2)0.009 (2)
C110.046 (3)0.028 (3)0.051 (3)0.001 (2)0.013 (2)0.009 (2)
C120.064 (4)0.074 (5)0.080 (5)0.023 (4)0.033 (4)0.030 (4)
C130.037 (3)0.048 (3)0.053 (4)0.003 (3)0.011 (2)0.010 (3)
C140.057 (4)0.057 (4)0.067 (4)0.013 (3)0.027 (3)0.015 (3)
C150.052 (4)0.048 (4)0.084 (5)0.006 (3)0.021 (4)0.020 (4)
C160.068 (4)0.074 (5)0.092 (6)0.030 (4)0.049 (4)0.051 (5)
C170.069 (4)0.087 (5)0.053 (4)0.009 (4)0.028 (3)0.028 (4)
C180.057 (4)0.063 (4)0.054 (4)−0.007 (3)0.010 (3)0.009 (3)
C190.048 (3)0.039 (3)0.055 (4)−0.006 (3)0.023 (3)0.003 (3)
C200.041 (3)0.034 (3)0.059 (4)−0.002 (2)0.018 (3)0.008 (3)
C210.038 (3)0.038 (3)0.048 (3)−0.001 (2)0.021 (2)0.003 (2)
C220.042 (3)0.052 (4)0.057 (4)0.006 (3)0.017 (3)0.015 (3)
C230.062 (4)0.034 (3)0.098 (5)0.010 (3)0.037 (4)0.020 (3)
C240.077 (4)0.035 (3)0.088 (5)−0.005 (3)0.037 (4)−0.009 (4)
C250.056 (4)0.044 (4)0.073 (5)−0.011 (3)0.015 (3)−0.019 (3)
C260.033 (2)0.031 (3)0.047 (3)0.002 (2)0.015 (2)−0.001 (2)
C270.040 (3)0.043 (3)0.037 (3)0.005 (2)0.015 (2)0.002 (2)
C280.047 (3)0.034 (3)0.041 (3)−0.001 (2)0.018 (2)0.001 (2)
C290.037 (3)0.050 (4)0.051 (4)0.004 (2)0.020 (3)0.007 (3)
C300.038 (3)0.039 (3)0.037 (3)0.002 (2)0.005 (2)0.000 (2)
C310.035 (2)0.046 (3)0.036 (3)0.001 (2)0.009 (2)0.004 (2)
C320.041 (3)0.076 (4)0.062 (4)0.020 (3)0.003 (3)0.012 (3)
C330.038 (3)0.048 (3)0.033 (3)0.001 (3)0.002 (2)0.007 (3)
C340.072 (4)0.046 (4)0.057 (4)−0.009 (3)0.004 (3)0.004 (3)
C350.064 (4)0.086 (6)0.088 (6)−0.026 (4)0.004 (4)0.045 (5)
C360.079 (5)0.100 (6)0.054 (4)0.021 (5)0.025 (4)0.027 (4)
C370.107 (6)0.072 (5)0.037 (4)0.018 (4)0.011 (4)0.004 (3)
C380.070 (4)0.050 (4)0.039 (3)−0.010 (3)0.002 (3)−0.002 (3)
C390.048 (3)0.056 (4)0.039 (3)0.009 (3)0.018 (2)0.004 (3)
C400.037 (3)0.067 (4)0.043 (3)0.002 (3)0.013 (3)0.008 (3)
C410.036 (2)0.041 (3)0.040 (3)0.002 (2)0.012 (2)0.002 (2)
C420.046 (3)0.044 (3)0.054 (4)−0.003 (3)0.013 (3)0.010 (3)
C430.053 (3)0.079 (5)0.048 (3)−0.015 (3)0.014 (3)0.005 (3)
C440.072 (4)0.069 (4)0.052 (4)−0.025 (3)0.023 (3)−0.022 (3)
C450.072 (5)0.036 (3)0.063 (5)−0.012 (3)0.030 (4)−0.010 (3)
C460.042 (3)0.026 (2)0.048 (3)−0.008 (2)0.023 (2)0.000 (2)
C470.038 (3)0.039 (3)0.049 (3)0.004 (2)0.015 (2)0.015 (2)
C480.051 (3)0.049 (3)0.045 (3)−0.016 (3)0.017 (3)−0.003 (3)
C490.048 (4)0.058 (4)0.073 (5)0.007 (3)0.026 (3)0.022 (3)
C500.041 (3)0.042 (3)0.052 (3)0.001 (2)0.012 (2)0.007 (2)
