(S,S)-2,2′-(1,2-Ethanediyldiimino)dibutan-1-ol

The title compound, C₁₀H₂₄N₂O₂, was synthesized by N-alkyl­ation of 1,2-dichloro­ethane with (S)-2-amino-1-butanol. In the crystal structure, O—H...N and N—H...O link the mol­ecules into sheets in the bc plane.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.041
• wR factor = 0.102
• Data-to-parameter ratio = 9.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.70 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.58 Ratio

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           26.33
           From the CIF: _reflns_number_total               1318
           Count of symmetry unique reflns         1336
           Completeness (_total/calc)             98.65%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

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

(S,S)-2,2'-(1,2-Ethanediyldiimino)dibutan-1-ol

Crystal data

C10H24N2O2	F(000) = 228
Mr = 204.31	Dx = 1.107 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1264 reflections
a = 7.157 (3) Å	θ = 2.9–25.3°
b = 8.440 (4) Å	µ = 0.08 mm^−1
c = 10.193 (5) Å	T = 294 K
β = 95.631 (8)°	Block, colourless
V = 612.7 (5) Å^3	0.22 × 0.20 × 0.10 mm
Z = 2

Data collection

Bruker SMART-1000 CCD area-detector diffractometer	1318 independent reflections
Radiation source: fine-focus sealed tube	1049 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
φ and ω scans	θmax = 26.3°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
Tmin = 0.983, Tmax = 0.992	k = −10→6
3317 measured reflections	l = −12→12

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.102	w = 1/[σ^2(Fo^2) + (0.0537P)^2 + 0.0476P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max = 0.001
1318 reflections	Δρmax = 0.50 e Å^−3
141 parameters	Δρmin = −0.42 e Å^−3
1 restraint	Absolute structure: Friedel pairs merged
Primary atom site location: structure-invariant direct methods

