Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
In the structure of the title compound, C15H18N2O3, the two benzene rings are linked by an ethereal chain, forming a non-coplanar structure. The crystal structure exhibits a layer formation. The structure displays N—H...O, N—H...N and O—H...N hydrogen bonding.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807017503/at2269sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807017503/at2269Isup2.hkl
Contains datablock I

CCDC reference: 647583

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.049
  • wR factor = 0.146
  • Data-to-parameter ratio = 13.4

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT417_ALERT_2_B Short Inter D-H..H-D H2B .. H2C .. 1.60 Ang.
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT165_ALERT_3_C Nr. of Status R Flagged Non-Hydrogen Atoms ..... 1 PLAT417_ALERT_2_C Short Inter D-H..H-D H1B .. H1B .. 2.10 Ang. PLAT420_ALERT_2_C D-H Without Acceptor N2 - H2A ... ? PLAT480_ALERT_4_C Long H...A H-Bond Reported H1B .. N1 .. 2.66 Ang. PLAT751_ALERT_4_C Bond Calc 1.42178, Rep 1.422(2) ...... Senseless su C8 -O2 1.555 1.555 PLAT751_ALERT_4_C Bond Calc 1.51661, Rep 1.516(2) ...... Senseless su C8 -C9 1.555 1.555 PLAT752_ALERT_4_C Angle Calc 108.08, Rep 108.08(8) ...... Senseless su O1 -C7 -C8 1.555 1.555 1.555 PLAT752_ALERT_4_C Angle Calc 111.14, Rep 111.14(8) ...... Senseless su O2 -C8 -C7 1.555 1.555 1.555 PLAT752_ALERT_4_C Angle Calc 112.08, Rep 112.07(13) ...... Senseless su O2 -C8 -C9 1.555 1.555 1.555 PLAT752_ALERT_4_C Angle Calc 111.00, Rep 110.99(10) ...... Senseless su C7 -C8 -C9 1.555 1.555 1.555 PLAT752_ALERT_4_C Angle Calc 109.09, Rep 109.11(15) ...... Senseless su O3 -C9 -C8 1.555 1.555 1.555 PLAT753_ALERT_4_C Torsion Calc 70.26, Rep 70.28(11) ...... Senseless su O1 -C7 -C8 -O2 1.555 1.555 1.555 1.555 PLAT753_ALERT_4_C Torsion Calc -164.27, Rep -164.28(16) ...... Senseless su O1 -C7 -C8 -C9 1.555 1.555 1.555 1.555 PLAT753_ALERT_4_C Torsion Calc 65.35, Rep 65.35(19) ...... Senseless su O2 -C8 -C9 -O3 1.555 1.555 1.555 1.555 PLAT753_ALERT_4_C Torsion Calc -59.58, Rep -59.57(16) ...... Senseless su C7 -C8 -C9 -O3 1.555 1.555 1.555 1.555 PLAT753_ALERT_4_C Torsion Calc -171.17, Rep -171.17(12) ...... Senseless su C8 -C7 -O1 -C6 1.555 1.555 1.555 1.555 PLAT753_ALERT_4_C Torsion Calc 132.46, Rep 132.46(17) ...... Senseless su C8 -C9 -O3 -C10 1.555 1.555 1.555 1.555
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 18 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 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 14 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

Diamine compounds not only are the materials of preparing dyes, paints, oil dope, but also are the important intermediate of synthesizing Schiff base compounds. Recently, Schiff base metal complexes have been widely investigated for their properties and applications in different fields, such as catalysis (Sabater et al., 2001) and materials chemistry (Lacroix 2001).These compounds anchored covalently to various substrates by hydroxy-functioned represents one of the most interesting issues(Bella et al., 2004). Here, the title compound (I) (1,3-bis(2-aminophenoxy)-2-propanol) was prepared from o-nitrophenol and epichlorohydrin, by etherization and reduction of nitro group.