C510.037 (3)0.038 (3)0.050 (3)−0.003 (2)0.014 (2)0.004 (2)
C520.049 (4)0.079 (5)0.078 (5)0.021 (3)0.019 (3)0.040 (4)
C530.042 (3)0.057 (4)0.044 (3)0.000 (3)0.015 (2)0.014 (3)
C540.061 (4)0.041 (3)0.059 (4)0.009 (3)0.017 (3)0.011 (3)
C550.069 (5)0.054 (4)0.098 (7)0.005 (3)0.015 (4)0.031 (4)
C560.054 (4)0.101 (7)0.077 (6)0.006 (4)0.016 (4)0.056 (5)
C570.083 (5)0.126 (8)0.043 (4)0.044 (6)0.011 (4)0.010 (4)
C580.070 (4)0.073 (4)0.042 (4)0.005 (3)0.011 (3)0.002 (3)
C590.047 (3)0.031 (3)0.091 (5)0.000 (3)0.021 (3)0.002 (3)
C600.046 (3)0.039 (3)0.053 (3)0.005 (3)0.021 (3)0.008 (3)
C610.031 (2)0.039 (3)0.052 (3)−0.001 (2)0.011 (2)0.002 (3)
C620.050 (3)0.045 (4)0.062 (4)0.004 (3)0.024 (3)0.019 (3)
C630.067 (4)0.043 (4)0.087 (5)0.012 (3)0.035 (4)0.018 (3)
C640.077 (4)0.039 (4)0.088 (6)−0.006 (3)0.037 (4)−0.007 (4)
C650.068 (4)0.043 (4)0.060 (4)−0.011 (3)0.033 (3)−0.015 (3)
C660.041 (3)0.039 (3)0.044 (3)0.003 (2)0.019 (2)0.001 (2)
C670.035 (2)0.037 (3)0.042 (3)0.004 (2)0.011 (2)0.002 (2)
C680.052 (3)0.032 (3)0.044 (3)0.003 (2)0.020 (2)0.002 (2)
C690.039 (3)0.075 (5)0.050 (4)0.007 (3)0.013 (3)0.018 (3)
C700.036 (2)0.034 (3)0.043 (3)0.001 (2)0.005 (2)−0.003 (2)
C710.036 (3)0.042 (3)0.037 (3)0.004 (2)0.010 (2)0.002 (2)
C720.036 (3)0.062 (4)0.060 (4)0.006 (3)0.004 (3)0.012 (3)
C730.036 (3)0.041 (3)0.040 (3)0.002 (2)0.008 (2)0.007 (2)
C740.045 (3)0.061 (4)0.053 (4)0.002 (3)0.001 (3)0.002 (3)
C750.054 (4)0.078 (5)0.079 (6)−0.006 (3)0.017 (4)0.032 (4)
C760.079 (5)0.104 (6)0.063 (5)0.029 (5)0.043 (4)0.029 (4)
C770.096 (5)0.073 (4)0.046 (4)0.004 (4)0.033 (4)−0.004 (3)
C780.078 (4)0.051 (3)0.045 (3)−0.005 (3)0.016 (3)−0.004 (3)
C790.056 (4)0.051 (4)0.051 (3)0.016 (3)0.011 (3)0.008 (3)
C800.041 (3)0.068 (4)0.037 (3)−0.001 (3)0.010 (3)0.004 (3)

Geometric parameters (Å, °)

O1—C81.215 (7)C30—C311.561 (7)
O2—C281.209 (6)C30—H300.9800
O3—C481.223 (7)C31—C401.459 (8)
O4—C681.232 (6)C31—C391.477 (8)
N1—C81.352 (8)C32—H32A0.9600
N1—C11.406 (7)C32—H32B0.9600
N1—H10.8600C32—H32C0.9600
N2—C121.441 (8)C33—C381.370 (8)
N2—C91.464 (8)C33—C341.375 (9)
N2—C101.465 (7)C34—C351.396 (11)
N3—C191.160 (7)C34—H340.9300
N4—C201.133 (7)C35—C361.395 (13)
N5—C281.350 (7)C35—H350.9300
N5—C211.399 (7)C36—C371.304 (11)
N5—H50.8600C36—H360.9300
N6—C301.449 (7)C37—C381.400 (10)
N6—C321.450 (7)C37—H370.9300
N6—C291.480 (8)C38—H380.9300
N7—C391.125 (8)C41—C421.364 (8)
N8—C401.153 (8)C41—C461.379 (7)
