5,5-Di­hydroxy-1,3-dipropionyl-1,3-di­aza­cyclo­hexane

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.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](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

---

Computing details

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).

(I)

Crystal data

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) Å^3	Thick plate, colorless
Z = 8	0.11 × 0.35 × 0.40 mm

Data collection

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

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.135	H atoms treated by a mixture of independent and constrained refinement
S = 1.24	w = 1/[σ^2(Fo^2) + (0.0406P)^2 + 2.4823P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
O5A—H5A···O1^i	0.84 (3)	2.26 (3)	2.918 (3)	136 (3)
O5B—H5B···O1^i	0.92 (4)	1.97 (4)	2.833 (3)	157 (3)

Symmetry code: (i) −x, −y, −z.