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.8028 (3)	0.2364 (3)	0.3341 (2)	0.0496 (6)
H1	0.855 (5)	0.333 (6)	0.361 (3)	0.074*
O2	−0.3356 (3)	−0.0029 (3)	0.60362 (19)	0.0421 (5)
H2B	−0.376 (4)	−0.111 (5)	0.600 (3)	0.063*
N1	0.4292 (3)	0.1791 (3)	0.3932 (2)	0.0303 (5)
H1C	0.519 (4)	0.155 (4)	0.451 (2)	0.036*
N2	0.0506 (3)	0.0460 (3)	0.5967 (2)	0.0316 (5)
H2A	−0.036 (4)	0.036 (4)	0.527 (3)	0.038*
C1	0.6465 (3)	0.2648 (3)	0.2403 (3)	0.0373 (7)
H1A	0.6838	0.2511	0.1520	0.045*
H1B	0.6038	0.3731	0.2486	0.045*
C2	0.4875 (3)	0.1515 (3)	0.2613 (2)	0.0319 (6)
H2	0.3812	0.1810	0.1981	0.038*
C3	0.5370 (4)	−0.0212 (4)	0.2317 (3)	0.0422 (7)
H3A	0.6602	−0.0452	0.2756	0.051*
H3B	0.4471	−0.0907	0.2679	0.051*
C4	0.5373 (6)	−0.0550 (5)	0.0864 (3)	0.0697 (11)
H4A	0.4197	−0.0226	0.0410	0.105*
H4B	0.5548	−0.1665	0.0735	0.105*
H4C	0.6377	0.0024	0.0523	0.105*
C5	0.2657 (3)	0.0865 (3)	0.4261 (3)	0.0356 (6)
H5A	0.3001	−0.0243	0.4365	0.043*
H5B	0.1655	0.0948	0.3552	0.043*
C6	0.1989 (4)	0.1480 (3)	0.5521 (3)	0.0348 (6)
H6A	0.3038	0.1523	0.6199	0.042*
H6B	0.1508	0.2548	0.5381	0.042*
C7	−0.2165 (4)	0.0134 (4)	0.7218 (2)	0.0394 (7)
H7A	−0.1730	−0.0904	0.7520	0.047*
H7B	−0.2866	0.0593	0.7891	0.047*
C8	−0.0488 (4)	0.1174 (3)	0.7026 (2)	0.0342 (6)
H8	−0.0935	0.2230	0.6746	0.041*
C9	0.0776 (4)	0.1323 (4)	0.8306 (3)	0.0482 (8)
H9A	0.1017	0.0271	0.8667	0.058*
H9B	0.1970	0.1764	0.8112	0.058*
C10	−0.0003 (5)	0.2337 (6)	0.9340 (3)	0.0861 (15)
H10A	−0.0405	0.3336	0.8960	0.129*
H10B	0.0951	0.2513	1.0055	0.129*
H10C	−0.1054	0.1809	0.9665	0.129*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0365 (11)	0.0385 (12)	0.0726 (14)	−0.0050 (10)	−0.0011 (10)	0.0063 (11)
O2	0.0349 (10)	0.0395 (12)	0.0505 (11)	−0.0049 (9)	−0.0031 (8)	0.0096 (10)
N1	0.0256 (10)	0.0333 (13)	0.0319 (11)	−0.0017 (10)	0.0018 (9)	0.0011 (10)
N2	0.0311 (11)	0.0287 (12)	0.0356 (12)	−0.0048 (10)	0.0056 (9)	−0.0016 (10)
C1	0.0387 (15)	0.0332 (16)	0.0416 (15)	0.0007 (13)	0.0120 (12)	0.0038 (12)
C2	0.0333 (13)	0.0322 (15)	0.0305 (13)	0.0050 (12)	0.0040 (11)	0.0025 (11)
C3	0.0461 (15)	0.0341 (16)	0.0472 (16)	0.0037 (14)	0.0087 (13)	−0.0033 (14)
C4	0.095 (3)	0.058 (2)	0.056 (2)	0.019 (2)	0.0038 (19)	−0.0184 (17)
C5	0.0331 (13)	0.0349 (15)	0.0393 (14)	−0.0063 (13)	0.0062 (11)	−0.0039 (12)
C6	0.0341 (13)	0.0305 (14)	0.0407 (14)	−0.0052 (12)	0.0081 (12)	0.0011 (12)
C7	0.0369 (14)	0.0418 (17)	0.0403 (14)	−0.0066 (13)	0.0080 (11)	0.0022 (13)
C8	0.0347 (14)	0.0293 (15)	0.0395 (14)	−0.0025 (12)	0.0091 (12)	0.0013 (12)
C9	0.0426 (16)	0.058 (2)	0.0442 (16)	−0.0096 (16)	0.0061 (13)	−0.0104 (15)
C10	0.075 (2)	0.116 (4)	0.070 (2)	−0.012 (3)	0.019 (2)	−0.045 (3)

Geometric parameters (Å, º)

