2-(4-Chloro­phen­yl)-1,3-dioxane – localization of hydrogen atoms

Hosten, E.C.; Betz, R.

doi:10.1107/S2414314625010466

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 10| Part 11| November 2025| x251046

https://doi.org/10.1107/S2414314625010466

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2-(4-Chlorophenyl)-1,3-dioxane – localization of hydrogen atoms

Eric Cyriel Hosten ^a and Richard Betz ^a ^*

^aNelson Mandela University, Summerstrand Campus, Department of Chemistry, University Way, Summerstrand, PO Box 77000, Port Elizabeth, 6031, South Africa
^*Correspondence e-mail: [email protected]

Edited by M. Bolte, Goethe-Universität Frankfurt, Germany (Received 14 November 2025; accepted 23 November 2025; online 28 November 2025)

The title compound, C₁₀H₁₁ClO₂, is an acetal-protected derivative of 4-chlorobenzaldehyde. The aliphatic ring adopts a chair conformation. In the crystal, weak C—H⋯O contacts connect the molecules into centrosymmetric dimers.

Keywords: crystal structure; C—H⋯O contacts.

CCDC reference: 2504999

Structure description

Aldehydes are one of the most important synthons in preparative organic chemistry on grounds of their versatile redox and nucleophilic properties that can be exploited for the synthesis of alcohols, carboxylic acids as well as a wide variety of additives such as, among others, sulfites and cyano- or chlorohydrines that, in their own right, are crucial building blocks for the synthesis of other target compounds (Becker et al., 2000 ). Owing to the reactivity of the CHO as well as the keto functional groups, protecting them during crucial reaction sequences in the wake of multi-step synthesis is of paramount importance. One common way to achieve this is by converting the carbonyl functionality to an acetal moiety by condensation with alcohols. Of particular interest are ring-type acetals derived from diols as these can give rise to interesting conformations of the resulting heterocycle. For cyclic acetals derived from benzladehyde, it might be interesting to elucidate whether the nature of substituents on the aromatic core might be able to determine the conformation of the dioxolane moiety. In this context, structural information about cyclic acetals with five-membered dioxolane rings derived from benzaldehyde derivatives bearing one halogen substituent in an ortho position (DeAngelis et al., 2008 ; Li et al., 2008 ; Liu et al., 2009 ) or para position (Bentabed-Ababsa et al., 2008 ; Gildenast et al., 2023 ; Wang et al., 2009 ; Bentabed-Ababsa et al., 2009 ; Toda et al., 2022 ; Yuan et al., 2017a ; Bhaumik et al., 2017 ) is available next to metrical parameters derived by diffraction studies based on single crystals for six-membered dioxolane rings derived from benzaldehyde derivatives bearing one halogen substituent in an ortho position [Imamoto et al., 1984 ; Laing et al., 1984 ; Wang et al., 2010 ; Sun et al., 2010 ; Guang-Chuan et al., 2019 ; Qiong et al., 2019 ; Mezo et al., 2021 ; Yuan et al., 2016a ,b , 2018 ; Brown et al., 1990 ; Ng et al., 2006 ; Li et al., 2016 ; Jia et al., 2012 , 2016a ; Ou et al., 2018 ; Warwicker, 1961 (no three-dimensional coordinates deposited)], meta position (Li et al., 2011 ; Ishihara et al., 2021 ) or para position (Hertung et al., 1981 ; Eliel et al., 1976 ; de Kok & Romers, 1970 ; Thuaud et al., 2016 ; Zhang et al., 2013 , 2014 , 2016 ; Benhamou et al., 2019 ; Scheffler & Mahrwald, 2012 ; Yuan et al., 2017b ; Zou et al., 2021 ; Jia et al., 2016b ; Janner et al., 2022 ; Xu et al., 2019 ). In continuation of our interest in the structural chemistry of acetals (Betz & Klüfers, 2007a ,b ,c ; Betz & Klüfers, 2008 ; Betz et al., 2007a ,b ,c ,d ), we synthesized the title compound and determined its molecular and crystal structure. Although the latter has been reported previously (de Kok & Romers, 1970; CSD ref code: CPDIOX), no hydrogen atoms were taken into account during the refinement, thus precluding the possibility to analyse the intra- and intermolecular contacts. This study is intended to close this gap.

The structure solution shows the presence of the 1,3-propanediol derived cyclic acetal of 4-chlorobenzaldehyde. C—O bond lengths and angles are found in good agreement with other cyclic acetals whose metrical parameters have been deposited with the Cambridge Structural Database (Groom et al., 2016 ). A conformational analysis (Cremer & Pople, 1975 ) of the 1,3-dioxolane ring shows the latter to adopt a ⁴C₁ (^C4C_O1) conformation (Boeyens, 1978 ). The least-squares planes as defined by the non-hydrogen atoms of the aromatic moiety on the one hand and the oxolane moiety on the other hand intersect at an angle of 18.35 (7)° only (Fig. 1).

Figure 1
The molecular structure of the title compound, with atom labels and anisotropic displacement ellipsoids (drawn at 50% probability level).

In the crystal, only weak C—H⋯O contacts are observed whose range falls by 0.06 Å below the sum of van-der Waals radii of the atoms participating in them. These are established between one of the hydrogen atoms in an ortho position to the chlorine atom on the aromatic moiety as donor and one of the intracyclic oxygen atoms as acceptor, giving rise to centrosymmetric dimers (Fig. 2, Table 1). In terms of graph-set analysis, (Etter et al., 1990 ; Bernstein et al., 1995 ) these contacts require a R₂²(12) descriptor on the unary level. While π-stacking is not a prominent stabilizing feature with the shortest intercentroid distance between two centres of gravity measured at 4.7025 (8) Å (the length of the crystallographic a axis), a C—H⋯π contact is present that is supported by the hydrogen atom of the methine group. Furthermore, a C—Cl⋯π contact is apparent. Although the latter exhibits an angle of 90.78 (5)° (far away from linearity), it has been found that this does not significantly weaken the force of such an interaction (Imai et al., 2008 ). Both interactions involving the aromatic system result in connecting the molecules to chains along the crystallographic a-axis direction (Fig. 3, Table 1).

Table 1
Hydrogen-bond geometry (Å, °)

C_g(1) is the centroid of carbon atoms C11–C16.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O2ⁱ	0.95	2.66	3.4686 (16)	143
C1—H1⋯C_g(1)ⁱⁱ	1.00	2.58	3.5282 (15)	158
C14—Cl1⋯C_g(1)ⁱⁱⁱ	1.74 (1)	3.49 (1)	3.9197 (15)	91 (1)
Symmetry codes: (i) ; (ii) ; (iii) .

Figure 2
Intermolecular contacts, viewed along [100].

Figure 3
Intermolecular C—H⋯π contacts, viewed along [010].

Synthesis and crystallization

The compound was prepared following a standard procedure by reacting para-chlorobenzaldehyde with 1,3-propanediol (Dong et al., 2018 ). Crystals suitable for the diffraction study were obtained upon storing the isolated product at ambient conditions.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₀H₁₁ClO₂
M_r	198.64
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	200
a, b, c (Å)	4.7025 (1), 9.6336 (3), 10.8933 (3)
α, β, γ (°)	102.9908 (9), 90.6153 (10), 103.538 (1)
V (Å³)	466.45 (2)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.37
Crystal size (mm)	0.38 × 0.14 × 0.05

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Numerical (SADABS; Krause et al., 2015 )
T_min, T_max	0.919, 0.996
No. of measured, independent and observed [I > 2σ(I)] reflections	31279, 2315, 2069
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.084, 1.08
No. of reflections	2315
No. of parameters	119
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.21
Computer programs: APEX2 and SAINT (Bruker, 2014 ), SHELXS97 (Sheldrick 2008 ), ORTEP-3 for Windows (Farrugia, 2012 ), Mercury (Macrae et al., 2008 ), SHELXL2019/3 (Sheldrick, 2015 ) and PLATON (Spek, 2020 ).

Structural data

CCDC reference: 2504999

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314625010466/bt4190sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314625010466/bt4190Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314625010466/bt4190Isup3.cml

checkCIF report

Computing details top

2-(4-Chlorophenyl)-1,3-dioxane top

Crystal data top

C₁₀H₁₁ClO₂	Z = 2
M_r = 198.64	F(000) = 208
Triclinic, P1	D_x = 1.414 Mg m⁻³
a = 4.7025 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.6336 (3) Å	Cell parameters from 9212 reflections
c = 10.8933 (3) Å	θ = 2.2–28.3°
α = 102.9908 (9)°	µ = 0.37 mm⁻¹
β = 90.6153 (10)°	T = 200 K
γ = 103.538 (1)°	Rod, colourless
V = 466.45 (2) Å³	0.38 × 0.14 × 0.05 mm

