3,3′-(5,5,7,12,12,14-Hexa­methyl-1,4,8,11-tetra­azacyclo­tetra­decane-1,8-diyl)di­propanonitrile methanol disolvate

Hao, C.-J.; Zhang, Y.-H.

doi:10.1107/S1600536810013073

organic compounds

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Volume 66| Part 5| May 2010| Page o1089

https://doi.org/10.1107/S1600536810013073

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3,3′-(5,5,7,12,12,14-Hexamethyl-1,4,8,11-tetraazacyclotetradecane-1,8-diyl)dipropanonitrile methanol disolvate

Cheng-Jun Hao ^a ^* and Yan-Hua Zhang ^b

^aCollege of Chemistry and Chemical Engineering, Pingdingshan University, Pingdingshan 467000, People's Republic of China, and ^bDepartment of Chemistry and Chemical Engineering, Henan University of Urban Construction, Pingdingshan 467044, People's Republic of China
^*Correspondence e-mail: haochengjun2008@163.com

(Received 25 March 2010; accepted 8 April 2010; online 17 April 2010)

The asymmetric unit of the title compound, C₂₂H₄₂N₆·2CH₄O, comprises one half of a 14-membered tetraazacyclotetradecane macrocycle with cyanoethyl substituents on one of the N atoms and a methanol solvent molecule. The macrocycle lies about an inversion centre. The cyanoethyl substituents are oriented so that the cyano groups lie over opposite faces of the central cavity of the macrocycle. The methanol solvate molecules lie away from the cavity of the macrocycle and are linked to the macrocycles via O—H⋯N hydrogen bonds.

Related literature

For background to macrocycles with pendant coordinating groups, see: Madeyski et al. (1984 ); Hay et al. (1987 ); Melson (1979 ). For a related structure, see: Roy et al. (2001 ).

Experimental

Crystal data

C₂₂H₄₂N₆·2CH₄O
M_r = 454.70
Monoclinic, P 2₁ /n
a = 11.8705 (16) Å
b = 8.4448 (11) Å
c = 13.4942 (18) Å
β = 94.097 (2)°
V = 1349.3 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 173 K
0.34 × 0.30 × 0.27 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.976, T_max = 0.981
10793 measured reflections
2940 independent reflections
2562 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.113
S = 1.05
2940 reflections
154 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1ⁱ	0.84	2.02	2.8343 (12)	162
Symmetry code: (i) x, y+1, z.

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810013073/sj2765sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810013073/sj2765Isup2.hkl

checkCIF report

Comment top

In past decades, macrocycles with pendant coordinating groups (Madeyski et al., 1984; Hay et al., 1987) have attracted a great deal of attention and have been studied extensively (Melson, 1979) due to the fact that their structures and properties differ markedly from those of the unsubstituted parent molecules. Recently, we have synthesized the title complex, 1,8-bis(2-Cyanoethyl)-5,5,7,12,12,14-hexamethyl-1,4,8,11-tetra- azacyclotetradecane and its structure is reported here.

The title compound, C₂₂H₄₂N₆.2CH₃OH, Fig. 1, comprises a centrosymmetric 14-membered tetra-azacyclotetradecane macrocycle with C9···C11, N3 cyanoethyl substituents on the N2 atoms and two methanol solvate molecules. These substituents are both oriented so the cyano groups lie over opposite faces of the central cavity of the macrocycle. This contrasts sharply with the situation in the structure of 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-tetraaza- cyclotetradecane (Roy et al., 2001), in which the cyanoethyl arms are directed away from the central cavity of the macrocycle. The methanol solvate molecules lie away from the cavity of the macrocycle and are linked to the macrocycles via O1—H1···N1 hydrogen bonds.

Related literature top

For background to macrocycles with pendant coordinating groups, see: Madeyski et al. (1984); Hay et al. (1987); Melson (1979). For a related structure, see: Roy et al. (2001).

Experimental top

An acrylonitrile solution of C-meso-5,5,7,12,12,14-hexamethyl- 1,4,8,11-tetraazacyclotetradecane was heated to reflux for 6 h-10 h, The reaction mixture was cooled to room temperature and colorless crystals of the title compound were obtained by slow evaporation of the solvent at room temperature.

Structure description top

For background to macrocycles with pendant coordinating groups, see: Madeyski et al. (1984); Hay et al. (1987); Melson (1979). For a related structure, see: Roy et al. (2001).

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The structure of the title compound, showing the atom-numbering scheme. Non-H atoms are shown with 30% probability displacement ellipsoids (H atoms are omitted for clarity). [Symmetry code: (i) 1-x, -y, 2-z.]

