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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 1| January 2012| Pages o158-o159
doi:10.1107/S1600536811053220

3,3′-Bis(quinolin-8-yl)-1,1′-[4,4′-methyl­enebis(4,1-phenyl­ene)]diurea

Avijit Pramanik,a Tiffany H. Russ,a Douglas R. Powellb and Md. Alamgir Hossaina*

aDepartment of Chemistry and Biochemistry, 1400 J. R. Lynch St, PO Box 17910, Jackson State University, Jackson, MS 39217-0510, USA, and bDepartment of Chemistry and Biochemistry, University of Oklahoma, 620 Parrington Oval, Room 208, Norman, OK 73019-3051, USA
*Correspondence e-mail: alamgir.hossain@jsums.edu

(Received 30 November 2011; accepted 10 December 2011; online 17 December 2011)

The title compound, C33H26N6O2, contains two 3-(quinolin-8-yl)urea groups linked to a diphenyl­methane. The asymmetric unit contains two mol­ecules, A and B. Each quinoline plane is essentially parallel to the attached urea unit [dihedral angles = 8.97 (18) and 8.81 (19) in molecule A and 18.47 (18) and 4.09 (19)° in molecule B]. The two benzene rings are twisted, making dihedral angles of 81.36 (8)° in A and 87.20 (9)° in B. The molecular structures are stabilized by intramolecular N—H⋯N hydrogen bonds. In the crystal, each urea O atom is involved in two N—H⋯O hydrogen bonds, generating two inter­penetrating three-dimensional sets of mol­ecules.

Related literature

For general background to urea-based compounds in supra­molecular chemistry, see: Fan et al. (1993[Fan, E., Van Arman, S. A., Kincaid, S. & Hamilton, A. D. (1993). J. Am. Chem. Soc. 115, 369-370.]); Smith et al. (1992[Smith, P. J., Reddington, M. V. & Wilcox, C. S. (1992). Tetrahedron Lett. 33, 6085-6088.]); Pramanik et al. (2011[Pramanik, A., Thompson, B., Hayes, T., Tucker, K., Powell, D. R., Bonnesen, P. V., Ellis, E. D., Lee, K. S., Yu, H. & Hossain, M. A. (2011). Org. Biomol. Chem. 9, 4444-4447.]); Caltagirone et al. (2008[Caltagirone, C., Hiscock, J. R., Hursthouse, M. B., Light, M. E. & Gale, P. A. (2008). Chem. Eur. J. 14, 10236-10243.]); Custelcean et al. (2005[Custelcean, R., Moyer, B. A. & Hay, B. P. (2005). Chem. Commun. pp. 5971-5973.]). For related structures, see: Wu et al. (2008[Wu, B., Liang, J., Yang, J., Jia, C., Yang, X. J., Zhang, H., Tang, N. & Janiak, C. (2008). Chem. Commun. pp. 1762-1764.]); Saeed et al. (2010[Saeed, M. A., Fronczek, F. R. & Hossain, M. A. (2010). Acta Cryst. E66, o656-o657.]).

[Scheme 1]

Experimental

Crystal data

  • C33H26N6O2

  • Mr = 538.60

  • Tetragonal, P 43

  • a = 18.1345 (6) Å

  • c = 17.1405 (11) Å

  • V = 5636.8 (5) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 100 K

  • 0.35 × 0.34 × 0.34 mm
Data collection

  • Bruker APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2001[Sheldrick, G. M. (2001). SADABS. University of Göttingen, Germany.]) Tmin = 0.972, Tmax = 0.973

  • 65350 measured reflections

  • 5737 independent reflections

  • 4589 reflections with I > 2σ(I)

  • Rint = 0.104
Refinement

  • R[F2 > 2σ(F2)] = 0.046

  • wR(F2) = 0.104

  • S = 1.00

  • 5737 reflections

  • 767 parameters

  • 1 restraint

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

  • Δρmax = 0.16 e Å−3

  • Δρmin = −0.17 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N11A—H11A⋯N1A 0.74 (4) 2.27 (4) 2.625 (4) 110 (3)
N11A—H11A⋯O13Ai 0.74 (4) 2.41 (4) 3.101 (3) 155 (4)
N14A—H14A⋯O13Ai 0.86 (4) 1.97 (4) 2.810 (4) 166 (3)
N28A—H28A⋯O30Aii 0.78 (4) 2.05 (4) 2.827 (4) 170 (4)
N31A—H31A⋯O30Aii 0.88 (4) 2.56 (4) 3.293 (4) 141 (3)
N31A—H31A⋯N39A 0.88 (4) 2.14 (4) 2.635 (4) 114 (3)
N11B—H11B⋯N1B 0.90 (4) 2.13 (4) 2.645 (4) 116 (3)
N11B—H11B⋯O30Biii 0.90 (4) 2.46 (4) 3.172 (4) 136 (3)
N14B—H14B⋯O30Biii 0.80 (3) 1.98 (4) 2.772 (4) 167 (3)
N28B—H28B⋯O13Biv 0.87 (4) 1.94 (4) 2.786 (4) 161 (4)
N31B—H31B⋯O13Biv 0.90 (4) 2.36 (3) 3.115 (4) 141 (3)
N31B—H31B⋯N39B 0.90 (4) 2.14 (3) 2.647 (4) 115 (3)
Symmetry codes: (i) [y, -x+1, z+{\script{1\over 4}}]; (ii) [y+1, -x+1, z+{\script{1\over 4}}]; (iii) [-y+1, x-1, z-{\script{1\over 4}}]; (iv) [-y+1, x, z-{\script{1\over 4}}].

Data collection: SMART (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SMART and SAINT. 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811053220/rk2320sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811053220/rk2320Isup2.hkl

checkCIF report


Comment top

In supramolecular chemistry, urea-based compounds are known to effectively bind anions in which a urea group acts as H-bond donors. For examples, acyclic urea hosts containing one or two binding sites were able to form complexes with phosphonates, sulfates and carboxylates in CHCl3 (Smith et al., 1992) or acetate and glutarate in DMSO (Fan et al., 1993). Tren-based urea receptors with three urea units were recently reported showing high affinity and selectivity for various inorganic anions (Custelcean et al., 2005; Wu et al., 2008; Caltagirone et al., 2008). In an earlier paper, we reported a seven-coordinated hydrogen sulfate formed with three tren-based ureas via six NH···O bonds (dN···O = 2.85-3.09Å) and one OH···O bond (dO···O = 2.57Å) (Pramanik et al., 2011). In an effort to design selective receptors with a rigid framework, we synthesized a dipodal receptor consisting of a diphenylmethane linked with two quinoline groups. The title bis-urea compound contains two urea binding sites that could be an effective receptor for binding of variety of anions.

The bis-urea receptor crystallized in the tetragonal space group P43 with two molecules (Fig. 1) in the asymmetric unit. The asymmetric unit contains two molecules - A and B. As shown in Fig. 1, the two carbonyls of the two urea fragments of each molecule are oriented in the same direction. Two phenyl rings are twisted giving dihedral angles of 81.36 (8)° for A and 87.20 (9)° for B. Each pyridine nitrogen of the quinoline groups is involved in strong intramolecular hydrogen bonding with one NH group with N···N distances ranging from 2.625 (4)Å to 2.647 (4)Å. Each quinoline plane is nearly parallel with the attached urea group. There was no intermolecular hydrogen bonding between the two molecules. Each oxygen atom is bonded with two intermolecular NH···O hydrogen bonds with N···O distances ranging from 2.772 (4)Å to 3.293 (4)Å. Similar H-bonding interactions were observed in a related bis urea receptor (Saeed et al., 2010). In the extended structure viewed along the c axis, quinoline planes are found to be antiparallel (Fig. 2). No π···π stacking was observed between the aromatic groups.