N9—C481.338 (8)C42—C431.401 (9)
N9—C411.413 (7)C42—H420.9300
N9—H90.8600C43—C441.361 (9)
N10—C501.443 (7)C43—H430.9300
N10—C491.450 (8)C44—C451.415 (10)
N10—C521.492 (8)C44—H440.9300
N11—C591.121 (8)C45—C461.405 (9)
N12—C601.142 (8)C45—H450.9300
N13—C681.344 (7)C46—C471.515 (8)
N13—C611.410 (7)C47—C491.538 (8)
N13—H130.8600C47—C481.563 (8)
N14—C701.445 (6)C47—C511.594 (7)
N14—C691.452 (8)C49—H49A0.9700
N14—C721.467 (7)C49—H49B0.9700
N15—C791.152 (8)C50—C531.510 (8)
N16—C801.111 (8)C50—C511.568 (7)
C1—C21.376 (8)C50—H500.9800
C1—C61.380 (7)C51—C601.466 (8)
C2—C31.384 (9)C51—C591.492 (9)
C2—H20.9300C52—H52A0.9600
C3—C41.374 (9)C52—H52B0.9600
C3—H30.9300C52—H52C0.9600
C4—C51.375 (9)C53—C541.366 (8)
C4—H40.9300C53—C581.384 (9)
C5—C61.384 (8)C54—C551.362 (10)
C5—H5A0.9300C54—H540.9300
C6—C71.496 (8)C55—C561.341 (13)
C7—C81.560 (8)C55—H550.9300
C7—C91.572 (8)C56—C571.369 (12)
C7—C111.604 (7)C56—H560.9300
C9—H9A0.9700C57—C581.390 (12)
C9—H9B0.9700C57—H570.9300
C10—C131.515 (7)C58—H580.9300
C10—C111.553 (7)C61—C661.365 (8)
C10—H100.9800C61—C621.403 (8)
C11—C191.461 (8)C62—C631.371 (10)
C11—C201.472 (8)C62—H620.9300
C12—H12A0.9600C63—C641.385 (10)
C12—H12B0.9600C63—H630.9300
C12—H12C0.9600C64—C651.372 (10)
C13—C141.387 (9)C64—H640.9300
C13—C181.387 (9)C65—C661.407 (8)
C14—C151.400 (9)C65—H650.9300
C14—H140.9300C66—C671.507 (7)
C15—C161.378 (11)C67—C691.536 (7)
C15—H150.9300C67—C681.537 (7)
C16—C171.346 (11)C67—C711.607 (7)
C16—H160.9300C69—H69A0.9700
C17—C181.403 (9)C69—H69B0.9700
C17—H170.9300C70—C731.508 (7)
C18—H180.9300C70—C711.568 (7)
C21—C261.389 (8)C70—H700.9800
C21—C221.395 (8)C71—C791.461 (8)
C22—C231.385 (10)C71—C801.500 (8)
C22—H220.9300C72—H72A0.9600
C23—C241.391 (10)C72—H72B0.9600
C23—H230.9300C72—H72C0.9600
C24—C251.375 (10)C73—C741.363 (8)
C24—H240.9300C73—C781.400 (8)
C25—C261.393 (8)C74—C751.383 (10)
C25—H250.9300C74—H740.9300
C26—C271.499 (7)C75—C761.341 (12)
C27—C291.520 (8)C75—H750.9300
C27—C281.555 (7)C76—C771.408 (11)
C27—C311.593 (7)C76—H760.9300
C29—H29A0.9700C77—C781.371 (9)
C29—H29B0.9700C77—H770.9300
C30—C331.525 (8)C78—H780.9300
C8—N1—C1111.9 (4)C34—C35—H35120.8
C8—N1—H1124.0C37—C36—C35122.3 (8)
C1—N1—H1124.0C37—C36—H36118.8
C12—N2—C9113.2 (5)C35—C36—H36118.8
C12—N2—C10115.5 (5)C36—C37—C38119.9 (7)
C9—N2—C10106.3 (4)C36—C37—H37120.0
C28—N5—C21112.0 (5)C38—C37—H37120.0
C28—N5—H5124.0C33—C38—C37119.7 (7)
C21—N5—H5124.0C33—C38—H38120.1
