Literature DB >> 26870505

Crystal structure of 3-(di-ethyl-amino)-phenol.

James A Golen1, Kyle J McDonald2, David R Manke1.   

Abstract

The title compound, C10H15NO, has two mol-ecules in the asymmetric unit. Each mol-ecule has a near-planar C8NO unit excluding H atoms and the terminal methyl groups on the di-ethyl-amino groups, with mean deviations from planarity of 0.036 and 0.063 Å. In the crystal, hydrogen bonding leads to four-membered O-H⋯O-H⋯O-H·· rings. No π-π inter-actions were observed in the structure.

Entities:  

Keywords:  crystal structure; hydrogen bonding; phenols

Year:  2015        PMID： 26870505      PMCID： PMC4719986          DOI： 10.1107/S2056989015024226

Source DB:  PubMed          Journal:  Acta Crystallogr E Crystallogr Commun


Related literature

For the structure of 3-amino­phenol, see: Allen et al. (1997 ▸). For the structure of similar 3-amino­phenols, see: Xu et al. (2004 ▸); Suchetan et al. (2014 ▸). For background, see: McDonald et al. (2015 ▸); Mills-Robles et al. (2015 ▸); Nguyen et al. (2015 ▸).

Experimental

Crystal data

C10H15NO M = 165.23 Orthorhombic, a = 14.5166 (17) Å b = 15.9102 (18) Å c = 16.0527 (18) Å V = 3707.6 (7) Å3 Z = 16 Cu Kα radiation μ = 0.60 mm−1 T = 120 K 0.25 × 0.2 × 0.1 mm

Data collection

Bruker D8 Venture CMOS diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2014 ▸) T min = 0.679, T max = 0.753 21122 measured reflections 3398 independent reflections 2633 reflections with I > 2σ(I) R int = 0.090