Related literature top

For general background to urea-based compounds in supramolecular chemistry, see: Fan et al. (1993); Smith et al. (1992); Pramanik et al. (2011); Caltagirone et al. (2008); Custelcean et al. (2005). For related structures, see: Wu et al. (2008); Saeed et al. (2010).

Experimental top

Synthesis of 1: 4,4'-methylenebis(phenylisocyanate) (500 mg, 1.99 mmol) was reacted with 8-aminoquinoline (576 mg, 3.99 mmol) in dichloromethane (500 ml) at room temperature under constant stirring. The mixture was refluxed for 5 h. A white precipitate was formed which collected by filtration. The precipitate washed by dichloromethane in several times and dried under vacuum to give a white solid (1.022 g, 95% yield). δH (500 MHz; DMSO-d6) 9.80 (2H, s, Ar–NH), 9.66 (2H, s, Ar–NH), 8.91 (2H, d, J = 4.15 Hz, ArH), 8.54 (2H, dd, J1 = 3.1 Hz, J2 = 3.25 Hz, J3 = 3.55 Hz, ArH), 8.38 (2H, d, J = 8.25 Hz, ArH), 7.62 (2H, dd, J1 = 4.15 Hz, J2 = 3.95 Hz, J3 = 4.2 Hz, ArH) 7.55 (2H, d, J = 2 Hz, ArH), 7.54 (2H, d, J = 0.55 Hz, ArH), 7.41 (4H, d, J = 7.6 Hz, ArH), 7.15 (2H, d, J = 5.75 Hz, ArH) 3.84 (4H, s, αH). δC (125 MHz; DMSO-d6) δ 152.4 (CO), 148.3 (CAr), 137.744 (CHAr), 137.7 (CHAr), 136.616 (CHAr), 135.9 (CHAr), 135.1 (CHAr), 129.0 (CHAr), 127.907 (CHAr), 127.2 (CHAr), 122.018 (CHAr), 119.7 (CHAr), 118.3 (CHAr), 114.3 (CHAr). ESI-MS(+ve): m/z 539.2 (MH+).

