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The title compound, C40H40N4O4, contains a 1,4,8,11-tetra­aza­cyclo­tetra­decane ring, with four benzyl and two methyl­ene substituents and also four carbonyl groups. This mol­ecule is only the second reported structure of the 1,4,8,11-tetra­aza­cyclo­tetra­decane ring with four carbonyl groups on C atoms 2, 3, 9 and 10. Large-ring nitro­gen heterocycles are often useful for their ability to selectively coordinate with certain metal ions, and are also sometimes used as precursors to new energetic materials. In the crystal structure the molecule is centrosymmetric.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803014843/lh6076sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803014843/lh6076Isup2.hkl
Contains datablock I

CCDC reference: 221681

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.048
  • wR factor = 0.139
  • Data-to-parameter ratio = 13.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
REFLT_03 From the CIF: _diffrn_reflns_theta_max 67.21 From the CIF: _reflns_number_total 2938 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 3124 Completeness (_total/calc) 94.05% Alert C: < 95% complete PLAT_369 Alert C Long C(sp2)-C(sp2) Bond C2 - C3 = 1.53 Ang. General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 67.21 From the CIF: _reflns_number_total 2938 From the CIF: _diffrn_reflns_limit_ max hkl 11. 9. 20. From the CIF: _diffrn_reflns_limit_ min hkl -11. -11. -20. TEST1: Expected hkl limits for theta max Calculated maximum hkl 11. 11. 22. Calculated minimum hkl -11. -11. -22. ALERT: Expected hkl max differ from CIF values
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
2 Alert Level C = Please check

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SHELXTL (Sheldrick, 1997); program(s) used to solve structure: SHELXTL; program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