Refinement

R[F 2 > 2σ(F 2)] = 0.042 wR(F 2) = 0.107 S = 1.02 3398 reflections 228 parameters 2 restraints H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.19 e Å−3 Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2014 ▸); cell refinement: SAINT (Bruker, 2014 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▸); software used to prepare material for publication: OLEX2 and publCIF (Westrip, 2010 ▸). Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015024226/ff2147sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015024226/ff2147Isup2.hkl Click here for additional data file. Supporting information file. DOI: 10.1107/S2056989015024226/ff2147Isup3.cml Click here for additional data file. . DOI: 10.1107/S2056989015024226/ff2147fig1.tif Mol­ecular structure of the title compound, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are drawn as spheres of arbitrary radius. Click here for additional data file. . DOI: 10.1107/S2056989015024226/ff2147fig2.tif Mol­ecular packing of the title compound with hydrogen bonding shown as dashed lines. CCDC reference: 1442843 Additional supporting information: crystallographic information; 3D view; checkCIF report
C10H15NOF(000) = 1440
Mr = 165.23Dx = 1.184 Mg m−3
Orthorhombic, PbcaCu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ac 2abCell parameters from 8014 reflections
a = 14.5166 (17) Åθ = 5.0–68.1°
b = 15.9102 (18) ŵ = 0.60 mm−1
c = 16.0527 (18) ÅT = 120 K
V = 3707.6 (7) Å3SHARD, colourless
Z = 160.25 × 0.2 × 0.1 mm
Bruker D8 Venture CMOS diffractometer3398 independent reflections
Radiation source: Cu2633 reflections with I > 2σ(I)
HELIOS MX monochromatorRint = 0.090
φ and ω scansθmax = 68.4°, θmin = 5.0°
Absorption correction: multi-scan (SADABS; Bruker, 2014)h = −17→17
Tmin = 0.679, Tmax = 0.753k = −18→19
21122 measured reflectionsl = −11→19
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.042w = 1/[σ2(Fo2) + (0.0402P)2 + 1.2567P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.107(Δ/σ)max < 0.001
S = 1.02Δρmax = 0.19 e Å−3
3398 reflectionsΔρmin = −0.20 e Å−3
228 parametersExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
2 restraintsExtinction coefficient: 0.0024 (2)
Experimental. Absorption correction: SADABS2014/4 (Bruker,2014/4) was used for absorption correction. wR2(int) was 0.1095 before and 0.0838 after correction. The Ratio of minimum to maximum transmission is 0.9012. The λ/2 correction factor is 0.00150.
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.
xyzUiso*/Ueq
O10.53496 (8)0.52600 (7)0.61994 (7)0.0255 (3)
H10.5319 (14)0.5635 (10)0.5812 (10)0.038*
N10.82785 (10)0.66193 (9)0.66954 (9)0.0271 (3)
C10.61885 (11)0.53018 (10)0.66024 (10)0.0209 (3)
C20.68001 (11)0.59514 (10)0.64446 (10)0.0211 (3)
H20.66390.63790.60580.025*
C30.76619 (12)0.59821 (9)0.68541 (10)0.0214 (4)
C40.78585 (12)0.53347 (10)0.74327 (10)0.0234 (4)
H40.84230.53420.77320.028*
C50.72339 (12)0.46927 (10)0.75652 (10)0.0249 (4)
H50.73850.42600.79500.030*
C60.63954 (12)0.46591 (10)0.71552 (10)0.0250 (4)
H60.59760.42110.72490.030*
C70.92033 (12)0.66198 (11)0.70474 (11)0.0281 (4)
H7A0.96310.68840.66440.034*
H7B0.94050.60310.71300.034*
C80.92687 (14)0.70839 (12)0.78718 (12)0.0367 (5)
H8A0.99100.70890.80610.055*
H8B0.88850.68000.82870.055*
H8C0.90530.76630.77990.055*
C90.80758 (12)0.72813 (10)0.60980 (11)0.0275 (4)
H9A0.84600.77780.62300.033*
H9B0.74220.74480.61590.033*