Refinement top

H atoms bonded to carbons were positioned geometrically and refined using a riding model with C–H = 0.99Å, Uiso(H) = 1.2Ueq(C). H atoms bonded to N atoms were located on a difference map and their positions were refined independently with Uiso(H) = 1.2Ueq(N).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound showing two molecules (A and B) with the atom-numbering scheme. The hydrogen atoms have been omitted clarity. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. Packing structure of title compound viewed along c axis.
3,3'-Bis(quinolin-8-yl)-1,1'-[4,4'-methylenebis(4,1-phenylene)]diurea top
Crystal data top
C33H26N6O2Dx = 1.269 Mg m−3
Mr = 538.60Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P43Cell parameters from 5315 reflections
Hall symbol: P 4cwθ = 2.3–25.6°
a = 18.1345 (6) ŵ = 0.08 mm−1
c = 17.1405 (11) ÅT = 100 K
V = 5636.8 (5) Å3Prism, colourless
Z = 80.35 × 0.34 × 0.34 mm
F(000) = 2256
Data collection top
Bruker APEX CCD
diffractometer		5737 independent reflections
Radiation source: fine-focus sealed tube4589 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.104
ϕ and ω scansθmax = 26.0°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)		h = −21→22
Tmin = 0.972, Tmax = 0.973k = −22→22
65350 measured reflectionsl = −21→21
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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.056P)2 + 0.2P]
where P = (Fo2 + 2Fc2)/3
5737 reflections(Δ/σ)max = 0.009
767 parametersΔρmax = 0.16 e Å−3
1 restraintΔρmin = −0.17 e Å−3
Crystal data top
C33H26N6O2Z = 8
Mr = 538.60Mo Kα radiation
Tetragonal, P43µ = 0.08 mm−1
a = 18.1345 (6) ÅT = 100 K
c = 17.1405 (11) Å0.35 × 0.34 × 0.34 mm
V = 5636.8 (5) Å3
Data collection top
Bruker APEX CCD
diffractometer		5737 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)		4589 reflections with I > 2σ(I)
Tmin = 0.972, Tmax = 0.973Rint = 0.104
65350 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0461 restraint
wR(F2) = 0.104H atoms treated by a mixture of independent and constrained refinement
S = 1.00Δρmax = 0.16 e Å−3
5737 reflectionsΔρmin = −0.17 e Å−3
767 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N1A0.46023 (16)0.60598 (15)1.03005 (16)0.0295 (7)
C2A0.4337 (2)0.6382 (2)1.0937 (2)0.0376 (9)
H2A0.43860.61301.14200.045*
C3A0.3988 (2)0.7074 (2)1.0939 (2)0.0417 (10)
H3A0.38120.72821.14120.050*
C4A0.3906 (2)0.7445 (2)1.0250 (2)0.0403 (10)
H4A0.36640.79101.02390.048*
C5A0.4152 (2)0.7487 (2)0.8829 (2)0.0397 (10)
H5A0.39110.79500.87810.048*
C6A0.4468 (2)0.7169 (2)0.8194 (2)0.0397 (9)
H6A0.44490.74180.77070.048*
C7A0.4820 (2)0.6482 (2)0.8240 (2)0.0344 (9)
H7A0.50340.62700.77860.041*
C8A0.48556 (18)0.61166 (18)0.89402 (19)0.0262 (8)
C9A0.45352 (19)0.64369 (19)0.96179 (19)0.0281 (8)
C10A0.41827 (19)0.71349 (19)0.9554 (2)0.0327 (9)
N11A0.51799 (16)0.54288 (16)0.90650 (15)0.0250 (7)
H11A0.510 (2)0.5245 (19)0.944 (2)0.030*
C12A0.55774 (18)0.50051 (18)0.85636 (18)0.0238 (7)
O13A0.57356 (12)0.51987 (13)0.78897 (12)0.0271 (5)
N14A0.57950 (16)0.43545 (16)0.88795 (16)0.0265 (7)
H14A0.5608 (19)0.4245 (19)0.932 (2)0.032*
C15A0.61679 (17)0.37771 (18)0.85041 (18)0.0223 (7)
C16A0.60452 (18)0.30632 (18)0.87673 (19)0.0262 (8)
H16A0.57190.29830.91930.031*
C17A0.63877 (19)0.24690 (19)0.84222 (19)0.0291 (8)
H17A0.62870.19850.86070.035*
C18A0.68806 (18)0.25667 (18)0.78052 (18)0.0259 (8)
C19A0.70224 (19)0.32855 (19)0.75691 (19)0.0295 (8)
H19A0.73660.33660.71590.035*
C20A0.66824 (18)0.38898 (19)0.79072 (18)0.0264 (8)
H20A0.67970.43750.77360.032*
C21A0.7215 (2)0.19087 (19)0.7397 (2)0.0322 (8)
H21A0.75090.20850.69480.039*
H21B0.68130.15970.71900.039*
C22A0.77037 (18)0.14410 (19)0.79122 (18)0.0258 (8)
C23A0.77950 (19)0.07013 (19)0.77598 (19)0.0312 (8)
H23A0.75240.04850.73440.037*
C24A0.82653 (19)0.02622 (19)0.81896 (19)0.0312 (8)
H24A0.8308−0.02490.80760.037*
C25A0.86764 (19)0.05729 (19)0.87904 (19)0.0299 (8)
C26A0.8583 (2)0.1311 (2)0.8964 (2)0.0347 (9)
H26A0.88520.15260.93810.042*
C27A0.8099 (2)0.1739 (2)0.8534 (2)0.0335 (9)
H27A0.80350.22440.86650.040*
N28A0.91573 (19)0.01542 (18)0.92631 (17)0.0349 (8)
H28A0.916 (2)0.028 (2)0.970 (2)0.042*
C29A0.95213 (19)−0.0459 (2)0.9045 (2)0.0312 (8)
O30A0.95297 (14)−0.06992 (14)0.83709 (13)0.0365 (6)
N31A0.98804 (16)−0.08013 (17)0.96440 (17)0.0306 (7)
H31A0.988 (2)−0.060 (2)1.011 (2)0.037*
C32A1.02455 (18)−0.14765 (19)0.9634 (2)0.0263 (8)
C33A1.03786 (19)−0.1903 (2)0.8987 (2)0.0319 (8)
H33A1.0230−0.17330.84860.038*
C34A1.0736 (2)−0.2591 (2)0.9060 (2)0.0354 (9)
H34A1.0824−0.28800.86070.042*
C35A1.0956 (2)−0.2849 (2)0.9770 (2)0.0366 (9)
H35A1.1195−0.33130.98080.044*
C36A1.1021 (2)−0.2668 (2)1.1212 (2)0.0392 (10)
H36A1.1251−0.31331.12880.047*
C37A1.0870 (2)−0.2225 (2)1.1831 (2)0.0400 (10)
H37A1.0994−0.23791.23440.048*
C38A1.0530 (2)−0.1537 (2)1.1706 (2)0.0381 (9)
H38A1.0432−0.12361.21470.046*
N39A1.03389 (16)−0.12856 (17)1.10094 (17)0.0329 (7)
C40A1.04785 (18)−0.17355 (18)1.0386 (2)0.0274 (8)
C41A1.08295 (19)−0.2426 (2)1.0450 (2)0.0332 (9)
N1B0.37326 (16)−0.06095 (15)0.81946 (16)0.0295 (7)
C2B0.3446 (2)−0.08341 (19)0.7527 (2)0.0340 (9)
H2B0.3718−0.07530.70620.041*
C3B0.2751 (2)−0.1190 (2)0.7470 (2)0.0370 (9)
H3B0.2568−0.13400.69750.044*
C4B0.2352 (2)−0.1314 (2)0.8121 (2)0.0348 (9)