C30—N6—C32114.5 (5)C37—C38—H38120.1
C30—N6—C29105.0 (4)N7—C39—C31178.6 (7)
C32—N6—C29113.2 (5)N8—C40—C31177.4 (7)
C48—N9—C41111.8 (5)C42—C41—C46123.6 (5)
C48—N9—H9124.1C42—C41—N9127.3 (5)
C41—N9—H9124.1C46—C41—N9109.1 (5)
C50—N10—C49105.6 (5)C41—C42—C43117.5 (6)
C50—N10—C52113.3 (5)C41—C42—H42121.3
C49—N10—C52111.2 (5)C43—C42—H42121.3
C68—N13—C61110.5 (5)C44—C43—C42120.6 (6)
C68—N13—H13124.8C44—C43—H43119.7
C61—N13—H13124.8C42—C43—H43119.7
C70—N14—C69107.0 (4)C43—C44—C45121.8 (6)
C70—N14—C72111.2 (4)C43—C44—H44119.1
C69—N14—C72111.2 (5)C45—C44—H44119.1
C2—C1—C6122.8 (5)C46—C45—C44117.2 (6)
C2—C1—N1127.5 (5)C46—C45—H45121.4
C6—C1—N1109.6 (5)C44—C45—H45121.4
C1—C2—C3117.2 (6)C41—C46—C45119.2 (6)
C1—C2—H2121.4C41—C46—C47109.7 (5)
C3—C2—H2121.4C45—C46—C47131.0 (5)
C4—C3—C2120.7 (6)C46—C47—C49119.5 (5)
C4—C3—H3119.7C46—C47—C48100.4 (4)
C2—C3—H3119.7C49—C47—C48112.7 (5)
C3—C4—C5121.5 (6)C46—C47—C51115.0 (4)
C3—C4—H4119.2C49—C47—C51101.6 (4)
C5—C4—H4119.2C48—C47—C51107.6 (5)
C4—C5—C6118.7 (6)O3—C48—N9126.9 (6)
C4—C5—H5A120.7O3—C48—C47124.9 (5)
C6—C5—H5A120.7N9—C48—C47108.2 (5)
C1—C6—C5119.1 (6)N10—C49—C47106.6 (5)
C1—C6—C7108.9 (5)N10—C49—H49A110.4
C5—C6—C7132.0 (5)C47—C49—H49A110.4
C6—C7—C8102.0 (4)N10—C49—H49B110.4
C6—C7—C9116.1 (5)C47—C49—H49B110.4
C8—C7—C9113.9 (5)H49A—C49—H49B108.6
C6—C7—C11117.0 (4)N10—C50—C53115.1 (4)
C8—C7—C11107.4 (4)N10—C50—C5198.7 (4)
C9—C7—C11100.6 (4)C53—C50—C51115.7 (4)
O1—C8—N1127.0 (5)N10—C50—H50108.9
O1—C8—C7126.2 (5)C53—C50—H50108.9
N1—C8—C7106.8 (5)C51—C50—H50108.9
N2—C9—C7107.4 (5)C60—C51—C59106.1 (4)
N2—C9—H9A110.2C60—C51—C50111.2 (4)
C7—C9—H9A110.2C59—C51—C50112.6 (5)
N2—C9—H9B110.2C60—C51—C47110.0 (5)
C7—C9—H9B110.2C59—C51—C47115.3 (4)
H9A—C9—H9B108.5C50—C51—C47101.6 (4)
N2—C10—C13113.9 (4)N10—C52—H52A109.5
N2—C10—C11100.0 (4)N10—C52—H52B109.5
C13—C10—C11115.7 (4)H52A—C52—H52B109.5
N2—C10—H10109.0N10—C52—H52C109.5
C13—C10—H10109.0H52A—C52—H52C109.5
C11—C10—H10109.0H52B—C52—H52C109.5
C19—C11—C20105.9 (4)C54—C53—C58118.0 (6)
C19—C11—C10113.9 (5)C54—C53—C50123.3 (6)
C20—C11—C10111.6 (4)C58—C53—C50118.7 (6)
C19—C11—C7113.6 (4)C55—C54—C53121.3 (7)
C20—C11—C7109.5 (5)C55—C54—H54119.3
C10—C11—C7102.4 (4)C53—C54—H54119.3
N2—C12—H12A109.5C56—C55—C54122.1 (8)
N2—C12—H12B109.5C56—C55—H55119.0
H12A—C12—H12B109.5C54—C55—H55119.0
N2—C12—H12C109.5C55—C56—C57117.7 (7)
H12A—C12—H12C109.5C55—C56—H56121.1
