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Acta Cryst. (2012). E68, o158-o159    [ doi:10.1107/S1600536811053220 ]

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

A. Pramanik, T. H. Russ, D. R. Powell and M. A. Hossain

Abstract top

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.

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)
graphiteRint = 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 reflectionsθmax = 26.0°
Refinement top
R[F2 > 2σ(F2)] = 0.046H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.104Δρmax = 0.16 e Å−3
S = 1.00Δρmin = −0.17 e Å−3
5737 reflectionsAbsolute structure: ?
767 parametersFlack parameter: ?
1 restraintRogers parameter: ?
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, °) 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, °) 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.
Table 1
Hydrogen-bond geometry (Å, °) 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 top

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
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