H4B0.1888−0.15540.80880.042*
C5B0.2250 (2)−0.1194 (2)0.9571 (2)0.0331 (8)
H5B0.1788−0.14400.95780.040*
C6B0.2555 (2)−0.09456 (19)1.0241 (2)0.0344 (9)
H6B0.2296−0.10191.07170.041*
C7B0.32440 (19)−0.05801 (18)1.0262 (2)0.0285 (8)
H7B0.3444−0.04161.07440.034*
C8B0.36206 (19)−0.04658 (18)0.95747 (19)0.0256 (8)
C9B0.33188 (19)−0.07224 (18)0.88527 (19)0.0266 (8)
C10B0.26309 (19)−0.10829 (18)0.8857 (2)0.0290 (8)
N11B0.43079 (16)−0.01080 (16)0.95094 (17)0.0285 (7)
H11B0.448 (2)−0.014 (2)0.902 (2)0.039 (11)*
C12B0.4623 (2)0.03466 (18)1.00490 (19)0.0273 (8)
O13B0.43275 (13)0.05017 (13)1.06738 (13)0.0313 (6)
N14B0.52838 (17)0.06201 (16)0.98239 (18)0.0292 (7)
H14B0.5448 (18)0.0504 (18)0.941 (2)0.019 (9)*
C15B0.56730 (19)0.11839 (18)1.02099 (19)0.0253 (7)
C16B0.6440 (2)0.11995 (19)1.01518 (19)0.0303 (8)
H16B0.66920.08240.98730.036*
C17B0.6831 (2)0.17647 (19)1.0502 (2)0.0310 (8)
H17B0.73540.17691.04620.037*
C18B0.64819 (18)0.23261 (19)1.09119 (19)0.0271 (8)
C19B0.57124 (19)0.23141 (19)1.09414 (19)0.0281 (8)
H19B0.54590.26971.12090.034*
C20B0.53112 (19)0.17585 (18)1.05906 (18)0.0283 (8)
H20B0.47880.17681.06090.034*
C21B0.69101 (19)0.2921 (2)1.1334 (2)0.0327 (9)
H21C0.70510.27331.18550.039*
H21D0.65830.33511.14130.039*
C22B0.76001 (19)0.31761 (19)1.0915 (2)0.0302 (8)
C23B0.7541 (2)0.3536 (2)1.0195 (2)0.0376 (9)
H23B0.70720.35900.99560.045*
C24B0.8160 (2)0.3813 (2)0.9832 (2)0.0360 (9)
H24B0.81130.40530.93420.043*
C25B0.88455 (19)0.37463 (19)1.01684 (19)0.0304 (8)
C26B0.8918 (2)0.3362 (2)1.08675 (19)0.0321 (8)
H26B0.93900.32921.10970.038*
C27B0.8290 (2)0.30840 (19)1.1222 (2)0.0318 (8)
H27B0.83410.28191.16970.038*
N28B0.94570 (17)0.40586 (18)0.97736 (18)0.0346 (8)
H28B0.937 (2)0.417 (2)0.929 (2)0.049 (12)*
C29B1.0048 (2)0.4385 (2)1.0114 (2)0.0307 (8)
O30B1.01626 (14)0.43771 (14)1.08229 (13)0.0360 (6)
N31B1.05041 (16)0.47147 (16)0.95887 (17)0.0284 (7)
H31B1.0378 (17)0.4754 (17)0.908 (2)0.025 (9)*
C32B1.11753 (19)0.50756 (18)0.9727 (2)0.0278 (8)
C33B1.1492 (2)0.5185 (2)1.0449 (2)0.0340 (9)
H33B1.12480.50191.09060.041*
C34B1.2180 (2)0.55449 (19)1.0508 (2)0.0353 (9)
H34B1.23920.56191.10090.042*
C35B1.2549 (2)0.5788 (2)0.9863 (2)0.0376 (9)
H35B1.30130.60250.99170.045*
C36B1.2583 (2)0.5916 (2)0.8421 (2)0.0390 (9)
H36B1.30480.61560.84380.047*
C37B1.2245 (2)0.5790 (2)0.7724 (2)0.0401 (10)
H37B1.24770.59320.72510.048*
C38B1.1550 (2)0.5447 (2)0.7709 (2)0.0371 (9)
H38B1.13170.53760.72180.045*
N39B1.12023 (16)0.52202 (16)0.83423 (16)0.0307 (7)
C40B1.15499 (19)0.53350 (19)0.9046 (2)0.0290 (8)
C41B1.22385 (19)0.56873 (19)0.9114 (2)0.0316 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N1A0.0325 (16)0.0316 (16)0.0246 (15)−0.0034 (13)0.0030 (13)−0.0037 (14)
C2A0.041 (2)0.040 (2)0.032 (2)−0.0048 (18)0.0110 (18)−0.0078 (18)
C3A0.043 (2)0.038 (2)0.045 (2)0.0004 (19)0.018 (2)−0.015 (2)
C4A0.041 (2)0.031 (2)0.048 (2)0.0005 (18)0.017 (2)−0.0058 (19)
C5A0.043 (2)0.028 (2)0.049 (2)0.0086 (17)0.001 (2)0.0047 (19)
C6A0.052 (2)0.034 (2)0.034 (2)0.0082 (19)−0.0014 (19)0.0050 (18)
C7A0.046 (2)0.034 (2)0.0234 (19)0.0063 (18)0.0017 (17)0.0002 (16)
C8A0.0278 (19)0.0247 (19)0.0262 (18)0.0015 (15)−0.0031 (15)0.0007 (15)
C9A0.0279 (19)0.0293 (19)0.0271 (19)−0.0001 (15)0.0036 (15)0.0002 (16)
C10A0.028 (2)0.027 (2)0.043 (2)−0.0002 (16)0.0069 (17)−0.0069 (17)
N11A0.0351 (17)0.0285 (17)0.0115 (13)0.0057 (13)0.0046 (13)0.0051 (12)
C12A0.0290 (19)0.0261 (18)0.0163 (17)0.0017 (15)−0.0036 (15)0.0017 (15)
O13A0.0327 (13)0.0356 (14)0.0131 (12)0.0034 (11)0.0010 (10)0.0031 (10)
N14A0.0326 (17)0.0314 (17)0.0155 (14)0.0059 (13)0.0066 (13)0.0029 (13)
C15A0.0224 (17)0.0299 (19)0.0146 (16)0.0017 (14)0.0003 (14)−0.0007 (14)
C16A0.0267 (19)0.032 (2)0.0195 (16)0.0009 (16)−0.0003 (14)0.0062 (15)
C17A0.0329 (19)0.0282 (19)0.0261 (18)0.0031 (15)−0.0022 (16)0.0049 (16)
C18A0.0286 (19)0.0288 (19)0.0203 (17)0.0049 (15)−0.0069 (15)−0.0006 (15)
C19A0.032 (2)0.037 (2)0.0202 (17)0.0007 (16)0.0033 (15)−0.0025 (16)
C20A0.0299 (18)0.0287 (19)0.0205 (17)0.0011 (15)0.0024 (15)−0.0008 (15)
C21A0.039 (2)0.035 (2)0.0230 (18)0.0078 (17)−0.0076 (16)−0.0064 (16)
C22A0.0297 (19)0.0309 (19)0.0169 (16)0.0065 (15)−0.0008 (15)0.0012 (15)
C23A0.035 (2)0.035 (2)0.0240 (18)0.0012 (17)−0.0029 (16)−0.0060 (16)
C24A0.042 (2)0.028 (2)0.0237 (18)0.0075 (17)−0.0012 (17)−0.0025 (15)
C25A0.037 (2)0.033 (2)0.0201 (17)0.0117 (17)0.0028 (16)0.0021 (15)
C26A0.041 (2)0.036 (2)0.0270 (19)0.0038 (18)−0.0078 (17)−0.0045 (17)
C27A0.042 (2)0.029 (2)0.030 (2)0.0064 (17)−0.0067 (17)−0.0046 (16)
N28A0.050 (2)0.040 (2)0.0151 (15)0.0179 (16)−0.0053 (14)−0.0041 (14)
C29A0.034 (2)0.039 (2)0.0200 (18)0.0092 (17)0.0023 (16)−0.0011 (16)
O30A0.0459 (15)0.0472 (16)0.0165 (12)0.0181 (13)−0.0013 (11)−0.0019 (12)
N31A0.0374 (18)0.0373 (18)0.0171 (14)0.0103 (14)−0.0002 (13)−0.0008 (14)
C32A0.0232 (18)0.0278 (19)0.0280 (19)0.0033 (15)0.0000 (15)0.0008 (16)
C33A0.032 (2)0.037 (2)0.0272 (19)0.0034 (16)0.0045 (16)0.0049 (17)
C34A0.037 (2)0.033 (2)0.036 (2)0.0060 (17)0.0016 (18)−0.0041 (17)
C35A0.033 (2)0.0250 (19)0.051 (2)0.0009 (16)−0.0020 (19)0.0051 (18)
C36A0.034 (2)0.036 (2)0.047 (2)−0.0016 (17)−0.0064 (19)0.0160 (19)
C37A0.038 (2)0.051 (3)0.031 (2)−0.0075 (19)−0.0114 (17)0.0152 (19)
C38A0.039 (2)0.047 (2)0.029 (2)−0.0064 (19)−0.0054 (17)0.0054 (18)
