Literature DB >> 23476386

4-(Prop-2-yn-1-yl-oxy)benzaldehyde.

Ikue Doi1, Tsunehisa Okuno.   

Abstract

In the title mol-ecule, C10H8O2, all non-H atoms are essentailly coplanar (r.m.s. deviation = 0.0192 Å), indicating an effective conjugation of the carbonyl group, the benzene ring and the lone pair of the propyn-yloxy O atom. In the crystal, π-π stacking inter-actions [centroid-centroid distance = 3.5585 (15) Å] connect mol-ecules into inversion dimers which are linked by Csp-H⋯O=C hydrogen bonds, forming a ladder-like structure.

Entities:  

Year:  2012        PMID： 23476386      PMCID： PMC3588297          DOI： 10.1107/S1600536812050866

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For related structures of 4-(prop-2-yn-1-yl­oxy)benzenes, see: Berscheid et al. (1992 ▶); Mohr et al. (2003 ▶); Nieger et al. (2004 ▶); Ranjith et al. (2010 ▶); Zhang et al. (2011 ▶).

Experimental

Crystal data

C10H8O2 M = 160.17 Monoclinic, a = 7.906 (3) Å b = 7.385 (2) Å c = 14.036 (5) Å β = 102.025 (5)° V = 801.5 (5) Å3 Z = 4 Mo Kα radiation μ = 0.09 mm−1 T = 93 K 0.20 × 0.10 × 0.10 mm