C100.82475 (13)0.70291 (11)0.52001 (11)0.0323 (4)
H10A0.81670.75200.48380.048*
H10B0.78090.65900.50380.048*
H10C0.88770.68140.51440.048*
O1A0.50614 (8)0.61366 (7)0.47501 (7)0.0254 (3)
N1A0.63804 (10)0.88712 (8)0.50028 (8)0.0238 (3)
C1A0.55769 (11)0.67627 (9)0.43824 (10)0.0196 (3)
H1A0.4968 (13)0.5730 (9)0.4404 (10)0.029*
C2A0.57128 (10)0.74811 (9)0.48544 (9)0.0186 (3)
H2A0.54580.75170.53980.022*
C3A0.62260 (11)0.81588 (9)0.45334 (9)0.0188 (3)
C4A0.65707 (11)0.80848 (10)0.37146 (10)0.0214 (4)
H4A0.69050.85360.34730.026*
C5A0.64237 (11)0.73569 (10)0.32641 (10)0.0234 (4)
H5A0.66690.73170.27170.028*
C6A0.59298 (11)0.66813 (10)0.35830 (10)0.0228 (4)
H6A0.58370.61840.32660.027*
C7A0.68674 (12)0.95955 (10)0.46599 (11)0.0249 (4)
H7AA0.66781.01050.49690.030*
H7AB0.66810.96710.40710.030*
C8A0.79083 (12)0.95156 (11)0.47007 (11)0.0303 (4)
H8AA0.81921.00410.45120.045*
H8AB0.81090.90530.43400.045*
H8AC0.80960.94010.52760.045*
C9A0.61651 (12)0.89193 (10)0.58880 (10)0.0248 (4)
H9AA0.66640.92300.61750.030*
H9AB0.61500.83430.61200.030*
C10A0.52551 (13)0.93469 (12)0.60712 (12)0.0358 (5)
H10D0.51790.94050.66750.054*
H10E0.47500.90080.58460.054*
H10F0.52480.99040.58120.054*
U11U22U33U12U13U23
O10.0246 (7)0.0244 (6)0.0276 (6)−0.0063 (5)−0.0026 (5)0.0020 (5)
N10.0210 (8)0.0279 (7)0.0323 (8)−0.0061 (6)−0.0042 (6)0.0053 (6)
C10.0211 (8)0.0223 (7)0.0194 (8)−0.0007 (6)0.0019 (6)−0.0043 (6)
C20.0241 (9)0.0198 (7)0.0195 (8)−0.0003 (6)0.0016 (6)0.0001 (6)
C30.0219 (9)0.0206 (8)0.0216 (8)0.0001 (6)0.0037 (6)−0.0036 (6)
C40.0244 (9)0.0252 (8)0.0207 (8)0.0035 (7)−0.0003 (6)−0.0032 (7)
C50.0321 (10)0.0226 (8)0.0201 (8)0.0048 (7)0.0047 (7)0.0007 (6)
C60.0301 (10)0.0202 (8)0.0246 (8)−0.0022 (7)0.0063 (7)0.0005 (7)
C70.0199 (9)0.0336 (9)0.0309 (9)−0.0044 (7)0.0002 (7)0.0002 (7)
C80.0406 (12)0.0394 (10)0.0300 (10)−0.0106 (9)−0.0043 (8)−0.0004 (8)
C90.0240 (9)0.0203 (8)0.0381 (10)−0.0041 (7)−0.0009 (7)0.0027 (7)
C100.0258 (10)0.0330 (9)0.0379 (10)−0.0002 (8)0.0024 (8)0.0072 (8)
O1A0.0278 (7)0.0209 (6)0.0274 (6)−0.0078 (5)−0.0013 (5)0.0007 (5)
N1A0.0287 (8)0.0206 (7)0.0222 (7)−0.0052 (6)0.0038 (6)−0.0041 (5)
C1A0.0147 (8)0.0192 (7)0.0249 (8)−0.0013 (6)−0.0026 (6)0.0033 (6)
C2A0.0155 (8)0.0218 (8)0.0185 (8)0.0015 (6)−0.0001 (6)0.0004 (6)
C3A0.0160 (8)0.0192 (7)0.0211 (8)0.0004 (6)−0.0022 (6)−0.0006 (6)
C4A0.0192 (9)0.0227 (8)0.0223 (8)−0.0026 (6)0.0002 (6)0.0015 (6)
C5A0.0218 (9)0.0294 (8)0.0190 (8)0.0006 (7)0.0017 (6)−0.0020 (7)
C6A0.0222 (9)0.0220 (8)0.0243 (8)0.0010 (6)−0.0034 (7)−0.0055 (6)
C7A0.0263 (9)0.0163 (7)0.0319 (9)−0.0037 (7)0.0029 (7)−0.0027 (6)
C8A0.0281 (10)0.0327 (9)0.0302 (9)−0.0079 (7)0.0018 (7)−0.0062 (7)
C9A0.0271 (10)0.0269 (8)0.0202 (8)−0.0015 (7)−0.0025 (7)−0.0050 (6)
C10A0.0320 (11)0.0408 (10)0.0348 (10)0.0041 (9)0.0066 (8)−0.0080 (8)
O1—H10.863 (9)O1A—C1A1.3786 (19)
O1—C11.381 (2)O1A—H1A0.863 (9)
N1—C31.376 (2)N1A—C3A1.379 (2)
N1—C71.457 (2)N1A—C7A1.460 (2)
N1—C91.455 (2)N1A—C9A1.457 (2)
C1—C21.386 (2)C1A—C2A1.385 (2)
C1—C61.387 (2)C1A—C6A1.388 (2)
C2—H20.9500C2A—H2A0.9500
C2—C31.414 (2)C2A—C3A1.408 (2)
C3—C41.416 (2)C3A—C4A1.411 (2)
C4—H40.9500C4A—H4A0.9500
C4—C51.382 (2)C4A—C5A1.382 (2)
C5—H50.9500C5A—H5A0.9500
C5—C61.385 (2)C5A—C6A1.390 (2)
C6—H60.9500C6A—H6A0.9500
C7—H7A0.9900C7A—H7AA0.9900
C7—H7B0.9900C7A—H7AB0.9900
C7—C81.518 (2)C7A—C8A1.518 (2)
C8—H8A0.9800C8A—H8AA0.9800
C8—H8B0.9800C8A—H8AB0.9800
C8—H8C0.9800C8A—H8AC0.9800