N39A0.0308 (17)0.0439 (19)0.0240 (15)−0.0008 (14)−0.0057 (13)0.0035 (14)
C40A0.0236 (18)0.0294 (19)0.0292 (19)−0.0009 (15)0.0019 (15)0.0048 (16)
C41A0.0257 (19)0.039 (2)0.034 (2)−0.0048 (17)−0.0017 (16)0.0053 (18)
N1B0.0409 (18)0.0243 (16)0.0234 (15)0.0026 (13)−0.0019 (14)−0.0022 (12)
C2B0.044 (2)0.033 (2)0.0245 (19)0.0024 (18)−0.0009 (17)−0.0058 (16)
C3B0.046 (2)0.033 (2)0.032 (2)0.0064 (18)−0.0122 (18)−0.0096 (17)
C4B0.032 (2)0.033 (2)0.039 (2)0.0014 (17)−0.0070 (18)−0.0085 (17)
C5B0.031 (2)0.031 (2)0.037 (2)−0.0030 (16)0.0010 (17)−0.0002 (17)
C6B0.036 (2)0.033 (2)0.035 (2)−0.0004 (17)0.0032 (17)0.0076 (17)
C7B0.035 (2)0.0271 (18)0.0232 (18)−0.0023 (16)0.0004 (16)0.0013 (15)
C8B0.030 (2)0.0234 (18)0.0233 (18)0.0036 (15)−0.0004 (15)0.0024 (14)
C9B0.0298 (19)0.0250 (18)0.0251 (18)0.0041 (15)−0.0007 (15)−0.0011 (15)
C10B0.031 (2)0.0221 (18)0.034 (2)0.0035 (15)−0.0048 (16)−0.0022 (15)
N11B0.0359 (18)0.0329 (17)0.0167 (15)−0.0084 (14)0.0028 (13)0.0003 (13)
C12B0.038 (2)0.0216 (18)0.0226 (19)−0.0039 (16)−0.0006 (16)0.0016 (15)
O13B0.0428 (15)0.0319 (13)0.0191 (12)−0.0068 (11)0.0066 (11)−0.0041 (10)
N14B0.0385 (19)0.0328 (17)0.0162 (15)−0.0068 (14)0.0066 (14)−0.0058 (13)
C15B0.0316 (19)0.0269 (18)0.0174 (16)−0.0026 (15)0.0013 (15)0.0008 (14)
C16B0.037 (2)0.031 (2)0.0229 (18)0.0009 (17)0.0052 (16)−0.0016 (16)
C17B0.0274 (19)0.037 (2)0.0285 (19)−0.0028 (16)0.0025 (16)0.0019 (17)
C18B0.0298 (19)0.034 (2)0.0175 (16)−0.0073 (16)0.0027 (15)0.0021 (15)
C19B0.035 (2)0.0302 (19)0.0188 (16)−0.0015 (16)0.0037 (15)−0.0016 (15)
C20B0.032 (2)0.0323 (19)0.0209 (17)−0.0013 (16)0.0023 (15)0.0008 (15)
C21B0.033 (2)0.036 (2)0.029 (2)−0.0087 (17)0.0023 (16)−0.0052 (16)
C22B0.035 (2)0.031 (2)0.0252 (18)−0.0074 (16)0.0019 (16)0.0014 (16)
C23B0.037 (2)0.044 (2)0.032 (2)−0.0118 (18)−0.0086 (17)0.0049 (18)
C24B0.042 (2)0.045 (2)0.0207 (18)−0.0118 (19)−0.0072 (17)0.0090 (17)
C25B0.035 (2)0.036 (2)0.0205 (18)−0.0094 (17)−0.0004 (16)0.0003 (16)
C26B0.030 (2)0.042 (2)0.0243 (18)−0.0020 (17)−0.0005 (16)0.0026 (17)
C27B0.038 (2)0.035 (2)0.0224 (18)−0.0053 (17)−0.0021 (16)0.0062 (16)
N28B0.0391 (19)0.051 (2)0.0137 (15)−0.0162 (16)−0.0035 (14)0.0038 (14)
C29B0.036 (2)0.033 (2)0.0234 (19)−0.0075 (17)0.0023 (16)0.0029 (16)
O30B0.0433 (16)0.0460 (16)0.0188 (13)−0.0135 (12)−0.0044 (11)−0.0021 (11)
N31B0.0299 (17)0.0401 (18)0.0151 (15)−0.0067 (14)−0.0007 (13)−0.0021 (13)
C32B0.0290 (19)0.0247 (18)0.0297 (19)−0.0019 (15)0.0008 (16)0.0005 (15)
C33B0.033 (2)0.035 (2)0.033 (2)0.0024 (17)−0.0025 (17)0.0012 (17)
C34B0.035 (2)0.034 (2)0.038 (2)−0.0064 (17)−0.0080 (18)−0.0004 (18)
C35B0.028 (2)0.029 (2)0.056 (3)−0.0021 (16)−0.0111 (19)−0.0011 (19)
C36B0.028 (2)0.033 (2)0.055 (3)−0.0051 (17)0.0055 (19)0.007 (2)
C37B0.037 (2)0.043 (2)0.040 (2)−0.0006 (18)0.0123 (19)0.0117 (19)
C38B0.036 (2)0.040 (2)0.036 (2)0.0006 (18)0.0074 (18)0.0077 (18)
N39B0.0344 (17)0.0320 (17)0.0257 (16)−0.0013 (13)0.0058 (14)0.0023 (13)
C40B0.029 (2)0.0231 (19)0.035 (2)0.0047 (15)0.0012 (17)−0.0010 (16)
C41B0.0273 (19)0.026 (2)0.041 (2)0.0015 (16)0.0006 (17)0.0029 (17)
Geometric parameters (Å, º) top
N1A—C2A1.327 (4)N1B—C2B1.321 (4)
N1A—C9A1.361 (4)N1B—C9B1.370 (4)
C2A—C3A1.406 (5)C2B—C3B1.418 (5)
C2A—H2A0.9500C2B—H2B0.9500
C3A—C4A1.367 (6)C3B—C4B1.350 (5)
C3A—H3A0.9500C3B—H3B0.9500
C4A—C10A1.411 (5)C4B—C10B1.421 (5)
C4A—H4A0.9500C4B—H4B0.9500
C5A—C6A1.359 (5)C5B—C6B1.352 (5)
C5A—C10A1.398 (5)C5B—C10B1.420 (5)
C5A—H5A0.9500C5B—H5B0.9500
C6A—C7A1.401 (5)C6B—C7B1.415 (5)
C6A—H6A0.9500C6B—H6B0.9500
C7A—C8A1.373 (5)C7B—C8B1.378 (5)
C7A—H7A0.9500C7B—H7B0.9500
C8A—N11A1.396 (4)C8B—N11B1.410 (4)
C8A—C9A1.423 (5)C8B—C9B1.431 (5)
C9A—C10A1.422 (5)C9B—C10B1.408 (5)
N11A—C12A1.360 (4)N11B—C12B1.364 (4)
N11A—H11A0.74 (4)N11B—H11B0.90 (4)
C12A—O13A1.241 (4)C12B—O13B1.230 (4)
C12A—N14A1.357 (4)C12B—N14B1.353 (4)
N14A—C15A1.403 (4)N14B—C15B1.407 (4)
N14A—H14A0.86 (4)N14B—H14B0.80 (3)
C15A—C16A1.389 (4)C15B—C20B1.394 (5)
C15A—C20A1.400 (4)C15B—C16B1.394 (5)
C16A—C17A1.377 (5)C16B—C17B1.384 (5)
C16A—H16A0.9500C16B—H16B0.9500
C17A—C18A1.396 (5)C17B—C18B1.390 (5)
C17A—H17A0.9500C17B—H17B0.9500
C18A—C19A1.389 (5)C18B—C19B1.396 (5)
C18A—C21A1.511 (5)C18B—C21B1.513 (5)
C19A—C20A1.385 (5)C19B—C20B1.381 (5)
C19A—H19A0.9500C19B—H19B0.9500
C20A—H20A0.9500C20B—H20B0.9500
C21A—C22A1.511 (4)C21B—C22B1.515 (5)
C21A—H21A0.9900C21B—H21C0.9900
C21A—H21B0.9900C21B—H21D0.9900
C22A—C23A1.377 (5)C22B—C27B1.368 (5)
C22A—C27A1.393 (5)C22B—C23B1.400 (5)
C23A—C24A1.380 (5)C23B—C24B1.378 (5)
C23A—H23A0.9500C23B—H23B0.9500
C24A—C25A1.391 (5)C24B—C25B1.375 (5)
C24A—H24A0.9500C24B—H24B0.9500
C25A—C26A1.381 (5)C25B—C26B1.392 (5)
C25A—N28A1.412 (4)C25B—N28B1.417 (4)
C26A—C27A1.384 (5)C26B—C27B1.386 (5)
C26A—H26A0.9500C26B—H26B0.9500
C27A—H27A0.9500C27B—H27B0.9500
N28A—C29A1.346 (4)N28B—C29B1.355 (5)
N28A—H28A0.78 (4)N28B—H28B0.87 (4)
C29A—O30A1.234 (4)C29B—O30B1.234 (4)
C29A—N31A1.366 (4)C29B—N31B1.361 (4)
N31A—C32A1.392 (4)N31B—C32B1.402 (4)
N31A—H31A0.88 (4)N31B—H31B0.90 (4)
C32A—C33A1.374 (5)C32B—C33B1.379 (5)
C32A—C40A1.435 (5)C32B—C40B1.430 (5)
C33A—C34A1.413 (5)C33B—C34B1.412 (5)
C33A—H33A0.9500C33B—H33B0.9500
C34A—C35A1.363 (5)C34B—C35B1.365 (5)
C34A—H34A0.9500C34B—H34B0.9500
C35A—C41A1.414 (5)C35B—C41B1.413 (5)
C35A—H35A0.9500C35B—H35B0.9500
C36A—C37A1.357 (5)C36B—C37B1.362 (6)
C36A—C41A1.421 (5)C36B—C41B1.405 (5)
C36A—H36A0.9500C36B—H36B0.9500
C37A—C38A1.409 (5)C37B—C38B1.405 (5)
C37A—H37A0.9500C37B—H37B0.9500
C38A—N39A1.324 (4)C38B—N39B1.321 (4)
C38A—H38A0.9500C38B—H38B0.9500
N39A—C40A1.368 (4)N39B—C40B1.376 (4)
C40A—C41A1.409 (5)C40B—C41B1.408 (5)
C2A—N1A—C9A116.9 (3)C2B—N1B—C9B116.8 (3)
N1A—C2A—C3A123.9 (4)N1B—C2B—C3B123.4 (3)
N1A—C2A—H2A118.0N1B—C2B—H2B118.3
C3A—C2A—H2A118.0C3B—C2B—H2B118.3
C4A—C3A—C2A119.1 (3)C4B—C3B—C2B119.6 (3)
C4A—C3A—H3A120.4C4B—C3B—H3B120.2
C2A—C3A—H3A120.4C2B—C3B—H3B120.2
C3A—C4A—C10A119.7 (3)C3B—C4B—C10B119.6 (3)
C3A—C4A—H4A120.2C3B—C4B—H4B120.2
C10A—C4A—H4A120.2C10B—C4B—H4B120.2
C6A—C5A—C10A120.1 (3)C6B—C5B—C10B119.1 (3)
C6A—C5A—H5A120.0C6B—C5B—H5B120.5
C10A—C5A—H5A120.0C10B—C5B—H5B120.5
C5A—C6A—C7A121.7 (4)C5B—C6B—C7B122.6 (3)
C5A—C6A—H6A119.2C5B—C6B—H6B118.7
C7A—C6A—H6A119.2C7B—C6B—H6B118.7
C8A—C7A—C6A119.9 (3)C8B—C7B—C6B119.1 (3)
C8A—C7A—H7A120.0C8B—C7B—H7B120.4
C6A—C7A—H7A120.0C6B—C7B—H7B120.4
C7A—C8A—N11A125.8 (3)C7B—C8B—N11B125.1 (3)
C7A—C8A—C9A119.8 (3)C7B—C8B—C9B120.1 (3)
N11A—C8A—C9A114.3 (3)N11B—C8B—C9B114.8 (3)
N1A—C9A—C10A123.6 (3)N1B—C9B—C10B124.0 (3)
N1A—C9A—C8A117.4 (3)N1B—C9B—C8B117.0 (3)
C10A—C9A—C8A118.9 (3)C10B—C9B—C8B119.0 (3)
C5A—C10A—C4A123.7 (3)C9B—C10B—C5B120.1 (3)
C5A—C10A—C9A119.5 (3)C9B—C10B—C4B116.6 (3)
C4A—C10A—C9A116.7 (3)C5B—C10B—C4B123.4 (3)
C12A—N11A—C8A129.2 (3)C12B—N11B—C8B126.5 (3)
C12A—N11A—H11A114 (3)C12B—N11B—H11B122 (2)
C8A—N11A—H11A117 (3)C8B—N11B—H11B110 (2)
O13A—C12A—N14A123.4 (3)O13B—C12B—N14B123.4 (3)
O13A—C12A—N11A123.4 (3)O13B—C12B—N11B123.1 (3)
N14A—C12A—N11A113.2 (3)N14B—C12B—N11B113.5 (3)
C12A—N14A—C15A127.3 (3)C12B—N14B—C15B125.2 (3)
C12A—N14A—H14A116 (2)C12B—N14B—H14B119 (2)
C15A—N14A—H14A115 (2)C15B—N14B—H14B115 (2)
C16A—C15A—C20A118.7 (3)C20B—C15B—C16B119.2 (3)
C16A—C15A—N14A118.0 (3)C20B—C15B—N14B121.8 (3)
C20A—C15A—N14A123.2 (3)C16B—C15B—N14B118.8 (3)
C17A—C16A—C15A121.2 (3)C17B—C16B—C15B119.7 (3)
C17A—C16A—H16A119.4C17B—C16B—H16B120.1
C15A—C16A—H16A119.4C15B—C16B—H16B120.1
C16A—C17A—C18A121.0 (3)C16B—C17B—C18B121.9 (3)
C16A—C17A—H17A119.5C16B—C17B—H17B119.1
C18A—C17A—H17A119.5C18B—C17B—H17B119.1
C19A—C18A—C17A117.3 (3)C17B—C18B—C19B117.6 (3)
C19A—C18A—C21A122.1 (3)C17B—C18B—C21B122.0 (3)
C17A—C18A—C21A120.5 (3)C19B—C18B—C21B120.4 (3)
C20A—C19A—C18A122.6 (3)C20B—C19B—C18B121.5 (3)
C20A—C19A—H19A118.7C20B—C19B—H19B119.3
C18A—C19A—H19A118.7C18B—C19B—H19B119.3
C19A—C20A—C15A119.2 (3)C19B—C20B—C15B120.1 (3)
C19A—C20A—H20A120.4C19B—C20B—H20B120.0
C15A—C20A—H20A120.4C15B—C20B—H20B120.0
C18A—C21A—C22A114.1 (3)C18B—C21B—C22B114.5 (3)
C18A—C21A—H21A108.7C18B—C21B—H21C108.6
C22A—C21A—H21A108.7C22B—C21B—H21C108.6
C18A—C21A—H21B108.7C18B—C21B—H21D108.6
C22A—C21A—H21B108.7C22B—C21B—H21D108.6
H21A—C21A—H21B107.6H21C—C21B—H21D107.6
C23A—C22A—C27A117.4 (3)C27B—C22B—C23B117.8 (3)
C23A—C22A—C21A120.4 (3)C27B—C22B—C21B122.4 (3)
C27A—C22A—C21A122.1 (3)C23B—C22B—C21B119.8 (3)
C22A—C23A—C24A122.4 (3)C24B—C23B—C22B120.4 (3)
C22A—C23A—H23A118.8C24B—C23B—H23B119.8
C24A—C23A—H23A118.8C22B—C23B—H23B119.8
C23A—C24A—C25A119.5 (3)C25B—C24B—C23B121.0 (3)
C23A—C24A—H24A120.2C25B—C24B—H24B119.5
C25A—C24A—H24A120.2C23B—C24B—H24B119.5
C26A—C25A—C24A119.1 (3)C24B—C25B—C26B119.3 (3)
C26A—C25A—N28A118.3 (3)C24B—C25B—N28B118.2 (3)
C24A—C25A—N28A122.6 (3)C26B—C25B—N28B122.5 (3)
C25A—C26A—C27A120.5 (3)C27B—C26B—C25B118.8 (3)
C25A—C26A—H26A119.8C27B—C26B—H26B120.6
C27A—C26A—H26A119.8C25B—C26B—H26B120.6
C26A—C27A—C22A121.1 (3)C22B—C27B—C26B122.6 (3)
C26A—C27A—H27A119.5C22B—C27B—H27B118.7
C22A—C27A—H27A119.5C26B—C27B—H27B118.7
C29A—N28A—C25A126.0 (3)C29B—N28B—C25B126.0 (3)
C29A—N28A—H28A120 (3)C29B—N28B—H28B118 (3)
C25A—N28A—H28A114 (3)C25B—N28B—H28B113 (3)
O30A—C29A—N28A123.9 (3)O30B—C29B—N28B123.5 (3)
O30A—C29A—N31A122.5 (3)O30B—C29B—N31B123.6 (3)
N28A—C29A—N31A113.6 (3)N28B—C29B—N31B112.9 (3)
C29A—N31A—C32A128.2 (3)C29B—N31B—C32B128.4 (3)
C29A—N31A—H31A120 (2)C29B—N31B—H31B121 (2)
C32A—N31A—H31A112 (2)C32B—N31B—H31B110 (2)
C33A—C32A—N31A126.0 (3)C33B—C32B—N31B125.5 (3)
C33A—C32A—C40A119.3 (3)C33B—C32B—C40B119.2 (3)
N31A—C32A—C40A114.7 (3)N31B—C32B—C40B115.3 (3)
C32A—C33A—C34A120.4 (3)C32B—C33B—C34B120.0 (3)
C32A—C33A—H33A119.8C32B—C33B—H33B120.0
C34A—C33A—H33A119.8C34B—C33B—H33B120.0
C35A—C34A—C33A121.1 (4)C35B—C34B—C33B121.6 (3)
C35A—C34A—H34A119.4C35B—C34B—H34B119.2
C33A—C34A—H34A119.4C33B—C34B—H34B119.2
C34A—C35A—C41A120.2 (3)C34B—C35B—C41B119.9 (3)
C34A—C35A—H35A119.9C34B—C35B—H35B120.0
C41A—C35A—H35A119.9C41B—C35B—H35B120.0
C37A—C36A—C41A119.1 (4)C37B—C36B—C41B119.5 (3)
C37A—C36A—H36A120.4C37B—C36B—H36B120.3
C41A—C36A—H36A120.5C41B—C36B—H36B120.3
C36A—C37A—C38A119.6 (3)C36B—C37B—C38B119.6 (4)
C36A—C37A—H37A120.2C36B—C37B—H37B120.2
C38A—C37A—H37A120.2C38B—C37B—H37B120.2
N39A—C38A—C37A123.8 (4)N39B—C38B—C37B123.4 (4)
N39A—C38A—H38A118.1N39B—C38B—H38B118.3
C37A—C38A—H38A118.1C37B—C38B—H38B118.3
C38A—N39A—C40A116.8 (3)C38B—N39B—C40B117.0 (3)
N39A—C40A—C41A123.5 (3)N39B—C40B—C41B123.2 (3)
N39A—C40A—C32A116.8 (3)N39B—C40B—C32B116.6 (3)
C41A—C40A—C32A119.6 (3)C41B—C40B—C32B120.2 (3)
C40A—C41A—C35A119.4 (3)C36B—C41B—C40B117.2 (3)
C40A—C41A—C36A117.1 (3)C36B—C41B—C35B123.6 (3)
C35A—C41A—C36A123.5 (3)C40B—C41B—C35B119.2 (3)
C9A—N1A—C2A—C3A0.9 (5)C9B—N1B—C2B—C3B−1.2 (5)
N1A—C2A—C3A—C4A0.5 (6)N1B—C2B—C3B—C4B−0.2 (5)
C2A—C3A—C4A—C10A−1.1 (6)C2B—C3B—C4B—C10B0.3 (5)
C10A—C5A—C6A—C7A0.9 (6)C10B—C5B—C6B—C7B−0.4 (5)
C5A—C6A—C7A—C8A−0.3 (6)C5B—C6B—C7B—C8B0.5 (5)
C6A—C7A—C8A—N11A179.1 (3)C6B—C7B—C8B—N11B179.7 (3)
C6A—C7A—C8A—C9A−0.1 (5)C6B—C7B—C8B—C9B−0.7 (5)
C2A—N1A—C9A—C10A−1.9 (5)C2B—N1B—C9B—C10B2.5 (5)
C2A—N1A—C9A—C8A176.4 (3)C2B—N1B—C9B—C8B−178.7 (3)
C7A—C8A—C9A—N1A−178.4 (3)C7B—C8B—C9B—N1B−178.1 (3)
N11A—C8A—C9A—N1A2.3 (4)N11B—C8B—C9B—N1B1.5 (4)
C7A—C8A—C9A—C10A0.0 (5)C7B—C8B—C9B—C10B0.8 (5)
N11A—C8A—C9A—C10A−179.4 (3)N11B—C8B—C9B—C10B−179.6 (3)
C6A—C5A—C10A—C4A176.4 (4)N1B—C9B—C10B—C5B178.2 (3)
C6A—C5A—C10A—C9A−1.0 (6)C8B—C9B—C10B—C5B−0.6 (5)
C3A—C4A—C10A—C5A−177.2 (4)N1B—C9B—C10B—C4B−2.3 (5)
C3A—C4A—C10A—C9A0.3 (5)C8B—C9B—C10B—C4B178.9 (3)
N1A—C9A—C10A—C5A178.8 (3)C6B—C5B—C10B—C9B0.5 (5)
C8A—C9A—C10A—C5A0.6 (5)C6B—C5B—C10B—C4B−179.0 (3)
N1A—C9A—C10A—C4A1.3 (5)C3B—C4B—C10B—C9B0.8 (5)
C8A—C9A—C10A—C4A−177.0 (3)C3B—C4B—C10B—C5B−179.6 (3)
C7A—C8A—N11A—C12A6.3 (6)C7B—C8B—N11B—C12B−18.5 (5)
C9A—C8A—N11A—C12A−174.5 (3)C9B—C8B—N11B—C12B161.9 (3)
C8A—N11A—C12A—O13A2.6 (6)C8B—N11B—C12B—O13B−0.4 (5)
C8A—N11A—C12A—N14A−178.5 (3)C8B—N11B—C12B—N14B−179.2 (3)
O13A—C12A—N14A—C15A−5.6 (5)O13B—C12B—N14B—C15B−9.0 (5)
N11A—C12A—N14A—C15A175.5 (3)N11B—C12B—N14B—C15B169.8 (3)
C12A—N14A—C15A—C16A−150.1 (3)C12B—N14B—C15B—C20B−33.3 (5)
C12A—N14A—C15A—C20A33.2 (5)C12B—N14B—C15B—C16B152.2 (3)
C20A—C15A—C16A—C17A−3.7 (5)C20B—C15B—C16B—C17B3.0 (5)
N14A—C15A—C16A—C17A179.5 (3)N14B—C15B—C16B—C17B177.6 (3)
C15A—C16A—C17A—C18A1.2 (5)C15B—C16B—C17B—C18B−0.3 (5)
C16A—C17A—C18A—C19A1.5 (5)C16B—C17B—C18B—C19B−1.8 (5)
C16A—C17A—C18A—C21A−176.0 (3)C16B—C17B—C18B—C21B176.5 (3)
C17A—C18A—C19A—C20A−1.7 (5)C17B—C18B—C19B—C20B1.2 (5)
C21A—C18A—C19A—C20A175.8 (3)C21B—C18B—C19B—C20B−177.1 (3)
C18A—C19A—C20A—C15A−0.8 (5)C18B—C19B—C20B—C15B1.4 (5)
C16A—C15A—C20A—C19A3.5 (5)C16B—C15B—C20B—C19B−3.5 (5)
N14A—C15A—C20A—C19A−179.9 (3)N14B—C15B—C20B—C19B−177.9 (3)
C19A—C18A—C21A—C22A118.7 (4)C17B—C18B—C21B—C22B37.5 (5)
C17A—C18A—C21A—C22A−63.9 (4)C19B—C18B—C21B—C22B−144.3 (3)
C18A—C21A—C22A—C23A152.7 (3)C18B—C21B—C22B—C27B−116.6 (4)
C18A—C21A—C22A—C27A−29.9 (5)C18B—C21B—C22B—C23B64.9 (4)
C27A—C22A—C23A—C24A−1.0 (5)C27B—C22B—C23B—C24B−2.7 (5)
C21A—C22A—C23A—C24A176.5 (3)C21B—C22B—C23B—C24B175.8 (3)
C22A—C23A—C24A—C25A−1.3 (5)C22B—C23B—C24B—C25B−0.4 (6)
C23A—C24A—C25A—C26A2.5 (5)C23B—C24B—C25B—C26B3.1 (6)
C23A—C24A—C25A—N28A178.8 (3)C23B—C24B—C25B—N28B−178.5 (3)
C24A—C25A—C26A—C27A−1.4 (5)C24B—C25B—C26B—C27B−2.7 (5)
N28A—C25A—C26A—C27A−177.8 (3)N28B—C25B—C26B—C27B179.0 (3)
C25A—C26A—C27A—C22A−0.9 (6)C23B—C22B—C27B—C26B3.1 (5)
C23A—C22A—C27A—C26A2.1 (5)C21B—C22B—C27B—C26B−175.4 (3)
C21A—C22A—C27A—C26A−175.4 (3)C25B—C26B—C27B—C22B−0.5 (5)
C26A—C25A—N28A—C29A−154.3 (4)C24B—C25B—N28B—C29B144.2 (4)
C24A—C25A—N28A—C29A29.5 (6)C26B—C25B—N28B—C29B−37.5 (6)
C25A—N28A—C29A—O30A6.7 (6)C25B—N28B—C29B—O30B8.3 (6)
C25A—N28A—C29A—N31A−172.7 (3)C25B—N28B—C29B—N31B−172.3 (3)
O30A—C29A—N31A—C32A−6.0 (6)O30B—C29B—N31B—C32B2.1 (6)
N28A—C29A—N31A—C32A173.4 (3)N28B—C29B—N31B—C32B−177.2 (3)
C29A—N31A—C32A—C33A6.9 (6)C29B—N31B—C32B—C33B−2.3 (6)
C29A—N31A—C32A—C40A−171.6 (3)C29B—N31B—C32B—C40B176.9 (3)
N31A—C32A—C33A—C34A−177.9 (3)N31B—C32B—C33B—C34B178.7 (3)
C40A—C32A—C33A—C34A0.5 (5)C40B—C32B—C33B—C34B−0.4 (5)
C32A—C33A—C34A—C35A0.0 (5)C32B—C33B—C34B—C35B−0.3 (5)
C33A—C34A—C35A—C41A0.0 (6)C33B—C34B—C35B—C41B0.5 (5)
C41A—C36A—C37A—C38A−0.1 (6)C41B—C36B—C37B—C38B1.3 (6)
C36A—C37A—C38A—N39A0.3 (6)C36B—C37B—C38B—N39B−1.6 (6)
C37A—C38A—N39A—C40A0.8 (5)C37B—C38B—N39B—C40B0.4 (5)
C38A—N39A—C40A—C41A−2.1 (5)C38B—N39B—C40B—C41B1.0 (5)
C38A—N39A—C40A—C32A177.6 (3)C38B—N39B—C40B—C32B−179.0 (3)
C33A—C32A—C40A—N39A179.3 (3)C33B—C32B—C40B—N39B−179.0 (3)
N31A—C32A—C40A—N39A−2.1 (4)N31B—C32B—C40B—N39B1.8 (4)
C33A—C32A—C40A—C41A−1.0 (5)C33B—C32B—C40B—C41B1.0 (5)
N31A—C32A—C40A—C41A177.7 (3)N31B—C32B—C40B—C41B−178.2 (3)
N39A—C40A—C41A—C35A−179.4 (3)C37B—C36B—C41B—C40B0.0 (5)
C32A—C40A—C41A—C35A0.9 (5)C37B—C36B—C41B—C35B179.5 (4)
N39A—C40A—C41A—C36A2.2 (5)N39B—C40B—C41B—C36B−1.2 (5)
C32A—C40A—C41A—C36A−177.5 (3)C32B—C40B—C41B—C36B178.8 (3)
C34A—C35A—C41A—C40A−0.4 (5)N39B—C40B—C41B—C35B179.3 (3)
C34A—C35A—C41A—C36A177.8 (4)C32B—C40B—C41B—C35B−0.7 (5)
C37A—C36A—C41A—C40A−1.0 (5)C34B—C35B—C41B—C36B−179.5 (3)
C37A—C36A—C41A—C35A−179.4 (4)C34B—C35B—C41B—C40B0.0 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N11A—H11A···N1A0.74 (4)2.27 (4)2.625 (4)110 (3)
N11A—H11A···O13Ai0.74 (4)2.41 (4)3.101 (3)155 (4)
N14A—H14A···O13Ai0.86 (4)1.97 (4)2.810 (4)166 (3)
N28A—H28A···O30Aii0.78 (4)2.05 (4)2.827 (4)170 (4)
N31A—H31A···O30Aii0.88 (4)2.56 (4)3.293 (4)141 (3)
N31A—H31A···N39A0.88 (4)2.14 (4)2.635 (4)114 (3)
N11B—H11B···N1B0.90 (4)2.13 (4)2.645 (4)116 (3)
N11B—H11B···O30Biii0.90 (4)2.46 (4)3.172 (4)136 (3)
N14B—H14B···O30Biii0.80 (3)1.98 (4)2.772 (4)167 (3)
N28B—H28B···O13Biv0.87 (4)1.94 (4)2.786 (4)161 (4)
N31B—H31B···O13Biv0.90 (4)2.36 (3)3.115 (4)141 (3)
N31B—H31B···N39B0.90 (4)2.14 (3)2.647 (4)115 (3)
Symmetry codes: (i) y, −x+1, z+1/4; (ii) y+1, −x+1, z+1/4; (iii) −y+1, x−1, z−1/4; (iv) −y+1, x, z−1/4.