3,3'-(5,5,7,12,12,14-Hexamethyl-1,4,8,11-tetraazacyclotetradecane- 1,8-diyl)dipropanonitrile methanol disolvate top

Crystal data top

C₂₂H₄₂N₆·2CH₄O	F(000) = 504
M_r = 454.70	D_x = 1.119 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7044 reflections
a = 11.8705 (16) Å	θ = 2.2–27.0°
b = 8.4448 (11) Å	µ = 0.07 mm⁻¹
c = 13.4942 (18) Å	T = 173 K
β = 94.097 (2)°	Block, colourless
V = 1349.3 (3) Å³	0.34 × 0.30 × 0.27 mm
Z = 2

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	2940 independent reflections
Radiation source: fine-focus sealed tube	2562 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
φ and ω scans	θ_max = 27.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −15→15
T_min = 0.976, T_max = 0.981	k = −10→10
10793 measured reflections	l = −17→16

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0618P)² + 0.3251P] where P = (F_o² + 2F_c²)/3
2940 reflections	(Δ/σ)_max = 0.001
154 parameters	Δρ_max = 0.33 e Å⁻³
1 restraint	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₂₂H₄₂N₆·2CH₄O	V = 1349.3 (3) Å³
M_r = 454.70	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.8705 (16) Å	µ = 0.07 mm⁻¹
b = 8.4448 (11) Å	T = 173 K
c = 13.4942 (18) Å	0.34 × 0.30 × 0.27 mm
β = 94.097 (2)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	2940 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	2562 reflections with I > 2σ(I)
T_min = 0.976, T_max = 0.981	R_int = 0.019
10793 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	1 restraint
wR(F²) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.33 e Å⁻³
2940 reflections	Δρ_min = −0.16 e Å⁻³
154 parameters

Special details top

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

	x	y	z	U_iso*/U_eq
C1	0.37856 (9)	0.07773 (12)	0.85259 (8)	0.0257 (2)
H1A	0.3428	0.1592	0.8079	0.031*
H1B	0.4073	0.1303	0.9149	0.031*
C2	0.56583 (9)	0.10757 (12)	0.77704 (7)	0.0245 (2)
C3	0.64934 (10)	−0.00010 (15)	0.72852 (9)	0.0338 (3)
H3A	0.6763	−0.0821	0.7758	0.051*
H3B	0.7135	0.0628	0.7090	0.051*
H3C	0.6118	−0.0501	0.6695	0.051*
C4	0.51883 (10)	0.22792 (14)	0.69961 (8)	0.0314 (3)
H4A	0.4756	0.1722	0.6457	0.047*
H4B	0.5815	0.2855	0.6726	0.047*
H4C	0.4694	0.3029	0.7310	0.047*
C5	0.62179 (8)	0.20068 (12)	0.86592 (7)	0.0239 (2)
H5A	0.6724	0.2813	0.8397	0.029*
H5B	0.5618	0.2580	0.8985	0.029*
C6	0.69062 (8)	0.10371 (12)	0.94599 (7)	0.0233 (2)
H6	0.6658	−0.0091	0.9388	0.028*
C7	0.81748 (9)	0.10933 (15)	0.92898 (9)	0.0332 (3)
H7A	0.8448	0.2184	0.9366	0.050*
H7B	0.8292	0.0719	0.8618	0.050*
H7C	0.8591	0.0413	0.9777	0.050*
C8	0.70816 (8)	0.04726 (12)	1.12482 (8)	0.0251 (2)
H8A	0.7295	0.1080	1.1860	0.030*
H8B	0.7769	−0.0056	1.1036	0.030*
C9	0.69768 (9)	0.32159 (12)	1.06682 (8)	0.0262 (2)
H9A	0.6917	0.3826	1.0040	0.031*
H9B	0.7775	0.3249	1.0937	0.031*
C10	0.62306 (10)	0.39889 (13)	1.14129 (8)	0.0315 (3)
H10A	0.6390	0.3497	1.2074	0.038*
H10B	0.6418	0.5129	1.1472	0.038*
C11	0.50273 (10)	0.38124 (13)	1.11086 (9)	0.0319 (3)
C12	0.38124 (11)	0.83164 (16)	0.55435 (9)	0.0392 (3)
H12A	0.4093	0.9349	0.5339	0.059*
H12B	0.3183	0.7985	0.5081	0.059*
H12C	0.4421	0.7533	0.5540	0.059*
N1	0.47262 (7)	0.00296 (10)	0.80496 (6)	0.0234 (2)
N2	0.66485 (7)	0.15706 (10)	1.04640 (6)	0.0220 (2)
N3	0.40915 (9)	0.36369 (13)	1.08811 (9)	0.0448 (3)
O1	0.34397 (8)	0.84346 (12)	0.65056 (6)	0.0406 (2)
H1	0.3937	0.8886	0.6879	0.061*
H1C	0.5001 (11)	−0.0715 (17)	0.8475 (10)	0.031 (3)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0268 (5)	0.0226 (5)	0.0283 (5)	0.0009 (4)	0.0057 (4)	0.0009 (4)
C2	0.0254 (5)	0.0252 (5)	0.0231 (5)	−0.0026 (4)	0.0042 (4)	−0.0005 (4)
C3	0.0313 (6)	0.0390 (6)	0.0322 (6)	−0.0007 (5)	0.0093 (4)	−0.0079 (5)
C4	0.0346 (6)	0.0346 (6)	0.0248 (5)	−0.0056 (5)	0.0010 (4)	0.0050 (4)
C5	0.0241 (5)	0.0223 (5)	0.0253 (5)	−0.0023 (4)	0.0023 (4)	0.0009 (4)
C6	0.0216 (5)	0.0227 (5)	0.0259 (5)	−0.0008 (4)	0.0037 (4)	−0.0002 (4)
C7	0.0230 (5)	0.0410 (6)	0.0361 (6)	0.0027 (5)	0.0066 (4)	0.0052 (5)
C8	0.0218 (5)	0.0265 (5)	0.0268 (5)	0.0002 (4)	0.0011 (4)	0.0034 (4)
C9	0.0249 (5)	0.0229 (5)	0.0303 (5)	−0.0041 (4)	−0.0013 (4)	−0.0010 (4)
C10	0.0362 (6)	0.0258 (5)	0.0320 (6)	−0.0002 (4)	−0.0014 (4)	−0.0054 (4)
C11	0.0360 (6)	0.0233 (5)	0.0368 (6)	0.0056 (4)	0.0052 (5)	−0.0005 (4)
C12	0.0402 (7)	0.0443 (7)	0.0336 (6)	−0.0018 (5)	0.0048 (5)	−0.0082 (5)
N1	0.0236 (4)	0.0212 (4)	0.0258 (4)	−0.0011 (3)	0.0035 (3)	−0.0004 (3)
N2	0.0217 (4)	0.0205 (4)	0.0236 (4)	−0.0014 (3)	0.0008 (3)	0.0003 (3)
N3	0.0354 (6)	0.0390 (6)	0.0600 (7)	0.0072 (5)	0.0042 (5)	0.0027 (5)
O1	0.0404 (5)	0.0522 (6)	0.0294 (4)	−0.0142 (4)	0.0035 (4)	−0.0044 (4)