H12B—C12—H12C109.5C57—C56—H56121.1
C14—C13—C18119.8 (6)C56—C57—C58121.8 (8)
C14—C13—C10122.2 (6)C56—C57—H57119.1
C18—C13—C10118.0 (5)C58—C57—H57119.1
C13—C14—C15119.9 (7)C53—C58—C57119.1 (7)
C13—C14—H14120.1C53—C58—H58120.4
C15—C14—H14120.1C57—C58—H58120.4
C16—C15—C14118.9 (7)N11—C59—C51176.0 (7)
C16—C15—H15120.6N12—C60—C51176.3 (6)
C14—C15—H15120.6C66—C61—C62122.1 (5)
C17—C16—C15122.1 (7)C66—C61—N13109.9 (5)
C17—C16—H16119.0C62—C61—N13128.0 (6)
C15—C16—H16119.0C63—C62—C61117.2 (6)
C16—C17—C18119.7 (7)C63—C62—H62121.4
C16—C17—H17120.1C61—C62—H62121.4
C18—C17—H17120.1C62—C63—C64121.2 (6)
C13—C18—C17119.6 (7)C62—C63—H63119.4
C13—C18—H18120.2C64—C63—H63119.4
C17—C18—H18120.2C65—C64—C63121.6 (6)
N3—C19—C11175.9 (6)C65—C64—H64119.2
N4—C20—C11176.2 (6)C63—C64—H64119.2
C26—C21—C22122.9 (5)C64—C65—C66117.8 (7)
C26—C21—N5109.3 (5)C64—C65—H65121.1
C22—C21—N5127.8 (6)C66—C65—H65121.1
C23—C22—C21116.2 (6)C61—C66—C65120.0 (5)
C23—C22—H22121.9C61—C66—C67109.3 (5)
C21—C22—H22121.9C65—C66—C67130.5 (5)
C22—C23—C24122.3 (6)C66—C67—C69116.8 (5)
C22—C23—H23118.8C66—C67—C68100.9 (4)
C24—C23—H23118.8C69—C67—C68113.2 (5)
C25—C24—C23119.8 (6)C66—C67—C71115.2 (4)
C25—C24—H24120.1C69—C67—C71101.9 (4)
C23—C24—H24120.1C68—C67—C71109.1 (4)
C24—C25—C26120.0 (7)O4—C68—N13125.2 (5)
C24—C25—H25120.0O4—C68—C67125.9 (5)
C26—C25—H25120.0N13—C68—C67108.8 (4)
C21—C26—C25118.6 (5)N14—C69—C67106.3 (5)
C21—C26—C27109.2 (4)N14—C69—H69A110.5
C25—C26—C27132.0 (6)C67—C69—H69A110.5
C26—C27—C29116.9 (5)N14—C69—H69B110.5
C26—C27—C28101.6 (4)C67—C69—H69B110.5
C29—C27—C28111.4 (4)H69A—C69—H69B108.7
C26—C27—C31115.3 (4)N14—C70—C73115.4 (4)
C29—C27—C31102.9 (4)N14—C70—C7199.3 (4)
C28—C27—C31108.8 (4)C73—C70—C71113.4 (4)
O2—C28—N5127.4 (5)N14—C70—H70109.5
O2—C28—C27125.2 (5)C73—C70—H70109.5
N5—C28—C27107.4 (4)C71—C70—H70109.5
N6—C29—C27106.9 (4)C79—C71—C80106.9 (5)
N6—C29—H29A110.3C79—C71—C70111.3 (4)
C27—C29—H29A110.3C80—C71—C70109.6 (4)
N6—C29—H29B110.3C79—C71—C67112.1 (4)
C27—C29—H29B110.3C80—C71—C67113.7 (4)
H29A—C29—H29B108.6C70—C71—C67103.3 (4)
N6—C30—C33116.1 (4)N14—C72—H72A109.5
N6—C30—C31101.4 (4)N14—C72—H72B109.5
C33—C30—C31112.9 (4)H72A—C72—H72B109.5
N6—C30—H30108.7N14—C72—H72C109.5
C33—C30—H30108.7H72A—C72—H72C109.5
C31—C30—H30108.7H72B—C72—H72C109.5
C40—C31—C39107.8 (4)C74—C73—C78118.5 (6)
C40—C31—C30110.6 (5)C74—C73—C70119.9 (5)
C39—C31—C30111.3 (4)C78—C73—C70121.6 (5)
C40—C31—C27112.7 (4)C73—C74—C75120.6 (7)
C39—C31—C27111.4 (4)C73—C74—H74119.7
C30—C31—C27103.1 (4)C75—C74—H74119.7
N6—C32—H32A109.5C76—C75—C74122.2 (7)
N6—C32—H32B109.5C76—C75—H75118.9
H32A—C32—H32B109.5C74—C75—H75118.9
N6—C32—H32C109.5C75—C76—C77117.8 (7)
H32A—C32—H32C109.5C75—C76—H76121.1
H32B—C32—H32C109.5C77—C76—H76121.1
C38—C33—C34120.4 (6)C78—C77—C76120.7 (7)
C38—C33—C30122.9 (5)C78—C77—H77119.6
C34—C33—C30116.7 (5)C76—C77—H77119.6
C33—C34—C35119.1 (7)C77—C78—C73120.0 (6)
C33—C34—H34120.4C77—C78—H78120.0
C35—C34—H34120.4C73—C78—H78120.0
C36—C35—C34118.4 (7)N15—C79—C71178.2 (7)
C36—C35—H35120.8N16—C80—C71178.0 (7)
C8—N1—C1—C2−173.9 (6)C48—N9—C41—C42173.2 (6)
C8—N1—C1—C62.2 (7)C48—N9—C41—C46−5.9 (7)
C6—C1—C2—C3−0.6 (8)C46—C41—C42—C432.1 (9)
N1—C1—C2—C3175.0 (5)N9—C41—C42—C43−176.8 (5)
C1—C2—C3—C4−1.2 (9)C41—C42—C43—C440.4 (9)
C2—C3—C4—C51.1 (9)C42—C43—C44—C45−2.8 (9)
C3—C4—C5—C61.0 (9)C43—C44—C45—C462.6 (10)
C2—C1—C6—C52.7 (8)C42—C41—C46—C45−2.1 (8)
N1—C1—C6—C5−173.7 (5)N9—C41—C46—C45176.9 (5)
C2—C1—C6—C7180.0 (5)C42—C41—C46—C47−179.3 (5)
N1—C1—C6—C73.6 (6)N9—C41—C46—C47−0.3 (6)
C4—C5—C6—C1−2.8 (8)C44—C45—C46—C41−0.2 (9)
C4—C5—C6—C7−179.3 (6)C44—C45—C46—C47176.3 (6)
C1—C6—C7—C8−7.1 (5)C41—C46—C47—C49128.8 (5)
C5—C6—C7—C8169.7 (6)C45—C46—C47—C49−48.0 (8)
C1—C6—C7—C9−131.5 (5)C41—C46—C47—C485.1 (5)
C5—C6—C7—C945.3 (8)C45—C46—C47—C48−171.6 (6)
C1—C6—C7—C11109.8 (5)C41—C46—C47—C51−110.0 (5)
C5—C6—C7—C11−73.4 (8)C45—C46—C47—C5173.2 (7)
C1—N1—C8—O1174.8 (6)C41—N9—C48—O3−173.2 (6)
C1—N1—C8—C7−6.7 (7)C41—N9—C48—C479.2 (7)
C6—C7—C8—O1−173.3 (6)C46—C47—C48—O3173.8 (6)
C9—C7—C8—O1−47.4 (8)C49—C47—C48—O345.6 (9)
C11—C7—C8—O163.1 (8)C51—C47—C48—O3−65.6 (8)
C6—C7—C8—N18.3 (6)C46—C47—C48—N9−8.5 (6)
C9—C7—C8—N1134.1 (5)C49—C47—C48—N9−136.7 (6)
C11—C7—C8—N1−115.4 (5)C51—C47—C48—N9112.0 (5)
C12—N2—C9—C7−157.0 (5)C50—N10—C49—C4736.7 (7)
C10—N2—C9—C7−29.2 (7)C52—N10—C49—C47159.9 (6)
C6—C7—C9—N2−127.9 (6)C46—C47—C49—N10121.7 (6)
C8—C7—C9—N2114.0 (6)C48—C47—C49—N10−120.8 (6)
C11—C7—C9—N2−0.6 (6)C51—C47—C49—N10−5.9 (7)
C12—N2—C10—C13−62.9 (7)C49—N10—C50—C53−174.6 (5)
C9—N2—C10—C13170.7 (5)C52—N10—C50—C5363.5 (6)
C12—N2—C10—C11173.1 (5)C49—N10—C50—C51−50.8 (5)
C9—N2—C10—C1146.7 (5)C52—N10—C50—C51−172.7 (5)
N2—C10—C11—C19−168.5 (4)N10—C50—C51—C60−72.3 (5)
C13—C10—C11—C1968.7 (6)C53—C50—C51—C6051.0 (7)
N2—C10—C11—C2071.5 (5)N10—C50—C51—C59168.7 (4)
C13—C10—C11—C20−51.2 (6)C53—C50—C51—C59−68.0 (6)
