trans-(3S,5S,10R,12R)-1,8-Bis(2-cyano­ethyl)-C-meso-3,5,7,7,10,12,14,14-octa­methyl-1,4,8,11-tetra­aza­cyclo­tetra­decane

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.

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


 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

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)

Crystal data

C24H46N6	F(000) = 464
Mr = 418.67	Dx = 1.107 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: P 2ybc	Cell parameters from 23 reflections
a = 7.974 (3) Å	θ = 7.4–10.4°
b = 17.685 (4) Å	µ = 0.07 mm^−1
c = 9.007 (6) Å	T = 173 K
β = 98.74 (4)°	Block, colourless
V = 1255.4 (10) Å^3	0.48 × 0.44 × 0.40 mm
Z = 2

Data collection

Rigaku AFC-7R diffractometer	Rint = 0.013
Radiation source: Rotating anode	θmax = 30.0°, θmin = 3.2°
Graphite monochromator	h = 0→11
ω–2θ scans	k = 0→24
4008 measured reflections	l = −12→12
3652 independent reflections	3 standard reflections every 400 reflections
2496 reflections with I > 2σ(I)	intensity decay: 1.6%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.143	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0749P)^2 + 0.2245P] where P = (Fo^2 + 2Fc^2)/3
3652 reflections	(Δ/σ)max < 0.001
137 parameters	Δρmax = 0.28 e Å^−3
0 restraints	Δρmin = −0.22 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
N1	0.36036 (11)	0.41055 (5)	0.14026 (11)	0.0220 (2)
N4	0.59827 (11)	0.53730 (5)	0.16281 (10)	0.0219 (2)
H4N	0.5543	0.5522	0.0658	0.025*
N12	0.8169 (2)	0.28424 (10)	0.45658 (17)	0.0601 (4)
C2	0.31546 (14)	0.48660 (7)	0.18771 (13)	0.0244 (2)
H2A	0.2364	0.4811	0.2618	0.0438 (10)*
H2B	0.2535	0.5131	0.0992	0.0438 (10)*
C3	0.46374 (14)	0.53685 (7)	0.25718 (13)	0.0265 (2)
H3	0.5117	0.5152	0.3572	0.0350 (8)*
C3'	0.38959 (19)	0.61482 (9)	0.2834 (2)	0.0461 (4)
H3A	0.4808	0.6487	0.3278	0.0526 (11)*
H3B	0.3056	0.6099	0.3517	0.0526 (11)*
H3C	0.3349	0.6357	0.1873	0.0526 (11)*
C5	0.74362 (15)	0.58700 (7)	0.21402 (13)	0.0266 (2)
H5	0.7006	0.6387	0.2326	0.0350 (8)*
C5'	0.84607 (18)	0.55706 (10)	0.35956 (15)	0.0426 (4)
H5A	0.7727	0.5539	0.4373	0.0526 (11)*
H5B	0.9408	0.5914	0.3928	0.0526 (11)*
H5C	0.8903	0.5067	0.3418	0.0526 (11)*
C6	0.85799 (14)	0.59193 (7)	0.09233 (13)	0.0255 (2)
H6A	0.8898	0.5398	0.0681	0.0438 (10)*
H6B	0.9636	0.6182	0.1361	0.0438 (10)*
C7	0.78791 (14)	0.63197 (6)	−0.05734 (14)	0.0251 (2)
C7'	0.93405 (16)	0.63931 (8)	−0.15048 (16)	0.0338 (3)
H7A	0.9718	0.5888	−0.1757	0.0526 (11)*
H7B	1.0289	0.6665	−0.0919	0.0526 (11)*
H7C	0.8944	0.6673	−0.2431	0.0526 (11)*
C7''	0.73113 (18)	0.71188 (7)	−0.01892 (18)	0.0363 (3)
H7D	0.6383	0.7081	0.0406	0.0526 (11)*
H7E	0.6921	0.7396	−0.1120	0.0526 (11)*
H7F	0.8268	0.7388	0.0391	0.0526 (11)*
C10	0.45731 (14)	0.36813 (7)	0.26500 (13)	0.0287 (3)
H10A	0.3976	0.3204	0.2808	0.0438 (10)*
H10B	0.4663	0.3983	0.3585	0.0438 (10)*
C11	0.63533 (15)	0.35045 (8)	0.22959 (15)	0.0308 (3)
H11A	0.6257	0.3175	0.1399	0.0438 (10)*
H11B	0.6910	0.3981	0.2061	0.0438 (10)*
C12	0.73976 (17)	0.31303 (8)	0.35538 (16)	0.0357 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0184 (4)	0.0228 (4)	0.0248 (4)	0.0001 (3)	0.0034 (3)	0.0033 (3)
N4	0.0208 (4)	0.0248 (4)	0.0197 (4)	−0.0030 (3)	0.0019 (3)	−0.0014 (3)
N12	0.0558 (9)	0.0729 (11)	0.0495 (8)	0.0318 (8)	0.0010 (7)	0.0124 (7)
C2	0.0216 (5)	0.0264 (5)	0.0256 (5)	−0.0004 (4)	0.0052 (4)	−0.0016 (4)
C3	0.0257 (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)
C5	0.0233 (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)
C6	0.0188 (5)	0.0268 (6)	0.0300 (6)	−0.0025 (4)	0.0010 (4)	−0.0037 (4)
C7	0.0202 (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)
C10	0.0241 (5)	0.0344 (6)	0.0286 (6)	0.0052 (4)	0.0069 (4)	0.0097 (5)
C11	0.0240 (5)	0.0345 (6)	0.0345 (6)	0.0065 (5)	0.0064 (5)	0.0078 (5)
C12	0.0308 (6)	0.0362 (7)	0.0401 (7)	0.0093 (5)	0.0054 (5)	0.0030 (6)

Geometric parameters (Å, º)

N1—C2	1.4719 (15)	C5—C6	1.5311 (18)
N1—C7^i	1.5010 (15)	C5—C5'	1.5299 (19)
N1—C10	1.4693 (16)	C6—C7	1.5498 (18)
N4—C3	1.4665 (16)	C7—N1^i	1.5010 (15)
N4—C5	1.4718 (15)	C7—C7''	1.5393 (17)
N12—C12	1.139 (2)	C7—C7'	1.5414 (17)
C2—C3	1.5344 (17)	C10—C11	1.5337 (17)
C3—C3'	1.5326 (19)	C11—C12	1.4589 (19)
C10—N1—C2	111.56 (10)	C5—C6—C7	118.26 (10)
C10—N1—C7^i	114.06 (9)	N1^i—C7—C7''	109.60 (10)
C2—N1—C7^i	113.22 (9)	N1^i—C7—C7'	112.02 (10)
C3—N4—C5	115.61 (9)	C7''—C7—C7'	108.52 (10)
N1—C2—C3	116.18 (10)	N1^i—C7—C6	110.88 (9)
N4—C3—C3'	114.69 (11)	C7''—C7—C6	107.66 (11)
N4—C3—C2	110.67 (9)	C7'—C7—C6	108.02 (10)
C3'—C3—C2	107.00 (10)	N1—C10—C11	109.95 (10)
N4—C5—C6	109.64 (9)	C12—C11—C10	111.60 (11)
N4—C5—C5'	110.76 (11)	N12—C12—C11	177.59 (15)
C6—C5—C5'	109.54 (11)

Symmetry code: (i) −x+1, −y+1, −z.