Geometric parameters (Å, º) top

C1—N1	1.4701 (13)	C7—H7B	0.9800
C1—C8ⁱ	1.5204 (14)	C7—H7C	0.9800
C1—H1A	0.9900	C8—N2	1.4717 (13)
C1—H1B	0.9900	C8—C1ⁱ	1.5204 (14)
C2—N1	1.4853 (13)	C8—H8A	0.9900
C2—C3	1.5267 (15)	C8—H8B	0.9900
C2—C4	1.5338 (15)	C9—N2	1.4639 (13)
C2—C5	1.5441 (14)	C9—C10	1.5322 (16)
C3—H3A	0.9800	C9—H9A	0.9900
C3—H3B	0.9800	C9—H9B	0.9900
C3—H3C	0.9800	C10—C11	1.4655 (16)
C4—H4A	0.9800	C10—H10A	0.9900
C4—H4B	0.9800	C10—H10B	0.9900
C4—H4C	0.9800	C11—N3	1.1408 (16)
C5—C6	1.5426 (14)	C12—O1	1.4048 (15)
C5—H5A	0.9900	C12—H12A	0.9800
C5—H5B	0.9900	C12—H12B	0.9800
C6—N2	1.4804 (13)	C12—H12C	0.9800
C6—C7	1.5401 (14)	N1—H1C	0.897 (14)
C6—H6	1.0000	O1—H1	0.8400
C7—H7A	0.9800

