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

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ISSN: 2056-9890

(1R,2R)-N,N′-Bis(4-nitro­phenyl­methyl­ene)­cyclo­hexane-1,2-di­amine

CROSSMARK_Color_square_no_text.svg

aSchool of Chemistry, University of St Andrews, Fife KY16 9ST, Scotland, bDepartment of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen AB24 3UE, Scotland, and cInstituto de Química, Departamento de Química Inorgânica, Universidade Federal do Rio de Janeiro, 21945-970 Rio de Janeiro, RJ, Brazil
*Correspondence e-mail: cg@st-andrews.ac.uk

(Received 29 April 2005; accepted 4 May 2005; online 14 May 2005)

The title compound, C20H20N4O4, crystallizes with two molecules in the asymmetric unit. Each independent mol­ecule exhibits approximate twofold rotation symmetry, but conformational differences between the mol­ecules preclude any higher symmetry.

Comment

Following on from our study of the crystal structures of the di-imines, N,N′-bis(4-nitro­benzyl­idene)­ethane-1,2-di­amine and -propane-1,3-di­amine, obtained from 4-nitro­benz­aldehyde and the appropriate α,ω-di­amino­alkanes (Bomfim et al., 2005[Bomfim, J. A. S., Wardell, J. L., Low, J. N., Skakle, J. M. S. & Glidewell, C. (2005). Acta Cryst. C61, o53-o56.]), we have now studied the structure of the title compound, (I[link]), in which the functional groups are on adjacent carbon sites in a carbocyclic ring.[link]

[Scheme 1]

In the two independent mol­ecules of compound (I[link]) (Fig. 1[link]), the corresponding bond distances and interbond angles are very similar, showing no unusual values. There are clear differences between the single C—N and double C=N bonds (Table 1[link]). The four independent chains which are pendent from the cyclo­hexane rings all occupy equatorial sites (Fig. 1[link]) and all have fairly similar conformations (Table 1[link]), such that each mol­ecule has approximate, although not exact, twofold rotational symmetry. The biggest difference between the two independent mol­ecules arises from the torsion angles between the nitro groups on the benzene rings, 9.8 (2) and 17.6 (2)° in mol­ecule A, but only 0.8 (2) and 1.3 (2)° in mol­ecule B. These differences suffice to preclude the possibility of any additional crystallographic symmetry. There is only one direction-specific interaction between the mol­ecules (Table 2[link]) which might be of significance. Otherwise, the structure consists of isolated pseudosymmetric mol­ecules.

[Figure 1]
Figure 1
The two independent mol­ecules of compound (I[link]), showing the atom-labelling scheme for (a) mol­ecule A and (b) mol­ecule B. Displacement ellipsoids are drawn at the 30% probability level.

Experimental

A mixture of (1R,2R)-cyclo­hexane-1,2-di­amine (0.228 g, 2 mmol) and 4-nitro­benz­aldehyde (0.604 g, 4 mmol) in MeOH (30 ml) was heated under reflux for 30 min. The solution was then cooled to ambient temperature and the solvent was removed. The resulting solid was recrystallized from aqueous ethanol (m.p. 381–382 K). IR (KBr disk) (ν, cm−1): 2924, 2853, 1644, 1602, 1521, 1347, 1140, 1107, 936, 860, 829, 747, 690, 584, 484, 444.

Crystal data
  • C20H20N4O4

  • Mr = 380.40

  • Monoclinic, C2

  • a = 52.275 (3) Å

  • b = 5.3605 (2) Å

  • c = 14.0209 (8) Å

  • β = 104.952 (2)°

  • V = 3795.9 (3) Å3

  • Z = 8

  • Dx = 1.331 Mg m−3

  • Mo Kα radiation

  • Cell parameters from 4774 reflections

  • θ = 3.0–27.7°

  • μ = 0.10 mm−1

  • T = 120 (2) K

  • Needle, yellow

  • 0.38 × 0.06 × 0.04 mm

Data collection
  • Bruker Nonius KappaCCD area-detector diffractometer

  • φ and ω scans

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003[Sheldrick, G. M. (2003). SADABS. Version 2.10. University of Göttingen, Germany.]) Tmin = 0.956, Tmax = 0.996

  • 19 060 measured reflections

  • 4774 independent reflections

  • 2943 reflections with I > 2σ(I)

  • Rint = 0.086

  • θmax = 27.7°

  • h = −67 → 67

  • k = −6 → 6

  • l = −18 → 18

Refinement
  • Refinement on F2

  • R[F2 > 2σ(F2)] = 0.060

  • wR(F2) = 0.124

  • S = 1.02

  • 4774 reflections

  • 505 parameters

  • H-atom parameters constrained

  • w = 1/[σ2(Fo2) + (0.0388P)2 + 2.286P] where P = (Fo2 + 2Fc2)/3

  • (Δ/σ)max < 0.001

  • Δρmax = 0.23 e Å−3

  • Δρmin = −0.26 e Å−3

  • Absolute structure: Friedel pairs merged

Table 1
Selected geometric parameters (Å, °)