N2—C10—C11—C7−45.5 (5)N10—C50—C51—C4744.7 (5)
C13—C10—C11—C7−168.3 (4)C53—C50—C51—C47168.1 (5)
C6—C7—C11—C19−82.2 (6)C46—C47—C51—C60−36.1 (6)
C8—C7—C11—C1931.7 (6)C49—C47—C51—C6094.4 (5)
C9—C7—C11—C19151.1 (5)C48—C47—C51—C60−147.0 (5)
C6—C7—C11—C2036.0 (6)C46—C47—C51—C5983.9 (6)
C8—C7—C11—C20149.9 (4)C49—C47—C51—C59−145.6 (5)
C9—C7—C11—C20−90.8 (5)C48—C47—C51—C59−27.0 (6)
C6—C7—C11—C10154.5 (5)C46—C47—C51—C50−154.0 (4)
C8—C7—C11—C10−91.6 (5)C49—C47—C51—C50−23.5 (6)
C9—C7—C11—C1027.8 (5)C48—C47—C51—C5095.1 (5)
N2—C10—C13—C14−39.1 (7)N10—C50—C53—C5436.5 (8)
C11—C10—C13—C1475.9 (7)C51—C50—C53—C54−77.7 (7)
N2—C10—C13—C18140.2 (5)N10—C50—C53—C58−144.6 (6)
C11—C10—C13—C18−104.7 (6)C51—C50—C53—C58101.1 (6)
C18—C13—C14—C151.9 (9)C58—C53—C54—C55−0.9 (10)
C10—C13—C14—C15−178.8 (5)C50—C53—C54—C55177.9 (6)
C13—C14—C15—C16−1.6 (10)C53—C54—C55—C56−0.8 (11)
C14—C15—C16—C170.3 (11)C54—C55—C56—C571.1 (12)
C15—C16—C17—C180.9 (11)C55—C56—C57—C580.4 (12)
C14—C13—C18—C17−0.7 (9)C54—C53—C58—C572.3 (9)
C10—C13—C18—C17179.9 (5)C50—C53—C58—C57−176.6 (6)
C16—C17—C18—C13−0.7 (10)C56—C57—C58—C53−2.1 (11)
C28—N5—C21—C26−4.2 (6)C68—N13—C61—C665.4 (7)
C28—N5—C21—C22174.6 (5)C68—N13—C61—C62−172.8 (6)
C26—C21—C22—C231.8 (9)C66—C61—C62—C63−0.1 (9)
N5—C21—C22—C23−176.9 (5)N13—C61—C62—C63177.9 (6)
C21—C22—C23—C240.5 (10)C61—C62—C63—C64−2.0 (10)
C22—C23—C24—C250.1 (11)C62—C63—C64—C653.0 (11)
C23—C24—C25—C26−3.0 (11)C63—C64—C65—C66−1.8 (10)
C22—C21—C26—C25−4.6 (8)C62—C61—C66—C651.3 (8)
N5—C21—C26—C25174.2 (5)N13—C61—C66—C65−177.1 (5)
C22—C21—C26—C27−179.7 (5)C62—C61—C66—C67178.4 (5)
N5—C21—C26—C27−0.9 (6)N13—C61—C66—C670.0 (6)
C24—C25—C26—C215.1 (9)C64—C65—C66—C61−0.3 (9)
C24—C25—C26—C27178.9 (6)C64—C65—C66—C67−176.7 (6)
C21—C26—C27—C29126.2 (5)C61—C66—C67—C69−127.7 (5)
C25—C26—C27—C29−48.0 (8)C65—C66—C67—C6949.0 (8)
C21—C26—C27—C284.7 (5)C61—C66—C67—C68−4.5 (5)
C25—C26—C27—C28−169.5 (6)C65—C66—C67—C68172.2 (6)
C21—C26—C27—C31−112.7 (5)C61—C66—C67—C71112.8 (5)
C25—C26—C27—C3173.1 (7)C65—C66—C67—C71−70.5 (7)
C21—N5—C28—O2−173.5 (5)C61—N13—C68—O4174.1 (5)
C21—N5—C28—C277.2 (6)C61—N13—C68—C67−8.3 (6)
C26—C27—C28—O2173.5 (5)C66—C67—C68—O4−174.7 (5)
C29—C27—C28—O248.3 (7)C69—C67—C68—O4−49.1 (7)
C31—C27—C28—O2−64.5 (6)C71—C67—C68—O463.6 (6)
C26—C27—C28—N5−7.1 (5)C66—C67—C68—N137.7 (5)
C29—C27—C28—N5−132.3 (5)C69—C67—C68—N13133.4 (5)
C31—C27—C28—N5114.9 (4)C71—C67—C68—N13−113.9 (5)
