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Molecules of 1,4,8,11-tetra­aza­cyclo­tetra­decane-5,7-dione, or cis-dioxocyclam, C10H20N4O2, lie across mirror planes in space group Cmca; the crystal structure reveals interleaved columns of cis-dioxocyclam mol­ecules along the 21 screw axis parallel to the crystallographic b axis. The columns are interconnected in a chain-like arrangement by an amido hydrogen-bonding network (N...O = 2.816 Å) and an amino hydrogen-bonding network (N...N = 3.193 Å). The intracolumn spacing is 9.02 Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270102003165/bk1641sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270102003165/bk1641Isup2.hkl
Contains datablock I

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S0108270102003165/bk1641sup3.pdf
Supplementary material

CCDC reference: 184495

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Bruker, 2001).

1,4,8,11-Tetraazacyclotetradecane-5,7-dione top
Crystal data top
C10H20N4O2F(000) = 992
Mr = 228.30Dx = 1.28 Mg m3
Dm = 1.23 Mg m3
Dm measured by picnometry
Orthorhombic, CmcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2bc 2Cell parameters from 7156 reflections
a = 15.1714 (9) Åθ = 2.4–28.3°
b = 9.0190 (5) ŵ = 0.09 mm1
c = 17.2111 (10) ÅT = 100 K
V = 2355.0 (2) Å3Block, colourless
Z = 80.45 × 0.37 × 0.32 mm
Data collection top
SMART APEX CCD area-detector
diffractometer
1455 independent reflections
Radiation source: normal-focus sealed tube1359 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.017
ω scansθmax = 28.3°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)
h = 2019
Tmin = 0.96, Tmax = 0.97k = 1111
9566 measured reflectionsl = 2221
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)] = 0.034Hydrogen site location: difference Fourier map
wR(F2) = 0.088H atoms treated by a mixture of independent and constrained refinement
S = 1.08 w = 1/[σ2(Fo2) + (0.044P)2 + 1.24P]
where P = (Fo2 + Fc2)/3
1455 reflections(Δ/σ)max = 0.013
98 parametersΔρmax = 0.36 e Å3
0 restraintsΔρmin = 0.14 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*/UeqOcc. (<1)
O10.10535 (5)0.21627 (7)0.30402 (4)0.0237 (2)
N10.09778 (5)0.63132 (8)0.43791 (5)0.0203 (2)
H1NA0.0942 (13)0.564 (2)0.4674 (12)0.013 (5)*0.50
H1NB0.0534 (14)0.605 (2)0.4122 (12)0.013 (5)*0.50
N20.11837 (5)0.46558 (8)0.29273 (4)0.0188 (2)
H2NA0.1043 (8)0.5433 (14)0.2655 (7)0.029 (3)*
C10.17912 (5)0.62745 (10)0.39300 (5)0.0204 (2)
H1A0.23000.64060.42840.029 (3)*
H1B0.17930.71060.35540.024 (3)*
C20.18899 (5)0.48208 (10)0.34940 (5)0.0209 (2)
H2A0.24670.47990.32250.028 (3)*
H2B0.18720.39850.38660.026 (3)*
C30.08071 (6)0.33573 (9)0.27639 (5)0.0181 (2)
C40.00000.34517 (13)0.22393 (7)0.0198 (3)
H4A0.00000.26250.18610.029 (4)*
H4B0.00000.43990.19490.023 (4)*
C50.08458 (6)0.77339 (9)0.47752 (5)0.0207 (2)
H5A0.08250.85390.43840.022 (3)*
H5B0.13520.79260.51240.027 (3)*
C60.00000.77510 (14)0.52476 (7)0.0230 (3)
H6A0.00000.68780.55960.027 (4)*
H6B0.00000.86480.55790.035 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0351 (4)0.0139 (3)0.0221 (3)0.0037 (2)0.0003 (3)0.0006 (2)
N10.0178 (4)0.0166 (4)0.0265 (4)0.0029 (3)0.0017 (3)0.0031 (3)
N20.0207 (4)0.0141 (4)0.0217 (4)0.0018 (3)0.0012 (3)0.0024 (3)
C10.0150 (4)0.0203 (4)0.0259 (4)0.0032 (3)0.0019 (3)0.0022 (3)
C20.0153 (4)0.0208 (4)0.0265 (4)0.0023 (3)0.0020 (3)0.0025 (3)
C30.0248 (4)0.0155 (4)0.0142 (4)0.0024 (3)0.0061 (3)0.0012 (3)
C40.0318 (7)0.0142 (5)0.0134 (5)0.0000.0000.0019 (4)
C50.0242 (4)0.0171 (4)0.0209 (4)0.0027 (3)0.0059 (3)0.0025 (3)
C60.0340 (7)0.0193 (6)0.0156 (5)0.0000.0000.0044 (4)
Geometric parameters (Å, º) top
O1—C31.236 (1)C2—H2A0.99
N1—C11.457 (1)C2—H2B0.99
N1—C51.465 (1)C3—C41.524 (1)
N1—H1NA0.80 (2)C4—H4A0.99
N1—H1NB0.84 (2)C4—H4B0.99
N2—C31.333 (1)C5—C61.519 (1)
N2—C21.456 (1)C5—H5A0.99
N2—H2NA0.87 (1)C5—H5B0.99
C1—C21.518 (2)C6—H6A0.99
C1—H1A0.99C6—H6B0.99
C1—H1B0.99
C1—N1—C5112.56 (7)C1—C2—H2B109.6
C1—N1—H1NA112.2 (15)H2A—C2—H2B108.1
C5—N1—H1NA111.5 (15)O1—C3—N2123.72 (8)
C1—N1—H1NB113.1 (13)O1—C3—C4121.33 (8)
C5—N1—H1NB112.5 (14)N2—C3—C4114.86 (8)
H1NA—N1—H1NB93.6 (19)C3—C4—H4A110.3
C3—N2—C2123.12 (7)C3—C4—H4B110.3
C3—N2—H2NA119.3 (8)H4A—C4—H4B108.6
C2—N2—H2NA117.3 (8)N1—C5—C6111.92 (8)
N1—C1—C2111.50 (7)N1—C5—H5A109.2
N1—C1—H1A109.3C6—C5—H5A109.2
C2—C1—H1A109.3N1—C5—H5B109.2
N1—C1—H1B109.3C6—C5—H5B109.2
C2—C1—H1B109.3H5A—C5—H5B107.9
H1A—C1—H1B108.0C5—C6—H6A108.5
N2—C2—C1110.29 (7)C5—C6—H6B108.5
N2—C2—H2A109.6H6A—C6—H6B107.5
C1—C2—H2A109.6C3—C4—C3i106.95 (9)
N2—C2—H2B109.6C5—C6—C5i115.27 (9)
Symmetry code: (i) x+1/2, y+1, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1NA···N1ii0.80 (2)2.40 (2)3.190 (1)173.9 (15)
N1—H1NB···N1iii0.84 (2)2.35 (2)2.967 (1)131.0 (14)
N2—H2NA···O1iv0.87 (1)1.97 (2)2.815 (1)164.9 (13)
Symmetry codes: (ii) x, y+1, z+1; (iii) x, y, z; (iv) x, y+1/2, z+1/2.
 

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