In the crystal structure of the title compound (I), the two phenyl rings were linked by ethereal chain forming a non-coplanar structure (Fig. 1). Layers are formed by the intermolecular hydrogen bonds, and the aryl rings in different molecules are approximately parallel to each other. The O2 atom of the hydroxy group in (I) form two intermolecular hydrogen bonds with the N1 and N2 atoms of two adjeacent molecules, respectively (Fig. 2). The O2 atom is doubly hydrogen bridged. The N2···O2···N1 angle is about 112°. Thus, the molecular packing is controlled by hydrogen bonding interactions.

Related literature top

For related literature, see: Bella et al. (2004); Lacroix (2001); Sabater et al. (2001).

Experimental top

80% Hydrazine hydrate (4.5 g, 72 mmol, 2.0 equiv.) was added slowly, whilst stirring, to a ethanol solution containing 1,3-bis(2-nitrophenoxy)-2-propanol (3.0 g, 9 mmol), FeCl3.6H2O (0.8 g) and active carbon (1.8 g). The mixture was heated, and stirring for about 2 h. The black residue was removed from the solution by filtration, and then the solvent was removed under reduced pressure. The crude product was purified by column chromatography over silica gel using 20% EtOAc-hexane to afford pure yellow crystals, 1.7 g, in a yield of 69%. Single crystals of (I) suitable for X-ray diffraction were obtained from an ethanol-CH2Cl2 mixture by slow evaporation at room temperature.

Refinement top

The H atoms in hydroxy group were located in a difference Fourier map and refine in their as-found positions relative to O atoms with Uiso(H) = 1.2Ueq(O). Other H atoms were placed in calculated positions with C—H = 0.93–0.97 Å and N—H = 0.86 Å, and refined using a riding model. Uiso(H) = 1.2–1.5Ueq(C,N).

Structure description top

Diamine compounds not only are the materials of preparing dyes, paints, oil dope, but also are the important intermediate of synthesizing Schiff base compounds. Recently, Schiff base metal complexes have been widely investigated for their properties and applications in different fields, such as catalysis (Sabater et al., 2001) and materials chemistry (Lacroix 2001).These compounds anchored covalently to various substrates by hydroxy-functioned represents one of the most interesting issues(Bella et al., 2004). Here, the title compound (I) (1,3-bis(2-aminophenoxy)-2-propanol) was prepared from o-nitrophenol and epichlorohydrin, by etherization and reduction of nitro group.

In the crystal structure of the title compound (I), the two phenyl rings were linked by ethereal chain forming a non-coplanar structure (Fig. 1). Layers are formed by the intermolecular hydrogen bonds, and the aryl rings in different molecules are approximately parallel to each other. The O2 atom of the hydroxy group in (I) form two intermolecular hydrogen bonds with the N1 and N2 atoms of two adjeacent molecules, respectively (Fig. 2). The O2 atom is doubly hydrogen bridged. The N2···O2···N1 angle is about 112°. Thus, the molecular packing is controlled by hydrogen bonding interactions.