O1—C1	1.419 (3)	C4—H4B	0.9600
O1—H1	0.93 (5)	C4—H4C	0.9600
O2—C7	1.412 (3)	C5—C6	1.506 (4)
O2—H2B	0.96 (4)	C5—H5A	0.9700
N1—C2	1.464 (3)	C5—H5B	0.9700
N1—C5	1.473 (3)	C6—H6A	0.9700
N1—H1C	0.85 (3)	C6—H6B	0.9700
N2—C6	1.473 (3)	C7—C8	1.515 (4)
N2—C8	1.478 (3)	C7—H7A	0.9700
N2—H2A	0.90 (3)	C7—H7B	0.9700
C1—C2	1.518 (4)	C8—C9	1.519 (4)
C1—H1A	0.9700	C8—H8	0.9800
C1—H1B	0.9700	C9—C10	1.507 (4)
C2—C3	1.536 (4)	C9—H9A	0.9700
C2—H2	0.9800	C9—H9B	0.9700
C3—C4	1.508 (4)	C10—H10A	0.9600
C3—H3A	0.9700	C10—H10B	0.9600
C3—H3B	0.9700	C10—H10C	0.9600
C4—H4A	0.9600
C1—O1—H1	109 (2)	C6—C5—H5A	109.7
C7—O2—H2B	106.2 (19)	N1—C5—H5B	109.7
C2—N1—C5	115.4 (2)	C6—C5—H5B	109.7
C2—N1—H1C	109.3 (17)	H5A—C5—H5B	108.2
C5—N1—H1C	106.3 (19)	N2—C6—C5	111.1 (2)
C6—N2—C8	113.6 (2)	N2—C6—H6A	109.4
C6—N2—H2A	105.9 (17)	C5—C6—H6A	109.4
C8—N2—H2A	105.8 (16)	N2—C6—H6B	109.4
O1—C1—C2	110.6 (2)	C5—C6—H6B	109.4
O1—C1—H1A	109.5	H6A—C6—H6B	108.0
C2—C1—H1A	109.5	O2—C7—C8	111.5 (2)
O1—C1—H1B	109.5	O2—C7—H7A	109.3
C2—C1—H1B	109.5	C8—C7—H7A	109.3
H1A—C1—H1B	108.1	O2—C7—H7B	109.3
N1—C2—C1	108.3 (2)	C8—C7—H7B	109.3
N1—C2—C3	115.1 (2)	H7A—C7—H7B	108.0
C1—C2—C3	112.3 (2)	N2—C8—C7	107.6 (2)
N1—C2—H2	106.9	N2—C8—C9	111.8 (2)
C1—C2—H2	106.9	C7—C8—C9	110.5 (2)
C3—C2—H2	106.9	N2—C8—H8	109.0
C4—C3—C2	113.3 (3)	C7—C8—H8	109.0
C4—C3—H3A	108.9	C9—C8—H8	109.0
C2—C3—H3A	108.9	C10—C9—C8	114.7 (3)
C4—C3—H3B	108.9	C10—C9—H9A	108.6
C2—C3—H3B	108.9	C8—C9—H9A	108.6
H3A—C3—H3B	107.7	C10—C9—H9B	108.6
C3—C4—H4A	109.5	C8—C9—H9B	108.6
C3—C4—H4B	109.5	H9A—C9—H9B	107.6
H4A—C4—H4B	109.5	C9—C10—H10A	109.5
C3—C4—H4C	109.5	C9—C10—H10B	109.5
H4A—C4—H4C	109.5	H10A—C10—H10B	109.5
H4B—C4—H4C	109.5	C9—C10—H10C	109.5
N1—C5—C6	109.7 (2)	H10A—C10—H10C	109.5
N1—C5—H5A	109.7	H10B—C10—H10C	109.5
C5—N1—C2—C1	175.7 (2)	N1—C5—C6—N2	−173.0 (2)
C5—N1—C2—C3	−57.8 (3)	C6—N2—C8—C7	170.5 (2)
O1—C1—C2—N1	61.4 (3)	C6—N2—C8—C9	−68.0 (3)
O1—C1—C2—C3	−66.7 (3)	O2—C7—C8—N2	−57.3 (3)
N1—C2—C3—C4	162.1 (3)	O2—C7—C8—C9	−179.7 (2)
C1—C2—C3—C4	−73.4 (3)	N2—C8—C9—C10	167.9 (3)
C2—N1—C5—C6	−169.3 (2)	C7—C8—C9—C10	−72.2 (4)
C8—N2—C6—C5	−167.6 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2^i	0.93 (5)	1.95 (5)	2.877 (3)	174 (3)
O2—H2B···N1^ii	0.96 (4)	1.82 (4)	2.767 (3)	174 (3)
N1—H1C···O2^iii	0.85 (3)	2.23 (3)	3.014 (3)	153 (3)

Symmetry codes: (i) −x+1, y+1/2, −z+1; (ii) −x, y−1/2, −z+1; (iii) x+1, y, z.