C9—H9A0.9900C9A—H9AA0.9900
C9—H9B0.9900C9A—H9AB0.9900
C9—C101.517 (3)C9A—C10A1.515 (2)
C10—H10A0.9800C10A—H10D0.9800
C10—H10B0.9800C10A—H10E0.9800
C10—H10C0.9800C10A—H10F0.9800
C1—O1—H1110.5 (14)C1A—O1A—H1A110.6 (13)
C3—N1—C7121.88 (14)C3A—N1A—C7A121.42 (13)
C3—N1—C9121.59 (14)C3A—N1A—C9A122.76 (13)
C9—N1—C7116.22 (14)C9A—N1A—C7A115.48 (13)
O1—C1—C2121.02 (14)O1A—C1A—C2A116.05 (14)
O1—C1—C6117.09 (14)O1A—C1A—C6A121.93 (14)
C2—C1—C6121.88 (15)C2A—C1A—C6A122.02 (14)
C1—C2—H2119.7C1A—C2A—H2A119.8
C1—C2—C3120.50 (15)C1A—C2A—C3A120.46 (14)
C3—C2—H2119.7C3A—C2A—H2A119.8
N1—C3—C2120.99 (14)N1A—C3A—C2A121.02 (14)
N1—C3—C4121.75 (15)N1A—C3A—C4A121.31 (14)
C2—C3—C4117.26 (15)C2A—C3A—C4A117.67 (14)
C3—C4—H4119.8C3A—C4A—H4A119.9
C5—C4—C3120.41 (16)C5A—C4A—C3A120.17 (15)
C5—C4—H4119.8C5A—C4A—H4A119.9
C4—C5—H5118.9C4A—C5A—H5A118.8
C4—C5—C6122.14 (16)C4A—C5A—C6A122.35 (15)
C6—C5—H5118.9C6A—C5A—H5A118.8
C1—C6—H6121.1C1A—C6A—C5A117.31 (14)
C5—C6—C1117.77 (15)C1A—C6A—H6A121.3
C5—C6—H6121.1C5A—C6A—H6A121.3
N1—C7—H7A108.9N1A—C7A—H7AA108.9
N1—C7—H7B108.9N1A—C7A—H7AB108.9
N1—C7—C8113.32 (15)N1A—C7A—C8A113.57 (14)
H7A—C7—H7B107.7H7AA—C7A—H7AB107.7
C8—C7—H7A108.9C8A—C7A—H7AA108.9
C8—C7—H7B108.9C8A—C7A—H7AB108.9
C7—C8—H8A109.5C7A—C8A—H8AA109.5
C7—C8—H8B109.5C7A—C8A—H8AB109.5
C7—C8—H8C109.5C7A—C8A—H8AC109.5
H8A—C8—H8B109.5H8AA—C8A—H8AB109.5
H8A—C8—H8C109.5H8AA—C8A—H8AC109.5
H8B—C8—H8C109.5H8AB—C8A—H8AC109.5
N1—C9—H9A108.8N1A—C9A—H9AA108.9
N1—C9—H9B108.8N1A—C9A—H9AB108.9
N1—C9—C10113.69 (14)N1A—C9A—C10A113.58 (15)
H9A—C9—H9B107.7H9AA—C9A—H9AB107.7
C10—C9—H9A108.8C10A—C9A—H9AA108.9
C10—C9—H9B108.8C10A—C9A—H9AB108.9
C9—C10—H10A109.5C9A—C10A—H10D109.5
C9—C10—H10B109.5C9A—C10A—H10E109.5
C9—C10—H10C109.5C9A—C10A—H10F109.5
H10A—C10—H10B109.5H10D—C10A—H10E109.5
H10A—C10—H10C109.5H10D—C10A—H10F109.5
H10B—C10—H10C109.5H10E—C10A—H10F109.5
O1—C1—C2—C3−179.26 (14)O1A—C1A—C2A—C3A−179.69 (14)
O1—C1—C6—C5−179.92 (14)O1A—C1A—C6A—C5A178.67 (14)
N1—C3—C4—C5−178.55 (15)N1A—C3A—C4A—C5A178.57 (15)
C1—C2—C3—N1179.29 (15)C1A—C2A—C3A—N1A−178.81 (15)
C1—C2—C3—C4−1.0 (2)C1A—C2A—C3A—C4A1.6 (2)
C2—C1—C6—C51.4 (2)C2A—C1A—C6A—C5A−0.6 (2)
C2—C3—C4—C51.7 (2)C2A—C3A—C4A—C5A−1.8 (2)
C3—N1—C7—C8−92.09 (19)C3A—N1A—C7A—C8A−83.25 (19)
C3—N1—C9—C10−81.0 (2)C3A—N1A—C9A—C10A−98.73 (19)
C3—C4—C5—C6−1.0 (2)C3A—C4A—C5A—C6A0.9 (2)
C4—C5—C6—C1−0.6 (2)C4A—C5A—C6A—C1A0.3 (2)
C6—C1—C2—C3−0.6 (2)C6A—C1A—C2A—C3A−0.4 (2)
C7—N1—C3—C2−173.91 (15)C7A—N1A—C3A—C2A−176.56 (15)
C7—N1—C3—C46.4 (2)C7A—N1A—C3A—C4A3.0 (2)
C7—N1—C9—C1092.77 (18)C7A—N1A—C9A—C10A87.86 (18)
C9—N1—C3—C2−0.5 (2)C9A—N1A—C3A—C2A10.4 (2)
C9—N1—C3—C4179.73 (15)C9A—N1A—C3A—C4A−169.98 (15)
C9—N1—C7—C894.20 (18)C9A—N1A—C7A—C8A90.25 (18)
D—H···AD—HH···AD···AD—H···A
O1—H1···O1A0.86 (1)1.92 (1)2.7445 (16)160 (2)
O1A—H1A···O1i0.86 (1)1.91 (1)2.7599 (16)170 (2)
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A D⋯A D—H⋯A
O1—H1⋯O1A 0.86 (1)1.92 (1)2.7445 (16)160 (2)
O1A—H1A⋯O1i 0.86 (1)1.91 (1)2.7599 (16)170 (2)

Symmetry code: (i) .

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1.  A short history of SHELX.

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Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  Crystal structure refinement with SHELXL.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr C Struct Chem       Date:  2015-01-01       Impact factor: 1.172

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