For related literature, see: Bella et al. (2004); Lacroix (2001); Sabater et al. (2001).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. packing diagram of (I). Hydrogen bonds are shown as dashed lines.
1,3-Bis(2-aminophenoxy)-2-propanol top
Crystal data top
C15H18N2O3F(000) = 584
Mr = 274.31Dx = 1.327 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2382 reflections
a = 14.069 (2) Åθ = 1.5–25.0°
b = 5.8636 (9) ŵ = 0.09 mm1
c = 17.112 (3) ÅT = 293 K
β = 103.418 (7)°Prism, yellow
V = 1373.2 (4) Å30.21 × 0.17 × 0.14 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
2382 independent reflections
Radiation source: fine-focus sealed tube1780 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
φ and ω scansθmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
h = 1615
Tmin = 0.981, Tmax = 0.987k = 65
9223 measured reflectionsl = 2020
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)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146H-atom parameters constrained
S = 1.10 w = 1/[σ2(Fo2) + (0.0761P)2 + 0.31P]
where P = (Fo2 + 2Fc2)/3
2382 reflections(Δ/σ)max < 0.001
178 parametersΔρmax = 0.47 e Å3
0 restraintsΔρmin = 0.44 e Å3
Crystal data top
C15H18N2O3V = 1373.2 (4) Å3
Mr = 274.31Z = 4
Monoclinic, P21/cMo Kα radiation
a = 14.069 (2) ŵ = 0.09 mm1
b = 5.8636 (9) ÅT = 293 K
c = 17.112 (3) Å0.21 × 0.17 × 0.14 mm
β = 103.418 (7)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
2382 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
1780 reflections with I > 2σ(I)
Tmin = 0.981, Tmax = 0.987Rint = 0.024
9223 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0490 restraints
wR(F2) = 0.146H-atom parameters constrained
S = 1.10Δρmax = 0.47 e Å3
2382 reflectionsΔρmin = 0.44 e Å3
178 parameters
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*/Ueq
C10.81149 (16)0.0370 (4)1.01642 (11)0.0407 (5)
C20.74359 (18)0.1889 (4)1.03225 (13)0.0521 (6)
H20.76470.31471.06480.063*
C30.64443 (19)0.1577 (5)1.00061 (14)0.0597 (7)
H30.59970.26241.01170.072*
C40.61236 (18)0.0277 (5)0.95297 (15)0.0618 (7)
H40.54580.05060.93280.074*
C50.67907 (16)0.1809 (4)0.93479 (13)0.0518 (6)
H50.65730.30600.90210.062*
C60.77767 (14)0.1480 (4)0.96517 (11)0.0385 (5)
C70.82321 (10)0.4514 (2)0.88735 (8)0.0396 (5)
H7A0.78340.56900.90370.048*
H7B0.78560.38030.83880.048*
C80.91478 (10)0.5536 (2)0.87210 (8)0.0372 (5)
H80.95730.59190.92440.045*
C90.89298 (15)0.7733 (3)0.82454 (12)0.0405 (5)
H9A0.86430.88360.85450.049*
H9B0.95300.83710.81530.049*
C100.74699 (14)0.8723 (3)0.72770 (11)0.0354 (5)
C110.65635 (15)0.7980 (4)0.73339 (13)0.0492 (6)
H110.64970.65630.75600.059*
C120.57499 (18)0.9325 (5)0.70570 (15)0.0610 (7)
H120.51350.88250.70960.073*
C130.58582 (18)1.1407 (5)0.67236 (14)0.0604 (7)