Experimental details

Crystal data
Chemical formulaC33H26N6O2
Mr538.60
Crystal system, space groupTetragonal, P43
Temperature (K)100
a, c (Å)18.1345 (6), 17.1405 (11)
V (Å3)5636.8 (5)
Z8
Radiation typeMo Kα
µ (mm−1)0.08
Crystal size (mm)0.35 × 0.34 × 0.34
Data collection
DiffractometerBruker APEX CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2001)
Tmin, Tmax0.972, 0.973
No. of measured, independent and
observed [I > 2σ(I)] reflections		65350, 5737, 4589
Rint0.104
(sin θ/λ)max (Å−1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.104, 1.00
No. of reflections5737
No. of parameters767
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.16, −0.17

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N11A—H11A···N1A0.74 (4)2.27 (4)2.625 (4)110 (3)
N11A—H11A···O13Ai0.74 (4)2.41 (4)3.101 (3)155 (4)
N14A—H14A···O13Ai0.86 (4)1.97 (4)2.810 (4)166 (3)
N28A—H28A···O30Aii0.78 (4)2.05 (4)2.827 (4)170 (4)
N31A—H31A···O30Aii0.88 (4)2.56 (4)3.293 (4)141 (3)
N31A—H31A···N39A0.88 (4)2.14 (4)2.635 (4)114 (3)
N11B—H11B···N1B0.90 (4)2.13 (4)2.645 (4)116 (3)
N11B—H11B···O30Biii0.90 (4)2.46 (4)3.172 (4)136 (3)
N14B—H14B···O30Biii0.80 (3)1.98 (4)2.772 (4)167 (3)
N28B—H28B···O13Biv0.87 (4)1.94 (4)2.786 (4)161 (4)
N31B—H31B···O13Biv0.90 (4)2.36 (3)3.115 (4)141 (3)
N31B—H31B···N39B0.90 (4)2.14 (3)2.647 (4)115 (3)
Symmetry codes: (i) y, −x+1, z+1/4; (ii) y+1, −x+1, z+1/4; (iii) −y+1, x−1, z−1/4; (iv) −y+1, x, z−1/4.
 

Acknowledgements

The National Science Foundation is acknowledged for a CAREER award (CHE-1056927) to MAH. The work was supported by the National Institute of Health (G12RR013459). The NMR instrument used for this work was funded by the National Science Foundation (CHE-0821357).

References

First citationBruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
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 First citationSheldrick, G. M. (2001). SADABS. University of Göttingen, Germany.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSmith, P. J., Reddington, M. V. & Wilcox, C. S. (1992). Tetrahedron Lett. 33, 6085–6088.  CrossRef CAS Web of Science Google Scholar
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Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890
Volume 68| Part 1| January 2012| Pages o158-o159
doi:10.1107/S1600536811053220
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