C30—N6—C29—C2737.0 (6)C70—N14—C69—C67−38.3 (6)
C32—N6—C29—C27162.6 (5)C72—N14—C69—C67−159.9 (5)
C26—C27—C29—N6116.1 (5)C66—C67—C69—N14−115.8 (5)
C28—C27—C29—N6−127.8 (5)C68—C67—C69—N14127.7 (5)
C31—C27—C29—N6−11.4 (6)C71—C67—C69—N1410.7 (6)
C32—N6—C30—C3366.4 (6)C69—N14—C70—C73169.6 (4)
C29—N6—C30—C33−168.8 (4)C72—N14—C70—C73−68.8 (6)
C32—N6—C30—C31−170.8 (5)C69—N14—C70—C7148.1 (5)
C29—N6—C30—C31−46.1 (5)C72—N14—C70—C71169.7 (5)
N6—C30—C31—C40158.4 (4)N14—C70—C71—C7981.6 (5)
C33—C30—C31—C40−76.7 (6)C73—C70—C71—C79−41.4 (6)
N6—C30—C31—C39−81.9 (5)N14—C70—C71—C80−160.4 (4)
C33—C30—C31—C3943.0 (6)C73—C70—C71—C8076.6 (5)
N6—C30—C31—C2737.7 (5)N14—C70—C71—C67−38.9 (5)
C33—C30—C31—C27162.5 (4)C73—C70—C71—C67−161.8 (4)
C26—C27—C31—C4096.6 (6)C66—C67—C71—C7924.9 (6)
C29—C27—C31—C40−135.0 (5)C69—C67—C71—C79−102.6 (5)
C28—C27—C31—C40−16.7 (6)C68—C67—C71—C79137.4 (5)
C26—C27—C31—C39−24.7 (6)C66—C67—C71—C80−96.5 (6)
C29—C27—C31—C39103.7 (5)C69—C67—C71—C80136.0 (5)
C28—C27—C31—C39−138.0 (4)C68—C67—C71—C8016.0 (6)
C26—C27—C31—C30−144.1 (4)C66—C67—C71—C70144.8 (4)
C29—C27—C31—C30−15.7 (5)C69—C67—C71—C7017.3 (5)
C28—C27—C31—C30102.6 (4)C68—C67—C71—C70−102.7 (4)
N6—C30—C33—C3832.4 (7)N14—C70—C73—C74155.5 (5)
C31—C30—C33—C38−84.0 (6)C71—C70—C73—C74−91.0 (6)
N6—C30—C33—C34−150.3 (5)N14—C70—C73—C78−26.4 (7)
C31—C30—C33—C3493.2 (6)C71—C70—C73—C7887.2 (6)
C38—C33—C34—C352.1 (10)C78—C73—C74—C75−1.9 (9)
C30—C33—C34—C35−175.3 (6)C70—C73—C74—C75176.3 (5)
C33—C34—C35—C36−3.8 (11)C73—C74—C75—C76−0.3 (11)
C34—C35—C36—C373.9 (12)C74—C75—C76—C773.2 (11)
C35—C36—C37—C38−2.0 (12)C75—C76—C77—C78−3.9 (11)
C34—C33—C38—C37−0.1 (10)C76—C77—C78—C731.8 (11)
C30—C33—C38—C37177.0 (6)C74—C73—C78—C771.1 (9)
C36—C37—C38—C330.1 (11)C70—C73—C78—C77−177.1 (6)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···O20.862.082.867 (6)153
N5—H5···N160.862.403.184 (8)151
N9—H9···O4i0.862.102.874 (6)150
N13—H13···N80.862.333.120 (8)152

Symmetry codes: (i) x+1/2, y−1/2, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5137).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2009). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Ghandi, M., Yari, A., Tabatabaei Rezaei, A. & Taheri, A. (2009). Tetrahedron Lett.50, 4724–4726.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2009). publCIF In preparation.

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