Data collection

Rigaku Saturn724+ diffractometer Absorption correction: numerical (NUMABS; Rigaku, 1999 ▶) T min = 0.984, T max = 0.991 6309 measured reflections 1832 independent reflections 1669 reflections with F 2 > 2σ(F 2) R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.037 wR(F 2) = 0.101 S = 1.06 1831 reflections 141 parameters H-atom parameters constrained Δρmax = 0.32 e Å−3 Δρmin = −0.17 e Å−3 Data collection: CrystalClear (Rigaku, 2008 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXD (Schneider & Sheldrick, 2002 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 2012 ▶); software used to prepare material for publication: CrystalStructure (Rigaku, 2010 ▶). Click here for additional data file. Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812050866/lh5571sup1.cif Click here for additional data file. Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812050866/lh5571Isup2.hkl Click here for additional data file. Supplementary material file. DOI: 10.1107/S1600536812050866/lh5571Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C10H8O2F(000) = 336.00
Mr = 160.17Dx = 1.327 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2ynCell parameters from 2598 reflections
a = 7.906 (3) Åθ = 2.6–31.1°
b = 7.385 (2) ŵ = 0.09 mm−1
c = 14.036 (5) ÅT = 93 K
β = 102.025 (5)°Prism, colorless
V = 801.5 (5) Å30.20 × 0.10 × 0.10 mm
Z = 4
Rigaku Saturn724+ diffractometer1669 reflections with F2 > 2σ(F2)
Detector resolution: 7.111 pixels mm-1Rint = 0.044
ω scansθmax = 27.5°
Absorption correction: numerical (NUMABS; Rigaku, 1999)h = −10→10
Tmin = 0.984, Tmax = 0.991k = −9→8
6309 measured reflectionsl = −18→13
1832 independent reflections
Refinement on F2Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101H-atom parameters constrained
S = 1.06w = 1/[σ2(Fo2) + (0.0503P)2 + 0.2315P] where P = (Fo2 + 2Fc2)/3
1831 reflections(Δ/σ)max = 0.001
141 parametersΔρmax = 0.32 e Å−3
0 restraintsΔρmin = −0.17 e Å−3
Primary atom site location: structure-invariant direct methods
Refinement. Refinement was performed using all reflections. except for one with very negative F2. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).
xyzUiso*/Ueq
O1−0.02874 (9)0.43434 (11)0.86519 (6)0.0269 (3)
O20.72238 (8)0.20161 (10)1.09425 (5)0.0184 (2)
C10.26055 (12)0.32435 (14)0.90578 (7)0.0169 (3)
C20.39397 (13)0.24978 (14)0.86774 (7)0.0183 (3)
C30.55122 (13)0.20458 (14)0.92785 (7)0.0176 (3)
C40.57337 (12)0.23630 (13)1.02780 (7)0.0160 (3)
C50.43929 (12)0.30938 (13)1.06687 (7)0.0167 (3)
C60.28397 (12)0.35345 (13)1.00640 (7)0.0171 (3)
C70.09823 (13)0.37510 (14)0.83968 (7)0.0206 (3)
C80.86477 (12)0.13260 (14)1.05624 (7)0.0185 (3)
C91.00867 (12)0.09585 (15)1.13789 (7)0.0198 (3)
C101.12987 (14)0.06479 (16)1.20170 (8)0.0242 (3)
H20.37600.23140.79790.0271*
H30.64280.15340.90010.0187*
H50.46180.33091.13840.0247*
H60.19100.40601.03360.0199*
H70.10330.35590.76910.0267*
H8A0.89960.22401.01270.0191*
H8B0.82950.01991.02080.0222*
H101.22910.04291.25160.0372*
U11U22U33U12U13U23
O10.0204 (4)0.0323 (5)0.0256 (5)0.0041 (3)−0.0007 (3)−0.0039 (3)
O20.0168 (4)0.0228 (4)0.0150 (4)0.0031 (3)0.0020 (3)−0.0004 (3)
C10.0187 (5)0.0144 (5)0.0168 (5)−0.0028 (4)0.0016 (4)0.0003 (4)
C20.0219 (5)0.0178 (5)0.0149 (5)−0.0030 (4)0.0030 (4)−0.0011 (4)
C30.0194 (5)0.0172 (5)0.0169 (5)−0.0003 (4)0.0051 (4)−0.0014 (4)
C40.0174 (5)0.0134 (5)0.0162 (5)−0.0015 (4)0.0015 (4)0.0013 (4)
C50.0197 (5)0.0167 (5)0.0138 (5)−0.0015 (4)0.0034 (4)0.0004 (4)
C60.0177 (5)0.0158 (5)0.0180 (5)−0.0007 (4)0.0040 (4)−0.0003 (4)
C70.0214 (5)0.0203 (5)0.0182 (5)−0.0019 (4)−0.0004 (4)−0.0022 (4)
C80.0179 (5)0.0202 (5)0.0177 (5)0.0025 (4)0.0041 (4)−0.0002 (4)
C90.0196 (5)0.0207 (5)0.0199 (5)0.0007 (4)0.0060 (4)−0.0011 (4)
C100.0213 (5)0.0303 (6)0.0210 (5)0.0026 (5)0.0045 (4)−0.0001 (5)
O1—C71.2154 (14)C8—C91.4622 (13)
O2—C41.3659 (11)C9—C101.1897 (14)
O2—C81.4360 (13)C2—H20.970
C1—C21.3913 (16)C3—H30.968
C1—C61.4021 (15)C5—H50.995
C1—C71.4670 (14)C6—H60.977
C2—C31.3899 (14)C7—H71.010
C3—C41.3968 (15)C8—H8A0.988
C4—C51.3993 (15)C8—H8B0.980
C5—C61.3784 (13)C10—H100.950
O1···C62.8906 (13)C7···H8Biv3.4936
O2···C103.4132 (15)C7···H10iii2.9850
C1···C42.7763 (14)C8···H2viii3.5206
C2···C52.7778 (17)C8···H6xiii3.3423
C3···C62.8035 (17)C8···H8Avi3.4770
C3···C82.7953 (15)C8···H8Bvi3.0613
O1···O2i3.5839 (13)C9···H2viii2.9585
O1···C6ii3.3603 (15)C9···H3vi3.4464
O1···C8i3.5397 (16)C9···H6xiii3.2166
O1···C9i3.4739 (17)C9···H8Avi3.3479
O1···C10iii3.1575 (14)C9···H8Bvi2.9185
O2···O1i3.5839 (13)C10···H2viii3.0407
O2···C1i3.5034 (17)C10···H3vi2.9896
O2···C2iv3.5282 (16)C10···H3viii3.4607
O2···C6i3.5729 (15)C10···H5xiii3.5367
O2···C7i3.4779 (15)C10···H5xiv3.0372
C1···O2i3.5034 (17)C10···H6xiii3.5534
C1···C4i3.5512 (17)C10···H8Bvi3.2660
C1···C5i3.5660 (16)H2···O1xi3.5583
C1···C8iv3.5880 (18)H2···O2v2.9057
C2···O2iv3.5282 (16)H2···C7xi3.2950
C2···C5i3.5602 (17)H2···C8v3.5206
C2···C10v3.5491 (18)H2···C9v2.9585
C3···C4iv3.4949 (17)H2···C10v3.0407
C3···C5i3.5907 (18)H2···H5i3.5239
C3···C6i3.5640 (17)H2···H5v3.5908
C4···C1i3.5512 (17)H2···H7xi2.9435
C4···C3iv3.4949 (17)H2···H10v3.4275
C4···C6i3.3026 (16)H3···O1xiii3.4379
C5···C1i3.5660 (16)H3···C4iv3.5984
C5···C2i3.5602 (17)H3···C5iv3.5273
C5···C3i3.5907 (18)H3···C9vi3.4464
C6···O1ii3.3603 (15)H3···C10vi2.9896
C6···O2i3.5729 (15)H3···C10v3.4607
C6···C3i3.5640 (17)H3···H6i3.5598
C6···C4i3.3026 (16)H3···H7xi3.5107
C7···O2i3.4779 (15)H3···H10vi2.9257
C8···O1i3.5397 (16)H3···H10v3.2297
C8···C1iv3.5880 (18)H5···C1i3.5007
C8···C8vi3.5082 (17)H5···C2i3.3077
C8···C9vi3.5225 (17)H5···C3i3.5504
C9···O1i3.4739 (17)H5···C7viii3.1921
C9···C8vi3.5225 (17)H5···C10x3.5367
C10···O1vii3.1575 (14)H5···C10xii3.0372
C10···C2viii3.5491 (18)H5···H2i3.5239
O1···H62.6337H5···H2viii3.5908
O2···H32.6899H5···H7viii2.3799
O2···H52.4642H5···H10x3.4131
C1···H33.2914H5···H10xii2.8432
C1···H53.3209H6···O1ii2.4110
C2···H63.2988H6···O2i3.5493
C2···H72.5468H6···C3i3.5012
C3···H53.3126H6···C4i3.4439
C3···H8A2.7677H6···C7ii3.5637
C3···H8B2.6843H6···C8x3.3423
C4···H23.2789H6···C9x3.2166
C4···H63.2895H6···C10x3.5534
C4···H8A2.6337H6···H3i3.5598
C4···H8B2.5972H6···H6ii3.2783
C5···H33.3114H6···H8Ax2.6299
C6···H23.2855H6···H8Ai2.8648
C6···H73.3396H6···H8Biv3.2330
C7···H22.6135H6···H10xii3.1175
C7···H62.6767H7···O2v2.8373
C8···H32.5110H7···C2ix3.4881
C10···H8A3.1180H7···C4v3.4138
C10···H8B3.1119H7···C5v3.1133
H2···H32.3616H7···H2ix2.9435
H2···H72.3008H7···H3ix3.5107
H3···H8A2.3572H7···H5v2.3799
H3···H8B2.2315H7···H10iii3.0118
H5···H62.3967H8A···O1xiii2.7399
O1···H2ix3.5583H8A···O1i3.1014
O1···H3x3.4379H8A···C1xiii3.5673
O1···H6ii2.4110H8A···C6xiii3.2041
O1···H8Ax2.7399H8A···C6i3.4287
O1···H8Ai3.1014H8A···C7xiii3.3458
O1···H10iii2.2281H8A···C8vi3.4770
O2···H2viii2.9057H8A···C9vi3.3479
O2···H6i3.5493H8A···H6xiii2.6299
O2···H7viii2.8373H8A···H6i2.8648
C1···H5i3.5007H8A···H8Bvi2.9105
C1···H8Ax3.5673H8B···C1iv2.8875
C1···H8Biv2.8875H8B···C2iv3.2690
C2···H5i3.3077H8B···C5iv3.2946
C2···H7xi3.4881H8B···C6iv2.9001
C2···H8Biv3.2690H8B···C7iv3.4936
C3···H5i3.5504H8B···C8vi3.0613
C3···H6i3.5012H8B···C9vi2.9185
C4···H3iv3.5984H8B···C10vi3.2660
C4···H6i3.4439H8B···H6iv3.2330
C4···H7viii3.4138H8B···H8Avi2.9105
C5···H3iv3.5273H8B···H8Bvi2.8905
C5···H7viii3.1133H10···O1vii2.2281
C5···H8Biv3.2946H10···C5xiv3.5569
C5···H10xii3.5569H10···C7vii2.9850
C6···H8Ax3.2041H10···H2viii3.4275
C6···H8Ai3.4287H10···H3vi2.9257
C6···H8Biv2.9001H10···H3viii3.2297
C7···H2ix3.2950H10···H5xiii3.4131
C7···H5v3.1921H10···H5xiv2.8432
C7···H6ii3.5637H10···H6xiv3.1175
C7···H8Ax3.3458H10···H7vii3.0118
C4—O2—C8116.38 (8)C3—C2—H2120.247
C2—C1—C6119.71 (9)C2—C3—H3119.929
C2—C1—C7119.45 (9)C4—C3—H3121.483
C6—C1—C7120.82 (10)C4—C5—H5117.787
C1—C2—C3121.06 (10)C6—C5—H5122.175
C2—C3—C4118.59 (10)C1—C6—H6120.143
O2—C4—C3124.34 (10)C5—C6—H6120.002
O2—C4—C5114.89 (9)O1—C7—H7122.939
C3—C4—C5120.77 (9)C1—C7—H7112.094
C4—C5—C6120.02 (10)O2—C8—H8A109.216
C1—C6—C5119.85 (10)O2—C8—H8B109.121
O1—C7—C1124.97 (10)C9—C8—H8A109.879
O2—C8—C9108.48 (9)C9—C8—H8B109.452
C8—C9—C10177.37 (12)H8A—C8—H8B110.659
C1—C2—H2118.687C9—C10—H10177.936
C4—O2—C8—C9−177.31 (7)C7—C1—C6—C5−178.20 (9)
C8—O2—C4—C31.73 (13)C1—C2—C3—C4−0.28 (15)
C8—O2—C4—C5−177.84 (8)C2—C3—C4—O2−178.56 (9)
C2—C1—C6—C50.50 (15)C2—C3—C4—C50.99 (15)
C6—C1—C2—C3−0.46 (15)O2—C4—C5—C6178.63 (8)
C2—C1—C7—O1176.92 (10)C3—C4—C5—C6−0.96 (14)
C7—C1—C2—C3178.26 (9)C4—C5—C6—C10.20 (14)
C6—C1—C7—O1−4.38 (16)
D—H···AD—HH···AD···AD—H···A
C10—H10···O1vii0.952.233.1575 (14)166
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A D⋯A D—H⋯A
C10—H10⋯O1i 0.952.233.1575 (14)166

Symmetry code: (i) .

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