Data collection top

Bruker APEXII CCD diffractometer	2069 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.027
Absorption correction: numerical (SADABS; Krause et al., 2015)	θ_max = 28.3°, θ_min = 2.2°
T_min = 0.919, T_max = 0.996	h = −6→6
31279 measured reflections	k = −12→12
2315 independent reflections	l = −14→14

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)] = 0.032	H-atom parameters constrained
wR(F²) = 0.084	w = 1/[σ²(F_o²) + (0.0328P)² + 0.2109P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max = 0.001
2315 reflections	Δρ_max = 0.40 e Å⁻³
119 parameters	Δρ_min = −0.21 e Å⁻³
0 restraints	Extinction correction: SHELXL2019/2 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.009 (3)

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. The carbon-bound H atoms were placed in calculated positions (C–H 0.95 Å for aromatic carbon atoms, C–H 0.99 Å for the methylene groups, C–H 1.00 Å for the methine group) and were included in the refinement in the riding model approximation, with U(H) set to 1.2U_eq(C).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.71337 (8)	0.09478 (4)	0.16147 (3)	0.03644 (12)
O1	0.1662 (2)	0.66451 (11)	0.39209 (8)	0.0344 (2)
O2	0.1908 (2)	0.67841 (10)	0.18198 (9)	0.0312 (2)
C1	0.0987 (3)	0.58707 (13)	0.26568 (11)	0.0228 (2)
H1	−0.117911	0.545491	0.251496	0.027*
C11	0.2512 (3)	0.46337 (13)	0.23963 (11)	0.0222 (2)
C12	0.3153 (3)	0.40527 (14)	0.11735 (11)	0.0261 (3)
H12	0.261482	0.443755	0.049967	0.031*
C13	0.4571 (3)	0.29161 (14)	0.09245 (12)	0.0278 (3)
H13	0.501563	0.252535	0.008795	0.033*
C14	0.5326 (3)	0.23623 (13)	0.19160 (12)	0.0251 (2)
C15	0.4683 (3)	0.29100 (14)	0.31383 (12)	0.0285 (3)
H15	0.520747	0.251661	0.380890	0.034*
C16	0.3257 (3)	0.40451 (14)	0.33715 (11)	0.0264 (3)
H16	0.278748	0.442234	0.420707	0.032*
C2	0.0114 (4)	0.77863 (17)	0.42187 (14)	0.0410 (4)
H2A	0.061919	0.833436	0.510809	0.049*
H2B	−0.202458	0.734805	0.411623	0.049*
C3	0.0936 (4)	0.88251 (16)	0.33514 (15)	0.0397 (3)
H3A	−0.025577	0.956148	0.350172	0.048*
H3B	0.303009	0.934975	0.351864	0.048*
C4	0.0379 (4)	0.79369 (16)	0.20015 (13)	0.0362 (3)
H4A	−0.175037	0.750684	0.180963	0.043*
H4B	0.106251	0.858277	0.141982	0.043*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0357 (2)	0.03054 (18)	0.0467 (2)	0.01563 (14)	0.00267 (14)	0.00859 (14)
O1	0.0519 (6)	0.0352 (5)	0.0206 (4)	0.0236 (5)	−0.0002 (4)	0.0023 (4)
O2	0.0418 (5)	0.0319 (5)	0.0283 (5)	0.0185 (4)	0.0123 (4)	0.0139 (4)
C1	0.0233 (6)	0.0251 (6)	0.0199 (5)	0.0056 (4)	0.0021 (4)	0.0055 (4)
C11	0.0201 (5)	0.0236 (5)	0.0223 (6)	0.0040 (4)	0.0012 (4)	0.0057 (4)
C12	0.0292 (6)	0.0303 (6)	0.0210 (6)	0.0097 (5)	0.0015 (5)	0.0077 (5)
C13	0.0299 (6)	0.0307 (6)	0.0233 (6)	0.0102 (5)	0.0028 (5)	0.0045 (5)
C14	0.0209 (6)	0.0230 (5)	0.0314 (6)	0.0058 (4)	0.0004 (5)	0.0059 (5)
C15	0.0310 (7)	0.0301 (6)	0.0271 (6)	0.0084 (5)	0.0000 (5)	0.0114 (5)
C16	0.0299 (6)	0.0288 (6)	0.0210 (6)	0.0071 (5)	0.0024 (5)	0.0070 (5)
C2	0.0614 (10)	0.0412 (8)	0.0269 (7)	0.0300 (7)	0.0065 (6)	0.0030 (6)
C3	0.0503 (9)	0.0292 (7)	0.0413 (8)	0.0169 (6)	0.0014 (7)	0.0043 (6)
C4	0.0496 (9)	0.0356 (7)	0.0329 (7)	0.0233 (6)	0.0081 (6)	0.0137 (6)