N1—C1—C8ⁱ	109.62 (8)	C6—C7—H7B	109.5
N1—C1—H1A	109.7	H7A—C7—H7B	109.5
C8ⁱ—C1—H1A	109.7	C6—C7—H7C	109.5
N1—C1—H1B	109.7	H7A—C7—H7C	109.5
C8ⁱ—C1—H1B	109.7	H7B—C7—H7C	109.5
H1A—C1—H1B	108.2	N2—C8—C1ⁱ	112.02 (8)
N1—C2—C3	105.83 (9)	N2—C8—H8A	109.2
N1—C2—C4	109.01 (8)	C1ⁱ—C8—H8A	109.2
C3—C2—C4	108.56 (9)	N2—C8—H8B	109.2
N1—C2—C5	113.12 (8)	C1ⁱ—C8—H8B	109.2
C3—C2—C5	112.33 (9)	H8A—C8—H8B	107.9
C4—C2—C5	107.88 (8)	N2—C9—C10	111.67 (9)
C2—C3—H3A	109.5	N2—C9—H9A	109.3
C2—C3—H3B	109.5	C10—C9—H9A	109.3
H3A—C3—H3B	109.5	N2—C9—H9B	109.3
C2—C3—H3C	109.5	C10—C9—H9B	109.3
H3A—C3—H3C	109.5	H9A—C9—H9B	107.9
H3B—C3—H3C	109.5	C11—C10—C9	111.75 (9)
C2—C4—H4A	109.5	C11—C10—H10A	109.3
C2—C4—H4B	109.5	C9—C10—H10A	109.3
H4A—C4—H4B	109.5	C11—C10—H10B	109.3
C2—C4—H4C	109.5	C9—C10—H10B	109.3
H4A—C4—H4C	109.5	H10A—C10—H10B	107.9
H4B—C4—H4C	109.5	N3—C11—C10	178.26 (13)
C6—C5—C2	116.79 (8)	O1—C12—H12A	109.5
C6—C5—H5A	108.1	O1—C12—H12B	109.5
C2—C5—H5A	108.1	H12A—C12—H12B	109.5
C6—C5—H5B	108.1	O1—C12—H12C	109.5
C2—C5—H5B	108.1	H12A—C12—H12C	109.5
H5A—C5—H5B	107.3	H12B—C12—H12C	109.5
N2—C6—C7	113.28 (8)	C1—N1—C2	117.27 (8)
N2—C6—C5	110.23 (8)	C1—N1—H1C	105.9 (9)
C7—C6—C5	110.72 (8)	C2—N1—H1C	109.6 (9)
N2—C6—H6	107.4	C9—N2—C8	112.83 (8)
C7—C6—H6	107.4	C9—N2—C6	113.05 (8)
C5—C6—H6	107.4	C8—N2—C6	112.45 (8)
C6—C7—H7A	109.5	C12—O1—H1	109.5

N1—C2—C5—C6	68.30 (11)	C5—C2—N1—C1	57.41 (12)
C3—C2—C5—C6	−51.44 (12)	C10—C9—N2—C8	−79.38 (11)
C4—C2—C5—C6	−171.05 (8)	C10—C9—N2—C6	151.61 (9)
C2—C5—C6—N2	−136.19 (9)	C1ⁱ—C8—N2—C9	139.60 (9)
C2—C5—C6—C7	97.66 (11)	C1ⁱ—C8—N2—C6	−91.08 (10)
N2—C9—C10—C11	−52.36 (12)	C7—C6—N2—C9	61.30 (11)
C9—C10—C11—N3	80 (4)	C5—C6—N2—C9	−63.39 (10)
C8ⁱ—C1—N1—C2	179.81 (8)	C7—C6—N2—C8	−67.90 (11)
C3—C2—N1—C1	−179.19 (9)	C5—C6—N2—C8	167.41 (8)
C4—C2—N1—C1	−62.60 (11)

Symmetry code: (i) −x+1, −y, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1ⁱⁱ	0.84	2.02	2.8343 (12)	162

Symmetry code: (ii) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₂₂H₄₂N₆·2CH₄O
M_r	454.70
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	173
a, b, c (Å)	11.8705 (16), 8.4448 (11), 13.4942 (18)
β (°)	94.097 (2)
V (Å³)	1349.3 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.34 × 0.30 × 0.27

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.976, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	10793, 2940, 2562
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.640

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.113, 1.05
No. of reflections	2940
No. of parameters	154
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.16

Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1ⁱ	0.84	2.02	2.8343 (12)	162.2

Symmetry code: (i) x, y+1, z.

Acknowledgements

The authors acknowledge Pingdingshan University for supporting this work.

References

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Volume 66| Part 5| May 2010| Page o1089

https://doi.org/10.1107/S1600536810013073

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

3,3′-(5,5,7,12,12,14-Hexa­methyl-1,4,8,11-tetra­aza­cyclo­tetra­decane-1,8-diyl)di­propano­nitrile methanol disolvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

3,3′-(5,5,7,12,12,14-Hexamethyl-1,4,8,11-tetraazacyclotetradecane-1,8-diyl)dipropanonitrile methanol disolvate