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

Bai, G.-Y.; Zhang, C.-F.; Zhang, Y.-C.; Zeng, T.; Li, J.-S.

doi:10.1107/S1600536806054389

addenda and errata

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 63| Part 1| January 2007| Pages e2-e3

https://doi.org/10.1107/S1600536806054389

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

Guo-Yi Bai,^a ^* Chen-Fang Zhang,^a Yue-Cheng Zhang,^b Tao Zeng ^b and Jiang-Sheng Li ^b

^aCollege of Chemistry & Environmental Science, Hebei University, Hebei 071002, People's Republic of China, and ^bSchool of Chemical Engineering and Technology, Tianjin University, Tianjin 300072, People's Republic of China
^*Correspondence e-mail: baiguoyi@hotmail.com

(Received 17 September 2006; accepted 14 December 2006; online 20 December 2006)

In the paper by Bai, Zhang, Zhang, Zeng & Li [Acta Cryst. (2006), E62, o2173–o2174], the data relate to the R,R rather than the S,S enantiomer. The revised ellipsoid plot, packing diagram and selected geometrical data are given here.

Figure 1
The molecular structure of (I), with the atom-numbering scheme and 30% probability displacement ellipsoids.

Figure 2
Packing diagram for (I), with hydrogen bonds shown as dashed lines.

2. Experimental

2.1.2. Data collection

R_int = 0.029

2.1.3. Refinement

w = 1/[σ²(F_o²) + (0.0546P)² + 0.0456P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max = 0.002
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

O1—C1	1.419 (3)

C2—N1—C5	115.4 (2)
N1—C2—C1	108.3 (2)
N1—C5—C6	109.7 (2)

O1—C1—C2—N1	−61.4 (3)
N1—C2—C3—C4	−162.1 (3)
N1—C5—C6—N2	173.0 (2)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N2ⁱ	0.93 (5)	1.95 (5)	2.877 (3)	174 (3)
O2—H2B⋯N1ⁱⁱ	0.96 (4)	1.82 (4)	2.767 (3)	174 (3)
N1—H1C⋯O2ⁱⁱⁱ	0.85 (3)	2.23 (3)	3.014 (3)	153 (3)
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+1]$ ; (ii) $[2-x, y+{\script{1\over 2}}, -z+1]$ ; (iii) x-1, y, z.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536806054389/sj9043sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536806054389/sj9043Isup2.hkl

Computing details top

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)bis-1-butanol top

Crystal data top

C₁₀H₂₄N₂O₂	F(000) = 228
M_r = 204.31	D_x = 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) Å³	0.22 × 0.20 × 0.10 mm
Z = 2

Data collection top

Bruker SMART-1000 CCD area detector diffractometer	1318 independent reflections
Radiation source: fine-focus sealed tube	1049 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
φ and ω scans	θ_max = 26.3°, θ_min = 2.0°
Absorption correction: multi-scan SADABS (Sheldrick, 1996)	h = −8→8
T_min = 0.979, T_max = 0.992	k = −10→6
3317 measured reflections	l = −12→12

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.103	w = 1/[σ²(F_o²) + (0.0546P)² + 0.0456P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.002
1318 reflections	Δρ_max = 0.18 e Å⁻³
141 parameters	Δρ_min = −0.17 e Å⁻³
1 restraint	Absolute structure: Friedel pairs merged
Primary atom site location: structure-invariant direct methods

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

	x	y	z	U_iso*/U_eq
O1	0.1972 (3)	0.7636 (3)	0.6659 (2)	0.0496 (6)
H1	0.145 (5)	0.667 (6)	0.639 (3)	0.074*
O2	1.3357 (3)	1.0029 (3)	0.39638 (19)	0.0421 (5)
H2B	1.376 (4)	1.111 (5)	0.400 (3)	0.063*
N1	0.5708 (3)	0.8209 (3)	0.6068 (2)	0.0303 (5)
H1C	0.481 (4)	0.845 (4)	0.549 (3)	0.036*
N2	0.9494 (3)	0.9540 (3)	0.4033 (2)	0.0316 (5)
H2A	1.036 (4)	0.964 (4)	0.473 (3)	0.038*
C1	0.3535 (3)	0.7352 (3)	0.7597 (3)	0.0373 (7)
H1A	0.3962	0.6269	0.7514	0.045*
H1B	0.3162	0.7489	0.8480	0.045*
C2	0.5125 (3)	0.8485 (3)	0.7386 (2)	0.0319 (6)
H2	0.6188	0.8190	0.8019	0.038*
C3	0.4630 (4)	1.0212 (4)	0.7683 (3)	0.0422 (7)
H3A	0.5529	1.0907	0.7321	0.051*
H3B	0.3398	1.0452	0.7244	0.051*
C4	0.4627 (6)	1.0550 (5)	0.9136 (3)	0.0697 (11)
H4A	0.5803	1.0225	0.9590	0.105*
H4B	0.3623	0.9976	0.9477	0.105*
H4C	0.4453	1.1665	0.9265	0.105*
C5	0.7343 (3)	0.9135 (3)	0.5739 (3)	0.0356 (6)
H5A	0.8345	0.9052	0.6448	0.043*
H5B	0.6998	1.0243	0.5634	0.043*
C6	0.8011 (4)	0.8520 (3)	0.4479 (3)	0.0348 (6)
H6A	0.8492	0.7452	0.4619	0.042*
H6B	0.6962	0.8477	0.3801	0.042*
C7	1.2165 (4)	0.9866 (4)	0.2782 (2)	0.0394 (7)
H7A	1.2866	0.9407	0.2109	0.047*
H7B	1.1730	1.0904	0.2480	0.047*
C8	1.0489 (4)	0.8826 (3)	0.2974 (2)	0.0342 (6)
H8	1.0935	0.7770	0.3254	0.041*
C9	0.9224 (4)	0.8677 (4)	0.1694 (3)	0.0482 (8)
H9A	0.8030	0.8236	0.1888	0.058*
H9B	0.8984	0.9729	0.1333	0.058*
C10	1.0003 (5)	0.7663 (6)	0.0660 (3)	0.0861 (15)
H10A	1.0407	0.6664	0.1040	0.129*
H10B	1.1052	0.8191	0.0334	0.129*
H10C	0.9048	0.7486	−0.0054	0.129*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0365 (11)	0.0386 (12)	0.0726 (14)	−0.0050 (10)	−0.0011 (10)	0.0063 (11)
O2	0.0349 (10)	0.0396 (12)	0.0505 (11)	−0.0049 (9)	−0.0030 (8)	0.0096 (10)
N1	0.0256 (10)	0.0333 (13)	0.0319 (11)	−0.0017 (10)	0.0018 (9)	0.0012 (10)
N2	0.0311 (11)	0.0287 (12)	0.0356 (12)	−0.0047 (10)	0.0056 (9)	−0.0016 (10)
C1	0.0386 (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	0.0348 (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) top

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	106.1 (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	106.0 (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	72.3 (4)
C8—N2—C6—C5	167.6 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2ⁱ	0.93 (5)	1.95 (5)	2.877 (3)	174 (3)
O2—H2B···N1ⁱⁱ	0.96 (4)	1.81 (4)	2.767 (3)	174 (3)
N1—H1C···O2ⁱⁱⁱ	0.85 (3)	2.23 (3)	3.014 (3)	153 (3)

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

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addenda and errata\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

2. Experimental

2.1.2. Data collection

2.1.3. Refinement

Supporting information

addenda and errata

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