Geometric parameters (Å, º) top

Cl1—C14	1.7419 (12)	C14—C15	1.3821 (18)
O1—C1	1.4041 (14)	C15—C16	1.3898 (18)
O1—C2	1.4363 (16)	C15—H15	0.9500
O2—C1	1.4085 (14)	C16—H16	0.9500
O2—C4	1.4380 (15)	C2—C3	1.515 (2)
C1—C11	1.5056 (16)	C2—H2A	0.9900
C1—H1	1.0000	C2—H2B	0.9900
C11—C16	1.3888 (16)	C3—C4	1.511 (2)
C11—C12	1.3896 (17)	C3—H3A	0.9900
C12—C13	1.3891 (17)	C3—H3B	0.9900
C12—H12	0.9500	C4—H4A	0.9900
C13—C14	1.3844 (18)	C4—H4B	0.9900
C13—H13	0.9500

C1—O1—C2	110.20 (10)	C16—C15—H15	120.5
C1—O2—C4	110.26 (10)	C11—C16—C15	120.71 (11)
O1—C1—O2	111.52 (10)	C11—C16—H16	119.6
O1—C1—C11	108.82 (9)	C15—C16—H16	119.6
O2—C1—C11	108.88 (9)	O1—C2—C3	109.75 (12)
O1—C1—H1	109.2	O1—C2—H2A	109.7
O2—C1—H1	109.2	C3—C2—H2A	109.7
C11—C1—H1	109.2	O1—C2—H2B	109.7
C16—C11—C12	119.17 (11)	C3—C2—H2B	109.7
C16—C11—C1	120.46 (11)	H2A—C2—H2B	108.2
C12—C11—C1	120.36 (11)	C4—C3—C2	108.41 (12)
C13—C12—C11	120.79 (11)	C4—C3—H3A	110.0
C13—C12—H12	119.6	C2—C3—H3A	110.0
C11—C12—H12	119.6	C4—C3—H3B	110.0
C14—C13—C12	118.88 (11)	C2—C3—H3B	110.0
C14—C13—H13	120.6	H3A—C3—H3B	108.4
C12—C13—H13	120.6	O2—C4—C3	109.75 (11)
C15—C14—C13	121.42 (12)	O2—C4—H4A	109.7
C15—C14—Cl1	119.38 (10)	C3—C4—H4A	109.7
C13—C14—Cl1	119.20 (10)	O2—C4—H4B	109.7
C14—C15—C16	119.00 (11)	C3—C4—H4B	109.7
C14—C15—H15	120.5	H4A—C4—H4B	108.2

C2—O1—C1—O2	62.93 (14)	C12—C13—C14—C15	0.4 (2)
C2—O1—C1—C11	−176.94 (11)	C12—C13—C14—Cl1	−179.44 (10)
C4—O2—C1—O1	−62.80 (13)	C13—C14—C15—C16	−0.2 (2)
C4—O2—C1—C11	177.11 (10)	Cl1—C14—C15—C16	179.59 (10)
O1—C1—C11—C16	25.22 (15)	C12—C11—C16—C15	1.37 (19)
O2—C1—C11—C16	146.96 (11)	C1—C11—C16—C15	−179.55 (11)
O1—C1—C11—C12	−155.71 (11)	C14—C15—C16—C11	−0.64 (19)
O2—C1—C11—C12	−33.96 (15)	C1—O1—C2—C3	−58.71 (16)
C16—C11—C12—C13	−1.22 (19)	O1—C2—C3—C4	54.64 (17)
C1—C11—C12—C13	179.70 (11)	C1—O2—C4—C3	58.44 (15)
C11—C12—C13—C14	0.35 (19)	C2—C3—C4—O2	−54.49 (17)

Hydrogen-bond geometry (Å, º) top

C_g(1) is the centroid of carbon atoms C11–C16.

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O2ⁱ	0.95	2.66	3.4686 (16)	143
C1—H1···C_g(1)ⁱⁱ	1.00	2.58	3.5282 (15)	158
C14—Cl1···C_g(1)ⁱⁱⁱ	1.74 (1)	3.49 (1)	3.9197 (15)	91 (1)

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

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

2-(4-Chloro­phen­yl)-1,3-dioxane – localization of hydrogen atoms

Structure description

Synthesis and crystallization

Refinement

Structural data

References

organic compounds

2-(4-Chlorophenyl)-1,3-dioxane – localization of hydrogen atoms