H130.53121.23170.65320.072*
C140.67606 (17)1.2160 (4)0.66696 (13)0.0512 (6)
H140.68191.35800.64430.061*
C150.75904 (14)1.0847 (3)0.69467 (10)0.0364 (5)
N10.91044 (15)0.0606 (4)1.04645 (13)0.0733 (7)
H1A0.93280.17461.07680.088*
H1B0.95000.03871.03490.088*
N20.85195 (13)1.1623 (3)0.69122 (10)0.0459 (5)
H2A0.85871.29460.67150.055*
H2B0.90231.07770.70880.055*
O10.85053 (10)0.2843 (2)0.94980 (8)0.0464 (4)
O20.96575 (9)0.3940 (2)0.83438 (8)0.0430 (4)
H2C1.01550.45350.82660.064*
O30.82630 (10)0.7260 (2)0.74908 (7)0.0414 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0495 (13)0.0407 (13)0.0340 (10)0.0012 (10)0.0137 (9)0.0010 (9)
C20.0749 (17)0.0417 (14)0.0452 (12)0.0087 (12)0.0248 (12)0.0035 (10)
C30.0668 (17)0.0579 (17)0.0619 (14)0.0267 (14)0.0298 (13)0.0086 (13)
C40.0450 (14)0.0731 (19)0.0681 (15)0.0120 (13)0.0150 (12)0.0047 (14)
C50.0443 (13)0.0573 (15)0.0519 (12)0.0022 (12)0.0075 (10)0.0082 (12)
C60.0424 (12)0.0379 (12)0.0360 (10)0.0050 (10)0.0108 (9)0.0008 (9)
C70.0431 (12)0.0365 (12)0.0385 (10)0.0043 (10)0.0079 (9)0.0070 (9)
C80.0389 (11)0.0347 (12)0.0382 (10)0.0043 (9)0.0092 (9)0.0035 (9)
C90.0442 (12)0.0311 (11)0.0438 (11)0.0009 (9)0.0054 (9)0.0027 (9)
C100.0387 (12)0.0322 (12)0.0347 (10)0.0055 (9)0.0075 (8)0.0007 (9)
C110.0464 (14)0.0485 (14)0.0538 (12)0.0002 (11)0.0140 (10)0.0070 (11)
C120.0404 (13)0.0744 (19)0.0682 (15)0.0035 (13)0.0123 (11)0.0030 (14)
C130.0481 (15)0.0671 (18)0.0634 (15)0.0233 (13)0.0076 (12)0.0076 (14)
C140.0601 (15)0.0419 (14)0.0504 (13)0.0144 (12)0.0104 (11)0.0104 (10)
C150.0429 (12)0.0341 (12)0.0328 (9)0.0045 (10)0.0103 (8)0.0014 (9)
N10.0546 (13)0.0726 (16)0.0848 (15)0.0004 (11)0.0002 (11)0.0421 (13)
N20.0504 (11)0.0350 (11)0.0530 (10)0.0024 (9)0.0136 (8)0.0103 (8)
O10.0404 (8)0.0469 (9)0.0497 (8)0.0050 (7)0.0062 (7)0.0189 (7)
O20.0381 (8)0.0388 (9)0.0551 (8)0.0061 (7)0.0169 (6)0.0065 (7)
O30.0465 (9)0.0337 (8)0.0413 (8)0.0091 (7)0.0049 (6)0.0019 (6)
Geometric parameters (Å, º) top
C1—N11.375 (3)C9—H9A0.9700
C1—C21.378 (3)C9—H9B0.9700
C1—C61.407 (3)C10—C111.372 (3)
C2—C31.387 (3)C10—O31.388 (2)
C2—H20.9300C10—C151.394 (3)
C3—C41.371 (4)C11—C121.380 (3)
C3—H30.9300C11—H110.9300
C4—C51.386 (3)C12—C131.371 (4)
C4—H40.9300C12—H120.9300
C5—C61.377 (3)C13—C141.367 (3)
C5—H50.9300C13—H130.9300
C6—O11.373 (2)C14—C151.387 (3)
C7—O11.4350 (19)C14—H140.9300
C7—C81.4978C15—N21.398 (3)
C7—H7A0.9700N1—H1A0.8600
C7—H7B0.9700N1—H1B0.8600
C8—O21.422 (2)N2—H2A0.8600
C8—C91.516 (2)N2—H2B0.8600
C8—H80.9800O2—H2C0.8200
C9—O31.436 (2)
N1—C1—C2123.3 (2)C8—C9—H9A109.9
N1—C1—C6118.52 (19)O3—C9—H9B109.9
C2—C1—C6118.1 (2)C8—C9—H9B109.9
C1—C2—C3121.2 (2)H9A—C9—H9B108.3
C1—C2—H2119.4C11—C10—O3119.26 (19)
C3—C2—H2119.4C11—C10—C15120.98 (19)