C1A—N1A 1.468 (5)
C2A—N2A 1.467 (5)
N1A—C17A 1.254 (5)
N2A—C27A 1.277 (5)
C1B—N1B 1.448 (5)
C2B—N2B 1.460 (5)
N1B—C17B 1.262 (5)
N2B—C27B 1.269 (5)
C2A—C1A—N1A—C17A 108.4 (4)
C1A—N1A—C17A—C11A −176.0 (4)
N1A—C17A—C11A—C12A −178.8 (4)
C13A—C14A—N14A—O14A 10.2 (6)
C1A—C2A—N2A—C27A 137.6 (4)
C2A—N2A—C27A—C21A −173.2 (3)
N2A—C27A—C21A—C26A −172.5 (4)
C23A—C24A—N24A—O24A −15.9 (6)
C2B—C1B—N1B—C17B 136.7 (4)
C1B—N1B—C17B—C11B 177.1 (4)
N1B—C17B—C11B—C12B −176.5 (4)
C13B—C14B—N14B—O14B −2.0 (6)
C1B—C2B—N2B—C27B 122.2 (4)
C2B—N2B—C27B—C21B −173.6 (3)
N2B—C27B—C21B—C26B 177.6 (4)
C23B—C24B—N24B—O24B −2.5 (5)

Table 2
Hydrogen-bonding geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C15B—H15B⋯O25Ai 0.95 2.48 3.392 (6) 161
Symmetry code: (i) 1-x,2+y,1-z.

All H atoms were located in difference maps and then treated as riding atoms with C—H distances of 0.95 (aromatic and CH—), 0.99 (CH2) or 1.00 Å (aliphatic CH), and with Uiso(H) = 1.2Ueq(C). In the absence of significant anomalous scattering, Friedel pairs were merged prior to the final refinement, and the absolute configuration was set according to the known absolute configuration of the (1R,2R)-1,2-di­amino­cyclo­hexane employed in the synthesis.

Data collection: COLLECT (Hooft, 1999[Hooft, R. W. W. (1999). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr and R. M. Sweet, pp. 307-326. New York: Academic Press.]) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); program(s) used to refine structure: OSCAIL (McArdle, 2003[McArdle, P. (2003). OSCAIL for Windows. Version 10. Crystallography Centre, Chemistry Department, NUI Galway, Ireland.]) and SHELXL97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); molecular graphics: PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999[Ferguson, G. (1999). PRPKAPPA. University of Guelph, Canada.]).

Supporting information


Computing details top

Data collection: COLLECT (Hooft, 1999); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS86 (Sheldrick, 1997); program(s) used to refine structure: OSCAIL (McArdle, 2003) and SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999).

(1R,2R)-N,N'-bis(4-nitrophenylmethylene)cyclohexane-1,2-diamine top
Crystal data top
C20H20N4O4F(000) = 1600
Mr = 380.40Dx = 1.331 Mg m3
Monoclinic, C2Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2yCell parameters from 4774 reflections
a = 52.275 (3) Åθ = 3.0–27.7°
b = 5.3605 (2) ŵ = 0.10 mm1
c = 14.0209 (8) ÅT = 120 K
β = 104.952 (2)°Needle, yellow
V = 3795.9 (3) Å30.38 × 0.06 × 0.04 mm
Z = 8
Data collection top
Bruker–Nonius 95mm CCD camera on κ goniostat
diffractometer
4774 independent reflections
Radiation source: Bruker–Nonius FR91 rotating anode2943 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.086
Detector resolution: 9.091 pixels mm-1θmax = 27.7°, θmin = 3.0°
φ and ω scansh = 6767
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
k = 66
Tmin = 0.956, Tmax = 0.996l = 1818
19060 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.060H-atom parameters constrained
wR(F2) = 0.124 w = 1/[σ2(Fo2) + (0.0388P)2 + 2.286P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
4774 reflectionsΔρmax = 0.23 e Å3
505 parametersΔρmin = 0.26 e Å3
1 restraintAbsolute structure: Friedel pairs merged
Primary atom site location: Patterson
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C1A0.50443 (8)0.3481 (8)0.8160 (3)0.0290 (10)
C2A0.49925 (8)0.2985 (9)0.7057 (3)0.0319 (10)
C3A0.52537 (8)0.2552 (9)0.6788 (3)0.0386 (11)
C4A0.54347 (9)0.4825 (9)0.7079 (4)0.0439 (12)
C5A0.54826 (8)0.5380 (9)0.8169 (4)0.0440 (12)
C6A0.52257 (8)0.5728 (9)0.8457 (3)0.0363 (11)
N1A0.47915 (6)0.3949 (7)0.8403 (2)0.0310 (8)
C17A0.47026 (8)0.2321 (8)0.8874 (3)0.0306 (10)
C11A0.44432 (8)0.2550 (8)0.9096 (3)0.0273 (9)
C12A0.43571 (8)0.0703 (8)0.9638 (3)0.0324 (10)
C13A0.41095 (9)0.0825 (9)0.9809 (3)0.0355 (11)
C14A0.39483 (8)0.2809 (8)0.9421 (3)0.0296 (10)
C15A0.40263 (8)0.4671 (9)0.8887 (3)0.0331 (10)
C16A0.42775 (8)0.4562 (8)0.8741 (3)0.0324 (10)
N14A0.36808 (7)0.2899 (7)0.9575 (3)0.0363 (9)
O14A0.36241 (6)0.1425 (6)1.0152 (2)0.0469 (9)
O15A0.35262 (6)0.4470 (6)0.9124 (3)0.0518 (9)
N2A0.48190 (6)0.0800 (7)0.6809 (3)0.0307 (8)
C27A0.46312 (8)0.0903 (8)0.6020 (3)0.0303 (10)
C21A0.44289 (8)0.1038 (8)0.5754 (3)0.0295 (10)
C22A0.44032 (8)0.2850 (8)0.6428 (3)0.0328 (10)
C23A0.41974 (8)0.4565 (9)0.6204 (3)0.0374 (11)
C24A0.40137 (8)0.4370 (8)0.5304 (3)0.0317 (10)
C25A0.40383 (9)0.2639 (10)0.4614 (3)0.0454 (12)
C26A0.42484 (9)0.0984 (10)0.4839 (3)0.0458 (13)
N24A0.37859 (7)0.6069 (8)0.5089 (3)0.0406 (10)
O24A0.37956 (6)0.7927 (7)0.5606 (3)0.0544 (9)
O25A0.35923 (6)0.5499 (7)0.4413 (2)0.0536 (9)
C1B0.74978 (8)0.4396 (9)0.8373 (3)0.0325 (10)
C2B0.76180 (8)0.4089 (8)0.7489 (3)0.0298 (10)
C3B0.78859 (8)0.2805 (9)0.7791 (3)0.0354 (11)
C4B0.80765 (8)0.4167 (9)0.8627 (3)0.0354 (11)
C5B0.79599 (8)0.4411 (9)0.9512 (3)0.0378 (11)
C6B0.76935 (8)0.5748 (9)0.9223 (3)0.0346 (11)
N1B0.72597 (7)0.5891 (7)0.8079 (3)0.0327 (9)
C17B0.70609 (8)0.5181 (8)0.8361 (3)0.0300 (10)
C11B0.68122 (8)0.6610 (8)0.8147 (3)0.0305 (10)
C12B0.66043 (8)0.5796 (9)0.8525 (3)0.0337 (11)
C13B0.63698 (8)0.7128 (9)0.8339 (3)0.0340 (11)
C14B0.63492 (8)0.9244 (8)0.7771 (3)0.0288 (10)
C15B0.65521 (8)1.0133 (9)0.7398 (3)0.0343 (11)
C16B0.67853 (9)0.8809 (9)0.7598 (3)0.0333 (11)
N14B0.60994 (7)1.0675 (8)0.7559 (3)0.0387 (10)
O14B0.59175 (6)0.9868 (7)0.7879 (2)0.0513 (9)
O15B0.60827 (6)1.2569 (7)0.7062 (2)0.0467 (8)
N2B0.74318 (7)0.2571 (7)0.6764 (2)0.0323 (9)
C27B0.73370 (8)0.3451 (8)0.5905 (3)0.0301 (10)
C21B0.71275 (8)0.2157 (8)0.5160 (3)0.0286 (10)
C22B0.70190 (8)0.0074 (8)0.5390 (3)0.0310 (10)
C23B0.68042 (8)0.1134 (8)0.4735 (3)0.0313 (10)
C24B0.67008 (8)0.0033 (8)0.3847 (3)0.0290 (10)
C25B0.68072 (8)0.2215 (9)0.3581 (3)0.0342 (11)
C26B0.70255 (9)0.3261 (8)0.4248 (3)0.0330 (11)
N24B0.64679 (7)0.1063 (8)0.3148 (3)0.0366 (9)
O24B0.63809 (6)0.3038 (6)0.3376 (2)0.0446 (8)
O25B0.63765 (6)0.0013 (7)0.2362 (2)0.0513 (9)
H1A0.51310.19820.85330.035*
H2A0.49010.44650.66840.038*
H3A10.52190.22550.60690.046*
H3A20.53420.10540.71370.046*
H4A10.56060.45020.69230.053*
H4A20.53520.62930.66910.053*
H5A10.55830.39880.85560.053*
H5A20.55910.69120.83310.053*
H6A10.51350.72420.81320.044*
H6A20.52640.59740.91800.044*
H17A0.48070.08810.90970.037*
H12A0.44700.06600.98920.039*
H13A0.40510.04261.01840.043*
H15A0.39100.60060.86230.040*
H16A0.43380.58690.83950.039*
H27A0.46230.22910.55920.036*
H22A0.45280.29200.70530.039*
H23A0.41830.58400.66590.045*
H25A0.39130.25760.39890.055*
H26A0.42690.02010.43610.055*
H1B0.74540.27200.86010.039*
H2B0.76370.57620.71990.036*
H3B10.78620.10750.80000.042*
H3B20.79620.27230.72150.042*
H4B10.81140.58470.84020.042*
H4B20.82460.32390.88230.042*
H5B10.80840.53591.00420.045*
H5B20.79360.27320.97710.045*
H6B10.77200.74770.90180.041*
H6B20.76180.58310.98020.041*
H17B0.70720.36700.87240.036*
H12B0.66240.43210.89130.040*
H13B0.62270.65960.85960.041*
H15B0.65311.16150.70140.041*
H16B0.69290.93960.73610.040*
H27B0.74030.49950.57350.036*
H22B0.70940.08680.60040.037*
H23B0.67290.26410.48940.038*
H25B0.67330.29760.29590.041*
H26B0.71040.47350.40780.040*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1A0.021 (2)0.025 (2)0.037 (3)0.0028 (18)0.0001 (19)0.0048 (19)
C2A0.023 (2)0.035 (3)0.037 (3)0.001 (2)0.007 (2)0.007 (2)
C3A0.032 (3)0.038 (3)0.048 (3)0.002 (2)0.014 (2)0.001 (2)
C4A0.030 (3)0.035 (3)0.071 (4)0.000 (2)0.022 (2)0.008 (3)
C5A0.030 (3)0.037 (3)0.061 (3)0.007 (2)0.003 (2)0.012 (3)
C6A0.032 (2)0.035 (3)0.036 (3)0.007 (2)0.002 (2)0.002 (2)
N1A0.026 (2)0.033 (2)0.032 (2)0.0022 (17)0.0046 (16)0.0004 (18)
C17A0.032 (2)0.027 (3)0.027 (2)0.000 (2)0.0031 (19)0.001 (2)
C11A0.033 (2)0.024 (2)0.024 (2)0.001 (2)0.0052 (18)0.0006 (19)
C12A0.033 (2)0.031 (3)0.032 (2)0.001 (2)0.006 (2)0.001 (2)
C13A0.040 (3)0.035 (3)0.031 (3)0.000 (2)0.009 (2)0.006 (2)
C14A0.031 (2)0.031 (3)0.025 (2)0.001 (2)0.0050 (19)0.007 (2)
C15A0.035 (3)0.034 (3)0.030 (2)0.004 (2)0.006 (2)0.001 (2)
C16A0.034 (3)0.029 (3)0.030 (2)0.001 (2)0.0014 (19)0.002 (2)
N14A0.039 (2)0.036 (2)0.035 (2)0.005 (2)0.0120 (19)0.0043 (19)
O14A0.041 (2)0.059 (2)0.044 (2)0.0001 (17)0.0165 (17)0.0113 (17)
O15A0.045 (2)0.044 (2)0.071 (2)0.0171 (19)0.0233 (19)0.012 (2)
N2A0.0234 (19)0.035 (2)0.032 (2)0.0019 (17)0.0048 (16)0.0005 (17)
C27A0.030 (2)0.031 (2)0.031 (2)0.002 (2)0.010 (2)0.003 (2)
C21A0.029 (2)0.032 (3)0.027 (2)0.001 (2)0.0047 (19)0.002 (2)
C22A0.030 (2)0.039 (3)0.027 (2)0.004 (2)0.0021 (19)0.004 (2)
C23A0.028 (2)0.044 (3)0.040 (3)0.002 (2)0.008 (2)0.003 (2)
C24A0.025 (2)0.037 (3)0.033 (3)0.003 (2)0.008 (2)0.008 (2)
C25A0.044 (3)0.054 (3)0.030 (3)0.006 (3)0.007 (2)0.005 (3)
C26A0.047 (3)0.051 (3)0.033 (3)0.013 (3)0.000 (2)0.005 (3)
N24A0.029 (2)0.044 (3)0.050 (3)0.006 (2)0.012 (2)0.017 (2)
O24A0.042 (2)0.047 (2)0.074 (3)0.0147 (18)0.0148 (19)0.001 (2)
O25A0.0317 (19)0.071 (3)0.051 (2)0.0090 (19)0.0009 (17)0.020 (2)
C1B0.031 (2)0.038 (3)0.029 (2)0.003 (2)0.0067 (19)0.002 (2)
C2B0.032 (2)0.028 (2)0.027 (2)0.002 (2)0.0045 (19)0.001 (2)
C3B0.034 (3)0.037 (3)0.038 (3)0.004 (2)0.014 (2)0.002 (2)
C4B0.032 (2)0.039 (3)0.034 (2)0.000 (2)0.006 (2)0.002 (2)
C5B0.034 (3)0.042 (3)0.033 (2)0.001 (2)0.001 (2)0.000 (2)
C6B0.034 (2)0.041 (3)0.031 (2)0.004 (2)0.012 (2)0.002 (2)
N1B0.029 (2)0.032 (2)0.038 (2)0.0027 (17)0.0111 (17)0.0002 (17)
C17B0.033 (2)0.030 (3)0.026 (2)0.006 (2)0.0046 (19)0.0029 (19)
C11B0.028 (2)0.037 (3)0.026 (2)0.003 (2)0.0073 (19)0.006 (2)
C12B0.034 (3)0.035 (3)0.033 (3)0.002 (2)0.011 (2)0.005 (2)
C13B0.030 (2)0.039 (3)0.033 (3)0.006 (2)0.008 (2)0.002 (2)
C14B0.020 (2)0.036 (3)0.028 (2)0.004 (2)0.0014 (17)0.003 (2)
C15B0.031 (2)0.037 (3)0.034 (3)0.001 (2)0.007 (2)0.004 (2)
C16B0.031 (2)0.039 (3)0.032 (2)0.002 (2)0.010 (2)0.000 (2)
N14B0.030 (2)0.050 (3)0.033 (2)0.003 (2)0.0036 (18)0.006 (2)
O14B0.0289 (18)0.069 (2)0.059 (2)0.0013 (18)0.0175 (17)0.006 (2)
O15B0.0394 (19)0.043 (2)0.056 (2)0.0021 (17)0.0112 (17)0.0052 (19)
N2B0.036 (2)0.032 (2)0.028 (2)0.0038 (18)0.0066 (17)0.0012 (18)
C27B0.032 (3)0.030 (3)0.030 (2)0.001 (2)0.011 (2)0.001 (2)
C21B0.029 (2)0.035 (3)0.023 (2)0.002 (2)0.0087 (19)0.002 (2)
C22B0.034 (2)0.034 (3)0.025 (2)0.004 (2)0.0078 (19)0.001 (2)
C23B0.031 (2)0.034 (3)0.029 (2)0.001 (2)0.009 (2)0.002 (2)
C24B0.028 (2)0.036 (3)0.023 (2)0.002 (2)0.0063 (18)0.0020 (19)
C25B0.038 (3)0.039 (3)0.024 (2)0.007 (2)0.004 (2)0.004 (2)
C26B0.039 (3)0.029 (3)0.030 (2)0.003 (2)0.007 (2)0.006 (2)
N24B0.029 (2)0.045 (3)0.033 (2)0.002 (2)0.0046 (18)0.005 (2)
O24B0.042 (2)0.041 (2)0.047 (2)0.0096 (17)0.0055 (16)0.0015 (17)
O25B0.050 (2)0.058 (2)0.0364 (19)0.0061 (18)0.0056 (16)0.0076 (18)
Geometric parameters (Å, º) top
C1A—N1A1.468 (5)C1B—N1B1.448 (5)
C1A—C6A1.523 (6)C1B—C2B1.537 (5)
C1A—C2A1.524 (6)C1B—C6B1.537 (6)
C1A—H1A1.00C1B—H1B1.00
C2A—N2A1.467 (5)C2B—N2B1.460 (5)
C2A—C3A1.524 (5)C2B—C3B1.519 (6)
C2A—H2A1.00C2B—H2B1.00
C3A—C4A1.532 (6)C3B—C4B1.516 (6)
C3A—H3A10.99C3B—H3B10.99
C3A—H3A20.99C3B—H3B20.99
C4A—C5A1.514 (6)C4B—C5B1.522 (5)
C4A—H4A10.99C4B—H4B10.99
C4A—H4A20.99C4B—H4B20.99
C5A—C6A1.510 (6)C5B—C6B1.525 (6)
C5A—H5A10.99C5B—H5B10.99
C5A—H5A20.99C5B—H5B20.99
C6A—H6A10.99C6B—H6B10.99
C6A—H6A20.99C6B—H6B20.99
N1A—C17A1.254 (5)N1B—C17B1.262 (5)
C17A—C11A1.473 (5)C17B—C11B1.472 (6)
C17A—H17A0.95C17B—H17B0.95
C11A—C12A1.391 (6)C11B—C16B1.395 (6)
C11A—C16A1.393 (6)C11B—C12B1.396 (5)
C12A—C13A1.378 (6)C12B—C13B1.384 (6)
C12A—H12A0.95C12B—H12B0.95
C13A—C14A1.379 (6)C13B—C14B1.374 (6)
C13A—H13A0.95C13B—H13B0.95
C14A—C15A1.371 (6)C14B—C15B1.383 (5)
C14A—N14A1.470 (5)C14B—N14B1.477 (5)
C15A—C16A1.382 (5)C15B—C16B1.375 (6)
C15A—H15A0.95C15B—H15B0.95
C16A—H16A0.95C16B—H16B0.95
N14A—O14A1.220 (4)N14B—O15B1.222 (5)
N14A—O15A1.224 (5)N14B—O14B1.230 (4)
N2A—C27A1.277 (5)N2B—C27B1.269 (5)
C27A—C21A1.462 (6)C27B—C21B1.477 (6)
C27A—H27A0.95C27B—H27B0.95
C21A—C26A1.382 (6)C21B—C26B1.384 (5)
C21A—C22A1.386 (6)C21B—C22B1.396 (6)
C22A—C23A1.388 (6)C22B—C23B1.376 (6)
C22A—H22A0.95C22B—H22B0.95
C23A—C24A1.379 (6)C23B—C24B1.374 (6)
C23A—H23A0.95C23B—H23B0.95
C24A—C25A1.369 (6)C24B—C25B1.387 (6)
C24A—N24A1.468 (5)C24B—N24B1.474 (5)
C25A—C26A1.383 (6)C25B—C26B1.393 (6)
C25A—H25A0.95C25B—H25B0.95
C26A—H26A0.95C26B—H26B0.95
N24A—O24A1.225 (5)N24B—O25B1.226 (4)
N24A—O25A1.234 (5)N24B—O24B1.227 (5)
N1A—C1A—C6A109.6 (3)N1B—C1B—C2B109.3 (3)
N1A—C1A—C2A109.3 (3)N1B—C1B—C6B108.1 (4)
C6A—C1A—C2A110.5 (3)C2B—C1B—C6B110.3 (3)
N1A—C1A—H1A109.1N1B—C1B—H1B109.7
C6A—C1A—H1A109.1C2B—C1B—H1B109.7
C2A—C1A—H1A109.1C6B—C1B—H1B109.7
N2A—C2A—C1A108.4 (3)N2B—C2B—C3B110.0 (3)
N2A—C2A—C3A111.0 (3)N2B—C2B—C1B106.5 (3)
C1A—C2A—C3A110.0 (3)C3B—C2B—C1B111.3 (3)
N2A—C2A—H2A109.1N2B—C2B—H2B109.7
C1A—C2A—H2A109.1C3B—C2B—H2B109.7
C3A—C2A—H2A109.1C1B—C2B—H2B109.7
C2A—C3A—C4A110.1 (4)C4B—C3B—C2B111.8 (4)
C2A—C3A—H3A1109.6C4B—C3B—H3B1109.2
C4A—C3A—H3A1109.6C2B—C3B—H3B1109.2
C2A—C3A—H3A2109.6C4B—C3B—H3B2109.2
C4A—C3A—H3A2109.6C2B—C3B—H3B2109.2
H3A1—C3A—H3A2108.1H3B1—C3B—H3B2107.9
C5A—C4A—C3A110.8 (4)C3B—C4B—C5B110.5 (3)
C5A—C4A—H4A1109.5C3B—C4B—H4B1109.5
C3A—C4A—H4A1109.5C5B—C4B—H4B1109.5
C5A—C4A—H4A2109.5C3B—C4B—H4B2109.5
C3A—C4A—H4A2109.5C5B—C4B—H4B2109.5
H4A1—C4A—H4A2108.1H4B1—C4B—H4B2108.1
C6A—C5A—C4A111.6 (4)C4B—C5B—C6B110.7 (4)
C6A—C5A—H5A1109.3C4B—C5B—H5B1109.5
C4A—C5A—H5A1109.3C6B—C5B—H5B1109.5
C6A—C5A—H5A2109.3C4B—C5B—H5B2109.5
C4A—C5A—H5A2109.3C6B—C5B—H5B2109.5
H5A1—C5A—H5A2108.0H5B1—C5B—H5B2108.1
C5A—C6A—C1A111.3 (4)C5B—C6B—C1B111.4 (4)
C5A—C6A—H6A1109.4C5B—C6B—H6B1109.4
C1A—C6A—H6A1109.4C1B—C6B—H6B1109.4
C5A—C6A—H6A2109.4C5B—C6B—H6B2109.4
C1A—C6A—H6A2109.4C1B—C6B—H6B2109.4
H6A1—C6A—H6A2108.0H6B1—C6B—H6B2108.0
C17A—N1A—C1A118.8 (4)C17B—N1B—C1B117.5 (4)
N1A—C17A—C11A122.7 (4)N1B—C17B—C11B122.3 (4)
N1A—C17A—H17A118.7N1B—C17B—H17B118.8
C11A—C17A—H17A118.7C11B—C17B—H17B118.8
C12A—C11A—C16A119.2 (4)C16B—C11B—C12B119.8 (4)
C12A—C11A—C17A120.1 (4)C16B—C11B—C17B120.7 (4)
C16A—C11A—C17A120.7 (4)C12B—C11B—C17B119.6 (4)
C13A—C12A—C11A120.8 (4)C13B—C12B—C11B120.4 (4)
C13A—C12A—H12A119.6C13B—C12B—H12B119.8
C11A—C12A—H12A119.6C11B—C12B—H12B119.8
C12A—C13A—C14A118.3 (4)C14B—C13B—C12B117.9 (4)
C12A—C13A—H13A120.8C14B—C13B—H13B121.0
C14A—C13A—H13A120.8C12B—C13B—H13B121.0
C15A—C14A—C13A122.6 (4)C13B—C14B—C15B123.4 (4)
C15A—C14A—N14A119.0 (4)C13B—C14B—N14B118.6 (4)
C13A—C14A—N14A118.4 (4)C15B—C14B—N14B118.0 (4)
C14A—C15A—C16A118.6 (4)C16B—C15B—C14B118.1 (4)
C14A—C15A—H15A120.7C16B—C15B—H15B120.9
C16A—C15A—H15A120.7C14B—C15B—H15B120.9
C15A—C16A—C11A120.5 (4)C15B—C16B—C11B120.4 (4)
C15A—C16A—H16A119.8C15B—C16B—H16B119.8
C11A—C16A—H16A119.8C11B—C16B—H16B119.8
O14A—N14A—O15A123.1 (4)O15B—N14B—O14B123.5 (4)
O14A—N14A—C14A118.6 (4)O15B—N14B—C14B118.4 (4)
O15A—N14A—C14A118.2 (4)O14B—N14B—C14B118.1 (4)
C27A—N2A—C2A117.4 (4)C27B—N2B—C2B118.7 (4)
N2A—C27A—C21A122.3 (4)N2B—C27B—C21B122.2 (4)
N2A—C27A—H27A118.8N2B—C27B—H27B118.9
C21A—C27A—H27A118.8C21B—C27B—H27B118.9
C26A—C21A—C22A119.0 (4)C26B—C21B—C22B119.8 (4)
C26A—C21A—C27A119.9 (4)C26B—C21B—C27B119.4 (4)
C22A—C21A—C27A121.0 (4)C22B—C21B—C27B120.7 (4)
C21A—C22A—C23A121.1 (4)C23B—C22B—C21B120.7 (4)
C21A—C22A—H22A119.5C23B—C22B—H22B119.7
C23A—C22A—H22A119.5C21B—C22B—H22B119.7
C24A—C23A—C22A118.2 (4)C24B—C23B—C22B118.6 (4)
C24A—C23A—H23A120.9C24B—C23B—H23B120.7
C22A—C23A—H23A120.9C22B—C23B—H23B120.7
C25A—C24A—C23A121.9 (4)C23B—C24B—C25B122.5 (4)
C25A—C24A—N24A119.6 (4)C23B—C24B—N24B119.1 (4)
C23A—C24A—N24A118.5 (4)C25B—C24B—N24B118.5 (4)
C24A—C25A—C26A119.1 (4)C24B—C25B—C26B118.3 (4)
C24A—C25A—H25A120.4C24B—C25B—H25B120.8
C26A—C25A—H25A120.4C26B—C25B—H25B120.8
C21A—C26A—C25A120.7 (4)C21B—C26B—C25B120.1 (4)
C21A—C26A—H26A119.7C21B—C26B—H26B119.9
C25A—C26A—H26A119.7C25B—C26B—H26B119.9
O24A—N24A—O25A123.9 (4)O25B—N24B—O24B123.7 (4)
O24A—N24A—C24A118.4 (4)O25B—N24B—C24B118.3 (4)
O25A—N24A—C24A117.7 (4)O24B—N24B—C24B117.9 (4)
N1A—C1A—C2A—N2A59.7 (4)N1B—C1B—C2B—N2B67.0 (4)
C6A—C1A—C2A—N2A179.6 (3)C6B—C1B—C2B—N2B174.2 (4)
N1A—C1A—C2A—C3A178.8 (3)N1B—C1B—C2B—C3B173.1 (4)
C6A—C1A—C2A—C3A58.1 (4)C6B—C1B—C2B—C3B54.3 (5)
N2A—C2A—C3A—C4A178.4 (4)N2B—C2B—C3B—C4B173.5 (3)
C1A—C2A—C3A—C4A58.5 (5)C1B—C2B—C3B—C4B55.7 (5)
C2A—C3A—C4A—C5A57.2 (5)C2B—C3B—C4B—C5B56.8 (5)
C3A—C4A—C5A—C6A55.6 (5)C3B—C4B—C5B—C6B57.0 (5)
C4A—C5A—C6A—C1A55.3 (5)C4B—C5B—C6B—C1B57.0 (5)
N1A—C1A—C6A—C5A176.9 (3)N1B—C1B—C6B—C5B174.7 (3)
C2A—C1A—C6A—C5A56.4 (5)C2B—C1B—C6B—C5B55.3 (5)
C6A—C1A—N1A—C17A130.3 (4)C2B—C1B—N1B—C17B136.7 (4)
C2A—C1A—N1A—C17A108.4 (4)C6B—C1B—N1B—C17B103.2 (4)
C1A—N1A—C17A—C11A176.0 (4)C1B—N1B—C17B—C11B177.1 (4)
N1A—C17A—C11A—C12A178.8 (4)N1B—C17B—C11B—C16B1.4 (6)
N1A—C17A—C11A—C16A3.4 (6)N1B—C17B—C11B—C12B176.5 (4)
C16A—C11A—C12A—C13A1.1 (6)C16B—C11B—C12B—C13B1.5 (6)
C17A—C11A—C12A—C13A176.7 (4)C17B—C11B—C12B—C13B179.5 (4)
C11A—C12A—C13A—C14A0.7 (6)C11B—C12B—C13B—C14B0.4 (6)
C12A—C13A—C14A—C15A0.9 (6)C12B—C13B—C14B—C15B1.5 (6)
C12A—C13A—C14A—N14A178.0 (4)C12B—C13B—C14B—N14B179.5 (4)
C13A—C14A—C15A—C16A0.7 (6)C13B—C14B—C15B—C16B0.7 (6)
N14A—C14A—C15A—C16A179.6 (4)N14B—C14B—C15B—C16B179.7 (4)
C14A—C15A—C16A—C11A2.5 (6)C14B—C15B—C16B—C11B1.2 (6)
C12A—C11A—C16A—C15A2.7 (6)C12B—C11B—C16B—C15B2.3 (6)
C17A—C11A—C16A—C15A175.0 (4)C17B—C11B—C16B—C15B179.8 (4)
C15A—C14A—N14A—O14A170.8 (4)C13B—C14B—N14B—O15B179.3 (4)
C13A—C14A—N14A—O14A10.2 (6)C15B—C14B—N14B—O15B0.2 (6)
C15A—C14A—N14A—O15A8.5 (6)C13B—C14B—N14B—O14B2.0 (6)
C13A—C14A—N14A—O15A170.5 (4)C15B—C14B—N14B—O14B179.0 (4)
C1A—C2A—N2A—C27A137.6 (4)C3B—C2B—N2B—C27B117.1 (4)
C3A—C2A—N2A—C27A101.5 (4)C1B—C2B—N2B—C27B122.2 (4)
C2A—N2A—C27A—C21A173.2 (3)C2B—N2B—C27B—C21B173.6 (3)
N2A—C27A—C21A—C26A172.5 (4)N2B—C27B—C21B—C26B177.6 (4)
N2A—C27A—C21A—C22A11.9 (6)N2B—C27B—C21B—C22B2.1 (6)
C26A—C21A—C22A—C23A1.2 (6)C26B—C21B—C22B—C23B2.8 (6)
C27A—C21A—C22A—C23A174.5 (4)C27B—C21B—C22B—C23B172.7 (4)
C21A—C22A—C23A—C24A2.1 (6)C21B—C22B—C23B—C24B0.8 (6)
C22A—C23A—C24A—C25A3.8 (6)C22B—C23B—C24B—C25B1.0 (6)
C22A—C23A—C24A—N24A176.0 (4)C22B—C23B—C24B—N24B179.0 (3)
C23A—C24A—C25A—C26A2.2 (7)C23B—C24B—C25B—C26B0.7 (6)
N24A—C24A—C25A—C26A177.6 (4)N24B—C24B—C25B—C26B179.3 (4)
C22A—C21A—C26A—C25A2.9 (7)C22B—C21B—C26B—C25B3.1 (6)
C27A—C21A—C26A—C25A172.9 (4)C27B—C21B—C26B—C25B172.4 (4)
C24A—C25A—C26A—C21A1.2 (7)C24B—C25B—C26B—C21B1.4 (6)
C25A—C24A—N24A—O24A164.3 (4)C23B—C24B—N24B—O25B179.4 (4)
C23A—C24A—N24A—O24A15.9 (6)C25B—C24B—N24B—O25B0.6 (5)
C25A—C24A—N24A—O25A17.7 (6)C23B—C24B—N24B—O24B2.5 (5)
C23A—C24A—N24A—O25A162.1 (4)C25B—C24B—N24B—O24B177.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C15B—H15B···O25Ai0.952.483.392 (6)161
Symmetry code: (i) x+1, y+2, z+1.
 

Acknowledgements

X-ray data were collected at the EPSRC X-ray Crystallographic Service, University of Southampton, England; the authors thank the staff for all their help and advice. JLW thanks CNPq and FAPERJ for financial support.

References

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