1,4,8,11-Tetrabenzyl-6,13-dimethylene-1,4,8,11-tetraazacyclotetradecane- 2,3,9,10-tetraone top
Crystal data top
C40H40N4O4F(000) = 680
Mr = 640.76Dx = 1.221 Mg m3
Monoclinic, P21/cMelting point: 284 K
Hall symbol: -P 2ybcCu Kα radiation, λ = 1.54178 Å
a = 9.9969 (3) ÅCell parameters from 3915 reflections
b = 9.3366 (3) Åθ = 4.4–60.6°
c = 18.6720 (6) ŵ = 0.64 mm1
β = 90.758 (2)°T = 295 K
V = 1742.64 (9) Å3Thin plate, colorless
Z = 20.18 × 0.16 × 0.03 mm
Data collection top
Bruker SMART-CCD
diffractometer
2938 independent reflections
Radiation source: fine-focus sealed tube1764 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.096
ω scansθmax = 67.2°, θmin = 4.4°
Absorption correction: integration
(Wuensch & Prewitt, 1965)
h = 1111
Tmin = 0.897, Tmax = 0.981k = 119
10138 measured reflectionsl = 2020
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)] = 0.048H-atom parameters constrained
wR(F2) = 0.139 w = 1/[σ2(Fo2) + (0.0773P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.91(Δ/σ)max < 0.001
2938 reflectionsΔρmax = 0.15 e Å3
218 parametersΔρmin = 0.15 e Å3
0 restraintsExtinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0048 (7)
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
N10.43480 (18)0.57576 (16)0.37534 (8)0.0671 (5)
C10.4346 (2)0.4562 (2)0.32461 (10)0.0699 (6)
H1A0.36050.39290.33520.084*
H1B0.51680.40210.33060.084*
C110.4222 (2)0.50611 (19)0.24751 (10)0.0680 (5)
C120.3032 (3)0.5540 (3)0.22025 (13)0.1025 (8)
H12A0.22810.55520.24910.123*
C130.2927 (3)0.6010 (4)0.14983 (16)0.1212 (10)
H13A0.21100.63400.13210.145*
C140.4004 (4)0.5990 (3)0.10686 (14)0.1005 (8)
H14A0.39300.62870.05940.121*
C150.5189 (3)0.5533 (3)0.13369 (13)0.0946 (8)
H15A0.59410.55380.10490.114*
C160.5296 (3)0.5057 (2)0.20349 (12)0.0815 (6)
H16A0.61170.47280.22080.098*
C20.3407 (2)0.5960 (2)0.42418 (12)0.0716 (6)
O20.34354 (17)0.69188 (17)0.46907 (9)0.0979 (5)
C30.2166 (2)0.5004 (2)0.42217 (11)0.0736 (6)
O30.11917 (16)0.53828 (17)0.38595 (9)0.0941 (5)
N40.21932 (17)0.38257 (19)0.46380 (8)0.0730 (5)
C40.0989 (2)0.2916 (3)0.46770 (11)0.0853 (7)
H4A0.02010.35040.45950.102*
H4B0.09310.25130.51550.102*
C410.0996 (2)0.1717 (2)0.41389 (11)0.0740 (6)
C420.1216 (3)0.0308 (3)0.43390 (16)0.1037 (8)
H42A0.13920.00790.48160.124*
C430.1170 (3)0.0788 (3)0.3811 (2)0.1207 (11)
H43A0.13070.17410.39380.145*
C440.0921 (3)0.0422 (4)0.3116 (2)0.1213 (10)
H44A0.08950.11380.27700.146*
C450.0716 (3)0.0930 (4)0.29184 (16)0.1091 (9)
H45A0.05460.11500.24400.131*
C460.0755 (2)0.1994 (3)0.34209 (12)0.0867 (7)
H46A0.06140.29350.32750.104*
C50.3372 (2)0.3398 (2)0.50508 (10)0.0706 (6)
H5A0.41530.38430.48430.085*
H5B0.34800.23690.50100.085*
C60.3325 (2)0.3789 (3)0.58343 (11)0.0783 (6)
C6A0.2368 (3)0.4524 (4)0.61191 (15)0.1319 (12)
H6AA0.23990.47410.66050.172*
H6AB0.16510.48340.58370.172*
C70.4506 (2)0.3262 (2)0.62656 (11)0.0818 (7)
H7A0.42390.31330.67590.098*
H7B0.47790.23360.60830.098*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0690 (12)0.0625 (9)0.0696 (10)0.0066 (8)0.0103 (9)0.0018 (7)
C10.0723 (15)0.0644 (11)0.0729 (12)0.0017 (9)0.0029 (10)0.0052 (9)
C110.0692 (15)0.0634 (11)0.0712 (12)0.0034 (10)0.0053 (11)0.0010 (9)
C120.0785 (18)0.149 (2)0.0801 (15)0.0167 (16)0.0056 (13)0.0159 (14)
C130.101 (2)0.168 (3)0.0947 (19)0.027 (2)0.0203 (18)0.0248 (18)
C140.123 (3)0.1004 (18)0.0778 (15)0.0090 (16)0.0046 (17)0.0174 (12)
C150.101 (2)0.0948 (16)0.0887 (17)0.0179 (14)0.0166 (15)0.0054 (13)
C160.0814 (17)0.0831 (14)0.0798 (14)0.0038 (12)0.0017 (12)0.0009 (11)
C20.0701 (15)0.0692 (12)0.0750 (13)0.0049 (10)0.0169 (11)0.0049 (10)
O20.1027 (13)0.0892 (10)0.1012 (11)0.0022 (9)0.0141 (9)0.0309 (9)
C30.0681 (15)0.0809 (14)0.0715 (12)0.0074 (11)0.0078 (10)0.0152 (11)
O30.0702 (11)0.1008 (11)0.1105 (11)0.0114 (8)0.0259 (9)0.0032 (9)
N40.0608 (11)0.0905 (12)0.0676 (10)0.0069 (9)0.0060 (8)0.0020 (9)
C40.0648 (15)0.1153 (17)0.0758 (13)0.0159 (13)0.0012 (11)0.0012 (12)
C410.0538 (13)0.0864 (14)0.0817 (13)0.0106 (10)0.0036 (10)0.0083 (11)
C420.0755 (18)0.114 (2)0.122 (2)0.0129 (15)0.0022 (15)0.0334 (17)
C430.088 (2)0.0759 (17)0.198 (4)0.0028 (14)0.011 (2)0.006 (2)
C440.094 (2)0.117 (3)0.153 (3)0.0125 (18)0.000 (2)0.034 (2)
C450.106 (2)0.118 (2)0.1024 (18)0.0018 (17)0.0093 (16)0.0230 (17)
C460.0836 (17)0.0946 (15)0.0817 (15)0.0022 (12)0.0109 (12)0.0050 (12)
C50.0641 (14)0.0818 (13)0.0657 (12)0.0034 (10)0.0034 (10)0.0008 (9)
C60.0681 (15)0.1042 (16)0.0625 (12)0.0161 (13)0.0021 (11)0.0026 (11)
C6A0.082 (2)0.232 (4)0.0810 (16)0.009 (2)0.0021 (14)0.045 (2)
C70.0910 (17)0.0835 (14)0.0705 (12)0.0232 (12)0.0126 (11)0.0142 (10)
Geometric parameters (Å, º) top
N1—C21.332 (3)C4—H4A0.9700
N1—C11.464 (2)C4—H4B0.9700
N1—C7i1.467 (3)C41—C461.384 (3)
C1—C111.517 (3)C41—C421.384 (3)
C1—H1A0.9700C42—C431.421 (4)
C1—H1B0.9700C42—H42A0.9300
C11—C161.360 (3)C43—C441.362 (4)
C11—C121.364 (3)C43—H43A0.9300
C12—C131.389 (4)C44—C451.331 (4)
C12—H12A0.9300C44—H44A0.9300
C13—C141.351 (4)C45—C461.367 (3)
C13—H13A0.9300C45—H45A0.9300
C14—C151.349 (4)C46—H46A0.9300
C14—H14A0.9300C5—C61.509 (3)
C15—C161.380 (3)C5—H5A0.9700
C15—H15A0.9300C5—H5B0.9700
C16—H16A0.9300C6—C6A1.297 (4)
C2—O21.227 (2)C6—C71.504 (3)
C2—C31.529 (3)C6A—H6AA0.9300
C3—O31.230 (2)C6A—H6AB0.9300
C3—N41.347 (3)C7—N1i1.467 (3)
N4—C51.455 (2)C7—H7A0.9700
N4—C41.476 (3)C7—H7B0.9700
C4—C411.504 (3)
C2—N1—C1123.77 (17)N4—C4—H4B109.1
C2—N1—C7i119.12 (17)C41—C4—H4B109.1
C1—N1—C7i117.05 (18)H4A—C4—H4B107.8
N1—C1—C11112.30 (15)C46—C41—C42117.7 (2)
N1—C1—H1A109.1C46—C41—C4120.4 (2)
C11—C1—H1A109.1C42—C41—C4121.9 (2)
N1—C1—H1B109.1C41—C42—C43119.6 (3)
C11—C1—H1B109.1C41—C42—H42A120.2
H1A—C1—H1B107.9C43—C42—H42A120.2
C16—C11—C12117.8 (2)C44—C43—C42119.0 (3)
C16—C11—C1121.20 (19)C44—C43—H43A120.5
C12—C11—C1121.0 (2)C42—C43—H43A120.5
C11—C12—C13120.8 (3)C45—C44—C43121.9 (3)
C11—C12—H12A119.6C45—C44—H44A119.1
C13—C12—H12A119.6C43—C44—H44A119.1
C14—C13—C12120.5 (3)C44—C45—C46119.8 (3)
C14—C13—H13A119.8C44—C45—H45A120.1
C12—C13—H13A119.8C46—C45—H45A120.1
C15—C14—C13119.1 (2)C45—C46—C41122.2 (2)
C15—C14—H14A120.4C45—C46—H46A118.9
C13—C14—H14A120.4C41—C46—H46A118.9
C14—C15—C16120.6 (3)N4—C5—C6114.31 (18)
C14—C15—H15A119.7N4—C5—H5A108.7
C16—C15—H15A119.7C6—C5—H5A108.7
C11—C16—C15121.2 (2)N4—C5—H5B108.7
C11—C16—H16A119.4C6—C5—H5B108.7
C15—C16—H16A119.4H5A—C5—H5B107.6
O2—C2—N1124.1 (2)C6A—C6—C7122.1 (2)
O2—C2—C3117.0 (2)C6A—C6—C5123.9 (2)
N1—C2—C3118.73 (17)C7—C6—C5113.9 (2)
O3—C3—N4124.2 (2)C6—C6A—H6AA120.0
O3—C3—C2118.8 (2)C6—C6A—H6AB120.0
N4—C3—C2116.89 (18)H6AA—C6A—H6AB120.0
C3—N4—C5122.67 (18)N1i—C7—C6113.02 (16)
C3—N4—C4119.22 (18)N1i—C7—H7A109.0
C5—N4—C4118.11 (17)C6—C7—H7A109.0
N4—C4—C41112.57 (18)N1i—C7—H7B109.0
N4—C4—H4A109.1C6—C7—H7B109.0
C41—C4—H4A109.1H7A—C7—H7B107.8
C6i—C7i—N1—C293.3 (2)C3—N4—C5—C6100.4 (2)
C7i—N1—C2—C3175.43 (17)N4—C5—C6—C7176.35 (17)
N1—C2—C3—N493.9 (2)C5—C6—C7—N1i85.5 (2)
C2—C3—N4—C54.6 (3)O2—C2—C3—O386.9 (2)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C14—H14A···O2ii0.932.423.274 (3)152
Symmetry code: (ii) x, y+3/2, z1/2.
 

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