In the title compound, C10H18N2O4, the diazacyclohexane ring is in a normal chair conformation. The molecule packs to form hydrogen-bonded dimers around a center of symmetry.
Supporting information
CCDC reference: 177211
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.004 Å
- R factor = 0.066
- wR factor = 0.135
- Data-to-parameter ratio = 13.2
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level A:
EXPT_108 Alert A The magnitudes of the crystal dimensions do not
match the min, mid and max definitions
DIFF_020 Alert A _diffrn_standards_interval_count and
_diffrn_standards_interval_time are missing. Number of measurements
between standards or time (min) between standards.
DIFF_022 Alert A _diffrn_standards_decay_% is missing
Percentage decrease in standards intensity.
Alert Level B:
CRYSS_01 Alert B The magnitudes of the crystal dimensions do not
match the min, mid and max definitions
3 Alert Level A = Potentially serious problem
1 Alert Level B = Potential problem
0 Alert Level C = Please check
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001).
Crystal data top
C10H18N2O4 | F(000) = 992 |
Mr = 230.26 | Dx = 1.365 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 24.2121 (16) Å | Cell parameters from 3629 reflections |
b = 5.3063 (4) Å | θ = 2.7–28.1° |
c = 19.7644 (12) Å | µ = 0.11 mm−1 |
β = 118.023 (1)° | T = 294 K |
V = 2241.6 (3) Å3 | Thick plate, colorless |
Z = 8 | 0.11 × 0.35 × 0.40 mm |
Data collection top
Bruker SMART 1000 diffractometer | 2044 independent reflections |
Radiation source: fine-focus sealed tube | 1621 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.041 |
φ and ω scans | θmax = 25.3°, θmin = 1.9° |
Absorption correction: integration (Bruker, 2001) | h = −28→29 |
Tmin = 0.961, Tmax = 0.984 | k = −6→6 |
6438 measured reflections | l = −23→23 |
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)] = 0.066 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.135 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.24 | w = 1/[σ2(Fo2) + (0.0406P)2 + 2.4823P] where P = (Fo2 + 2Fc2)/3 |
2044 reflections | (Δ/σ)max = 0.003 |
155 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.18 e Å−3 |
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. Coordinates only refined for hydroxyl H atoms, all others riding. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.11545 (9) | 0.1981 (4) | 0.11352 (11) | 0.0345 (5) | |
C1 | 0.12767 (11) | 0.0227 (5) | 0.07321 (14) | 0.0343 (6) | |
O1 | 0.08695 (9) | −0.0438 (4) | 0.00922 (11) | 0.0561 (6) | |
C1A | 0.19260 (12) | −0.0856 (5) | 0.10688 (14) | 0.0396 (7) | |
H1AA | 0.2223 | 0.0503 | 0.1170 | 0.048* | |
H1AB | 0.2025 | −0.1653 | 0.1554 | 0.048* | |
C1B | 0.20001 (15) | −0.2757 (6) | 0.05528 (17) | 0.0594 (9) | |
H1BA | 0.2425 | −0.3347 | 0.0787 | 0.089* | |
H1BB | 0.1899 | −0.1984 | 0.0069 | 0.089* | |
H1BC | 0.1724 | −0.4152 | 0.0472 | 0.089* | |
C2 | 0.15803 (11) | 0.2790 (5) | 0.19165 (14) | 0.0359 (6) | |
H2A | 0.1983 | 0.1977 | 0.2089 | 0.043* | |
H2B | 0.1642 | 0.4598 | 0.1925 | 0.043* | |
N3 | 0.13260 (9) | 0.2143 (4) | 0.24266 (11) | 0.0327 (5) | |
C3 | 0.15226 (11) | −0.0008 (5) | 0.28538 (13) | 0.0340 (6) | |
O3 | 0.19408 (9) | −0.1287 (4) | 0.28501 (11) | 0.0495 (5) | |
C3A | 0.12253 (12) | −0.0661 (5) | 0.33506 (15) | 0.0411 (7) | |
H3AA | 0.0798 | −0.1200 | 0.3026 | 0.049* | |
H3AB | 0.1211 | 0.0840 | 0.3622 | 0.049* | |
C3B | 0.15687 (14) | −0.2715 (6) | 0.39274 (17) | 0.0523 (8) | |
H3BA | 0.1346 | −0.3110 | 0.4208 | 0.078* | |
H3BB | 0.1983 | −0.2147 | 0.4276 | 0.078* | |
H3BC | 0.1595 | −0.4194 | 0.3664 | 0.078* | |
C4 | 0.07162 (11) | 0.3322 (5) | 0.21959 (14) | 0.0374 (6) | |
H4A | 0.0758 | 0.5142 | 0.2208 | 0.045* | |
H4B | 0.0560 | 0.2843 | 0.2549 | 0.045* | |
C5 | 0.02631 (12) | 0.2463 (5) | 0.13916 (15) | 0.0400 (7) | |
O5A | 0.01854 (10) | −0.0171 (4) | 0.14378 (12) | 0.0497 (6) | |
H5A | −0.0089 (15) | −0.087 (7) | 0.104 (2) | 0.070 (12)* | |
O5B | −0.02987 (9) | 0.3789 (5) | 0.11659 (12) | 0.0548 (6) | |
C6 | 0.05270 (12) | 0.3048 (6) | 0.08438 (15) | 0.0432 (7) | |
H6A | 0.0255 | 0.2345 | 0.0343 | 0.052* | |
H6B | 0.0544 | 0.4858 | 0.0789 | 0.052* | |
H5B | −0.0567 (19) | 0.302 (7) | 0.072 (2) | 0.092 (13)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0278 (11) | 0.0452 (13) | 0.0270 (11) | 0.0008 (10) | 0.0099 (9) | 0.0007 (10) |
C1 | 0.0329 (14) | 0.0412 (16) | 0.0294 (14) | −0.0036 (12) | 0.0150 (12) | 0.0018 (12) |
O1 | 0.0365 (11) | 0.0818 (16) | 0.0365 (11) | 0.0009 (11) | 0.0059 (9) | −0.0196 (11) |
C1A | 0.0333 (15) | 0.0489 (17) | 0.0330 (14) | 0.0007 (13) | 0.0126 (12) | 0.0010 (13) |
C1B | 0.061 (2) | 0.069 (2) | 0.0457 (18) | 0.0226 (18) | 0.0226 (15) | 0.0014 (16) |
C2 | 0.0314 (14) | 0.0408 (16) | 0.0318 (13) | −0.0062 (12) | 0.0118 (11) | −0.0059 (12) |
N3 | 0.0276 (11) | 0.0403 (13) | 0.0285 (11) | 0.0001 (10) | 0.0118 (9) | −0.0050 (10) |
C3 | 0.0281 (13) | 0.0409 (16) | 0.0268 (13) | 0.0000 (12) | 0.0078 (11) | −0.0066 (12) |
O3 | 0.0478 (12) | 0.0546 (13) | 0.0505 (12) | 0.0163 (10) | 0.0268 (10) | 0.0070 (10) |
C3A | 0.0401 (15) | 0.0450 (17) | 0.0372 (15) | −0.0022 (13) | 0.0174 (12) | −0.0046 (13) |
C3B | 0.0571 (19) | 0.053 (2) | 0.0461 (17) | −0.0030 (16) | 0.0239 (15) | 0.0081 (15) |
C4 | 0.0373 (15) | 0.0380 (16) | 0.0350 (14) | 0.0034 (12) | 0.0155 (12) | −0.0045 (12) |
C5 | 0.0319 (14) | 0.0470 (19) | 0.0363 (15) | 0.0075 (13) | 0.0120 (12) | −0.0022 (13) |
O5A | 0.0435 (12) | 0.0511 (14) | 0.0492 (13) | −0.0052 (10) | 0.0173 (11) | −0.0092 (11) |
O5B | 0.0352 (11) | 0.0792 (16) | 0.0426 (12) | 0.0202 (11) | 0.0121 (10) | −0.0069 (11) |
C6 | 0.0341 (14) | 0.0555 (18) | 0.0331 (14) | 0.0069 (13) | 0.0101 (12) | 0.0003 (13) |
Geometric parameters (Å, º) top
N1—C1 | 1.345 (3) | C3—C3A | 1.506 (3) |
N1—C2 | 1.461 (3) | C3A—C3B | 1.513 (4) |
N1—C6 | 1.462 (3) | C3A—H3AA | 0.9700 |
C1—O1 | 1.235 (3) | C3A—H3AB | 0.9700 |
C1—C1A | 1.504 (4) | C3B—H3BA | 0.9600 |
C1A—C1B | 1.504 (4) | C3B—H3BB | 0.9600 |
C1A—H1AA | 0.9700 | C3B—H3BC | 0.9600 |
C1A—H1AB | 0.9700 | C4—C5 | 1.517 (4) |
C1B—H1BA | 0.9600 | C4—H4A | 0.9700 |
C1B—H1BB | 0.9600 | C4—H4B | 0.9700 |
C1B—H1BC | 0.9600 | C5—O5B | 1.405 (3) |
C2—N3 | 1.448 (3) | C5—O5A | 1.419 (3) |
C2—H2A | 0.9700 | C5—C6 | 1.525 (4) |
C2—H2B | 0.9700 | O5A—H5A | 0.84 (3) |
N3—C3 | 1.366 (3) | O5B—H5B | 0.92 (4) |
N3—C4 | 1.465 (3) | C6—H6A | 0.9700 |
C3—O3 | 1.222 (3) | C6—H6B | 0.9700 |
| | | |
C1—N1—C2 | 125.9 (2) | C3—C3A—H3AA | 108.9 |
C1—N1—C6 | 120.8 (2) | C3B—C3A—H3AA | 108.9 |
C2—N1—C6 | 112.9 (2) | C3—C3A—H3AB | 108.9 |
O1—C1—N1 | 120.8 (2) | C3B—C3A—H3AB | 108.9 |
O1—C1—C1A | 120.6 (2) | H3AA—C3A—H3AB | 107.7 |
N1—C1—C1A | 118.5 (2) | C3A—C3B—H3BA | 109.5 |
C1B—C1A—C1 | 112.9 (2) | C3A—C3B—H3BB | 109.5 |
C1B—C1A—H1AA | 109.0 | H3BA—C3B—H3BB | 109.5 |
C1—C1A—H1AA | 109.0 | C3A—C3B—H3BC | 109.5 |
C1B—C1A—H1AB | 109.0 | H3BA—C3B—H3BC | 109.5 |
C1—C1A—H1AB | 109.0 | H3BB—C3B—H3BC | 109.5 |
H1AA—C1A—H1AB | 107.8 | N3—C4—C5 | 108.9 (2) |
C1A—C1B—H1BA | 109.5 | N3—C4—H4A | 109.9 |
C1A—C1B—H1BB | 109.5 | C5—C4—H4A | 109.9 |
H1BA—C1B—H1BB | 109.5 | N3—C4—H4B | 109.9 |
C1A—C1B—H1BC | 109.5 | C5—C4—H4B | 109.9 |
H1BA—C1B—H1BC | 109.5 | H4A—C4—H4B | 108.3 |
H1BB—C1B—H1BC | 109.5 | O5B—C5—O5A | 112.1 (2) |
N3—C2—N1 | 110.28 (19) | O5B—C5—C4 | 107.3 (2) |
N3—C2—H2A | 109.6 | O5A—C5—C4 | 106.3 (2) |
N1—C2—H2A | 109.6 | O5B—C5—C6 | 109.8 (2) |
N3—C2—H2B | 109.6 | O5A—C5—C6 | 111.0 (2) |
N1—C2—H2B | 109.6 | C4—C5—C6 | 110.2 (2) |
H2A—C2—H2B | 108.1 | C5—O5A—H5A | 117 (2) |
C3—N3—C2 | 119.3 (2) | C5—O5B—H5B | 103 (2) |
C3—N3—C4 | 123.8 (2) | N1—C6—C5 | 110.2 (2) |
C2—N3—C4 | 112.2 (2) | N1—C6—H6A | 109.6 |
O3—C3—N3 | 120.6 (2) | C5—C6—H6A | 109.6 |
O3—C3—C3A | 121.8 (2) | N1—C6—H6B | 109.6 |
N3—C3—C3A | 117.5 (2) | C5—C6—H6B | 109.6 |
C3—C3A—C3B | 113.3 (2) | H6A—C6—H6B | 108.1 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O5A—H5A···O1i | 0.84 (3) | 2.26 (3) | 2.918 (3) | 136 (3) |
O5B—H5B···O1i | 0.92 (4) | 1.97 (4) | 2.833 (3) | 157 (3) |
Symmetry code: (i) −x, −y, −z. |