C4—C3—C2120.0 (2)O3—C10—C15119.54 (17)
C4—C3—H3120.0C10—C11—C12120.3 (2)
C2—C3—H3120.0C10—C11—H11119.9
C3—C4—C5120.1 (2)C12—C11—H11119.9
C3—C4—H4120.0C13—C12—C11119.2 (2)
C5—C4—H4120.0C13—C12—H12120.4
C6—C5—C4120.0 (2)C11—C12—H12120.4
C6—C5—H5120.0C14—C13—C12120.7 (2)
C4—C5—H5120.0C14—C13—H13119.7
O1—C6—C5125.27 (19)C12—C13—H13119.7
O1—C6—C1114.13 (17)C13—C14—C15121.2 (2)
C5—C6—C1120.6 (2)C13—C14—H14119.4
O1—C7—C8108.08 (8)C15—C14—H14119.4
O1—C7—H7A110.1C14—C15—C10117.6 (2)
C8—C7—H7A110.1C14—C15—N2121.7 (2)
O1—C7—H7B110.1C10—C15—N2120.70 (17)
C8—C7—H7B110.1C1—N1—H1A120.0
H7A—C7—H7B108.4C1—N1—H1B120.0
O2—C8—C7111.14 (8)H1A—N1—H1B120.0
O2—C8—C9112.07 (13)C15—N2—H2A120.0
C7—C8—C9110.99 (10)C15—N2—H2B120.0
O2—C8—H8107.5H2A—N2—H2B120.0
C7—C8—H8107.5C6—O1—C7117.22 (13)
C9—C8—H8107.5C8—O2—H2C109.5
O3—C9—C8109.11 (15)C10—O3—C9115.81 (15)
O3—C9—H9A109.9
N1—C1—C2—C3179.9 (2)C15—C10—C11—C120.5 (3)
C6—C1—C2—C31.8 (3)C10—C11—C12—C130.1 (4)
C1—C2—C3—C40.3 (4)C11—C12—C13—C140.5 (4)
C2—C3—C4—C51.6 (4)C12—C13—C14—C150.2 (4)
C3—C4—C5—C60.5 (4)C13—C14—C15—C100.5 (3)
C4—C5—C6—O1178.3 (2)C13—C14—C15—N2178.43 (19)
C4—C5—C6—C11.7 (3)C11—C10—C15—C140.8 (3)
N1—C1—C6—O11.2 (3)O3—C10—C15—C14173.84 (17)
C2—C1—C6—O1177.11 (17)C11—C10—C15—N2178.09 (18)
N1—C1—C6—C5178.8 (2)O3—C10—C15—N27.3 (3)
C2—C1—C6—C52.9 (3)C5—C6—O1—C710.7 (3)
O1—C7—C8—O270.28 (11)C1—C6—O1—C7169.24 (16)
O1—C7—C8—C9164.28 (16)C8—C7—O1—C6171.17 (12)
O2—C8—C9—O365.35 (19)C11—C10—O3—C9105.4 (2)
C7—C8—C9—O359.57 (16)C15—C10—O3—C979.9 (2)
O3—C10—C11—C12174.1 (2)C8—C9—O3—C10132.46 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O2i0.862.243.061 (2)161
N1—H1B···N1i0.862.663.353 (4)139
N2—H2B···O2ii0.862.413.125 (2)142
O2—H2C···N2iii0.822.313.125 (2)173
Symmetry codes: (i) x+2, y, z+2; (ii) x+2, y+1/2, z+3/2; (iii) x+2, y1/2, z+3/2.

Experimental details

Crystal data
Chemical formulaC15H18N2O3
Mr274.31
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)14.069 (2), 5.8636 (9), 17.112 (3)
β (°) 103.418 (7)
V3)1373.2 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.21 × 0.17 × 0.14
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2002)
Tmin, Tmax0.981, 0.987
No. of measured, independent and
observed [I > 2σ(I)] reflections
9223, 2382, 1780
Rint0.024
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.146, 1.10
No. of reflections2382
No. of parameters178
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.47, 0.44

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O2i0.862.243.061 (2)160.7
N1—H1B···N1i0.862.663.353 (4)138.5
N2—H2B···O2ii0.862.413.125 (2)141.5
O2—H2C···N2iii0.822.313.125 (2)173.1
Symmetry codes: (i) x+2, y, z+2; (ii) x+2, y+1/2, z+3/2; (iii) x+2, y1/2, z+3/2.
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds