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The structure determination of the tetra­aza macrocyclic title compound, C24H46N6, shows that its mol­ecule represents a meso-isomer; it occupies a special position about the crystallographic inversion centre. The pendent ethyl­cyano arms are oriented above and below the N4 plane and are directed away from the central cavity.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680100784X/ya6025sup1.cif
Contains datablocks general, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680100784X/ya6025Isup2.hkl
Contains datablock I

CCDC reference: 170303

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.045
  • wR factor = 0.143
  • Data-to-parameter ratio = 26.7

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
ABSMU_01 Alert C The ratio of given/expected absorption coefficient lies outside the range 0.99 <> 1.01 Calculated value of mu = 0.067 Value of mu given = 0.070
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1996); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN for Windows (Molecular Structure Corporation, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97.

(I) top
Crystal data top
C24H46N6F(000) = 464
Mr = 418.67Dx = 1.107 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71069 Å
Hall symbol: P 2ybcCell parameters from 23 reflections
a = 7.974 (3) Åθ = 7.4–10.4°
b = 17.685 (4) ŵ = 0.07 mm1
c = 9.007 (6) ÅT = 173 K
β = 98.74 (4)°Block, colourless
V = 1255.4 (10) Å30.48 × 0.44 × 0.40 mm
Z = 2
Data collection top
Rigaku AFC-7R
diffractometer
Rint = 0.013
Radiation source: Rotating anodeθmax = 30.0°, θmin = 3.2°
Graphite monochromatorh = 011
ω–2θ scansk = 024
4008 measured reflectionsl = 1212
3652 independent reflections3 standard reflections every 400 reflections
2496 reflections with I > 2σ(I) intensity decay: 1.6%
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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0749P)2 + 0.2245P]
where P = (Fo2 + 2Fc2)/3
3652 reflections(Δ/σ)max < 0.001
137 parametersΔρmax = 0.28 e Å3
0 restraintsΔρmin = 0.22 e Å3
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic)

treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.36036 (11)0.41055 (5)0.14026 (11)0.0220 (2)
N40.59827 (11)0.53730 (5)0.16281 (10)0.0219 (2)
H4N0.55430.55220.06580.025*
N120.8169 (2)0.28424 (10)0.45658 (17)0.0601 (4)
C20.31546 (14)0.48660 (7)0.18771 (13)0.0244 (2)
H2A0.23640.48110.26180.0438 (10)*
H2B0.25350.51310.09920.0438 (10)*
C30.46374 (14)0.53685 (7)0.25718 (13)0.0265 (2)
H30.51170.51520.35720.0350 (8)*
C3'0.38959 (19)0.61482 (9)0.2834 (2)0.0461 (4)
H3A0.48080.64870.32780.0526 (11)*
H3B0.30560.60990.35170.0526 (11)*
H3C0.33490.63570.18730.0526 (11)*
C50.74362 (15)0.58700 (7)0.21402 (13)0.0266 (2)
H50.70060.63870.23260.0350 (8)*
C5'0.84607 (18)0.55706 (10)0.35956 (15)0.0426 (4)
H5A0.77270.55390.43730.0526 (11)*
H5B0.94080.59140.39280.0526 (11)*
H5C0.89030.50670.34180.0526 (11)*
C60.85799 (14)0.59193 (7)0.09233 (13)0.0255 (2)
H6A0.88980.53980.06810.0438 (10)*
H6B0.96360.61820.13610.0438 (10)*
C70.78791 (14)0.63197 (6)0.05734 (14)0.0251 (2)
C7'0.93405 (16)0.63931 (8)0.15048 (16)0.0338 (3)
H7A0.97180.58880.17570.0526 (11)*
H7B1.02890.66650.09190.0526 (11)*
H7C0.89440.66730.24310.0526 (11)*
C7''0.73113 (18)0.71188 (7)0.01892 (18)0.0363 (3)
H7D0.63830.70810.04060.0526 (11)*
H7E0.69210.73960.11200.0526 (11)*
H7F0.82680.73880.03910.0526 (11)*
C100.45731 (14)0.36813 (7)0.26500 (13)0.0287 (3)
H10A0.39760.32040.28080.0438 (10)*
H10B0.46630.39830.35850.0438 (10)*
C110.63533 (15)0.35045 (8)0.22959 (15)0.0308 (3)
H11A0.62570.31750.13990.0438 (10)*
H11B0.69100.39810.20610.0438 (10)*
C120.73976 (17)0.31303 (8)0.35538 (16)0.0357 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0184 (4)0.0228 (4)0.0248 (4)0.0001 (3)0.0034 (3)0.0033 (3)
N40.0208 (4)0.0248 (4)0.0197 (4)0.0030 (3)0.0019 (3)0.0014 (3)
N120.0558 (9)0.0729 (11)0.0495 (8)0.0318 (8)0.0010 (7)0.0124 (7)
C20.0216 (5)0.0264 (5)0.0256 (5)0.0004 (4)0.0052 (4)0.0016 (4)
C30.0257 (5)0.0332 (6)0.0211 (5)0.0038 (4)0.0053 (4)0.0049 (4)
C3'0.0362 (7)0.0441 (8)0.0614 (10)0.0064 (6)0.0187 (7)0.0289 (7)
C50.0233 (5)0.0288 (6)0.0268 (5)0.0042 (4)0.0004 (4)0.0059 (4)
C5'0.0337 (7)0.0640 (10)0.0268 (6)0.0077 (6)0.0057 (5)0.0013 (6)
C60.0188 (5)0.0268 (6)0.0300 (6)0.0025 (4)0.0010 (4)0.0037 (4)
C70.0202 (5)0.0222 (5)0.0336 (6)0.0024 (4)0.0060 (4)0.0002 (4)
C7'0.0260 (6)0.0337 (6)0.0441 (7)0.0068 (5)0.0128 (5)0.0012 (5)
C7''0.0366 (7)0.0212 (6)0.0515 (8)0.0002 (5)0.0075 (6)0.0017 (5)
C100.0241 (5)0.0344 (6)0.0286 (6)0.0052 (4)0.0069 (4)0.0097 (5)
C110.0240 (5)0.0345 (6)0.0345 (6)0.0065 (5)0.0064 (5)0.0078 (5)
C120.0308 (6)0.0362 (7)0.0401 (7)0.0093 (5)0.0054 (5)0.0030 (6)
Geometric parameters (Å, º) top
N1—C21.4719 (15)C5—C61.5311 (18)
N1—C7i1.5010 (15)C5—C5'1.5299 (19)
N1—C101.4693 (16)C6—C71.5498 (18)
N4—C31.4665 (16)C7—N1i1.5010 (15)
N4—C51.4718 (15)C7—C7''1.5393 (17)
N12—C121.139 (2)C7—C7'1.5414 (17)
C2—C31.5344 (17)C10—C111.5337 (17)
C3—C3'1.5326 (19)C11—C121.4589 (19)
C10—N1—C2111.56 (10)C5—C6—C7118.26 (10)
C10—N1—C7i114.06 (9)N1i—C7—C7''109.60 (10)
C2—N1—C7i113.22 (9)N1i—C7—C7'112.02 (10)
C3—N4—C5115.61 (9)C7''—C7—C7'108.52 (10)
N1—C2—C3116.18 (10)N1i—C7—C6110.88 (9)
N4—C3—C3'114.69 (11)C7''—C7—C6107.66 (11)
N4—C3—C2110.67 (9)C7'—C7—C6108.02 (10)
C3'—C3—C2107.00 (10)N1—C10—C11109.95 (10)
N4—C5—C6109.64 (9)C12—C11—C10111.60 (11)
N4—C5—C5'110.76 (11)N12—C12—C11177.59 (15)
C6—C5—C5'109.54 (11)
Symmetry code: (i) x+1, y+1, z.
 

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