Crystal structures of dimethyl 5-iodo­iso­phthal­ate and dimethyl 5-ethynyl­iso­phthal­ate

Hauptvogel, I.; Seichter, W.; Weber, E.

doi:10.1107/S205698901800912X

research communications

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 74| Part 8| August 2018| Pages 1093-1096

https://doi.org/10.1107/S205698901800912X

Open

access

Crystal structures of dimethyl 5-iodoisophthalate and dimethyl 5-ethynylisophthalate

Ines Hauptvogel,^a Wilhelm Seichter ^a and Edwin Weber ^a ^*

^aTU Bergakademie Freiberg, Leipziger Str. 29, D-09596 Freiberg/Sachsen, Germany
^*Correspondence e-mail: edwin.weber@chemie.tu-freiberg.de

Edited by M. Zeller, Purdue University, USA (Received 29 May 2018; accepted 22 June 2018; online 13 July 2018)

In dimethyl 5-iodoisophthalate, C₁₀H₉IO₄, (I), the planes through the methyl carboxylate moieties are tilted with respect to the benzene ring, whereas the molecular framework of dimethyl 5-ethynylisophthalate, C₁₂H₁₀O₄, (II), is perfectly planar. The crystal structure of (I) is stabilized by a three-dimensional supramolecular network comprising C—H⋯O=C hydrogen bonds, as well as I⋯O=C interactions. In the crystal of (II), the molecules are connected via C—H_ethynyl⋯O=C hydrogen bonds to infinite strands. Moreover, π–π arene stacking interactions connect the molecular chains into two-dimensional supramolecular aggregates.

Keywords: crystal structure; 5-substituted dimethyl isophthalates; I⋯O=C interaction; C—H⋯O and C—H⋯I hydrogen bonding; π–π stacking.

CCDC references: 780476; 780475

1. Chemical context

In recent years, the design of solid porous framework materials (MacGillivray, 2010 ; Furukawa et al., 2013 ; Eddaoudi et al., 2015 ) has become a very important topic in the field of supramolecular crystal engineering (Desiraju et al., 2011 ). Associated with it, so-called linker molecules featuring a geometrically rigid structure frequently being of linear, trigonal or tetrahedral shape and having carboxylic acid functions as terminal groups play a key role in building such systems (Lin et al., 2006 ; Hausdorf et al., 2009 ; Zheng et al., 2010 ). In the course of the synthesis of the respective linkers, the title compounds (I) and (II), both being 5-substituted dimethyl isophthalates, are much used intermediates. However, these compounds are not only synthetically significant but also show interesting structures in the crystalline state, as demonstrated herein.

2. Structural commentary

The molecular structures of the title compounds, (I) and (II), are illustrated in Fig. 1a and 1b, respectively. Taking into account experimental error, the bond distances within the isophthalate framework agree well with those found in the crystal structure of dimethyl isophthalate (Gallagher, 2012 ). Compound (I) crystallizes in the orthorhombic space group Pna2₁ with one molecule in the asymmetric unit. The molecule adopts a twisted conformation with the mean planes defined by the methyl carboxylate moieties inclined at angles of 12.6 (2) and 6.0 (2)° with respect to the plane of the benzene ring. Compound (II) crystallizes in the orthorhombic space group Pnma with the molecule located on a symmetry plane, i.e. the molecule is perfectly planar. However, the molecule adopts approximate C_2v symmetry with the atoms C2, C5, C11 and C12 lying on a non-crystallographic bisecting symmetry plane.

Figure 1
Perspective view of the molecular structures of the title compounds, (a) (I)

and (b) (II)

, with atom labelling. Anisotropic displacement ellipsoids are drawn at the 40% probability level.

3. Supramolecular features

Infinite strands with the molecules connected via I⋯O=C interactions [I1⋯O3—C9(x − $[1\over2]$ , y + $[3\over2]$ , z − 1; D⋯A = 3.129 (2) (Desiraju & Steiner, 1999 ) (Politzer et al. 2007 ; Desiraju et al., 2013 ), represent the basic supramolecular aggregates of the crystal structure of (I). Association of the molecular strands by C—H⋯O=C type hydrogen bonds (Table 1) (Desiraju & Steiner, 1999) and π–π stacking interactions [centroid–centroid distance = 4.149 (2) Å] (Tiekink & Zukerman-Schpector, 2012 ) generate a three-dimensional supramolecular network (Fig. 2). In the crystal structure of (II), the molecules are connected via C_ethynyl—H⋯O=C bonds (Table 2) into infinite strands, which are further arranged into molecular sheets that extend parallel to the ac plane (Fig. 3). Furthermore, π–π arene interactions with a centroid–centroid distance of 3.566 (1) Å and a slippage of 1.325 Å between the interacting aromatic rings stabilize the crystal structure along the stacking axis of the molecular sheets.

Table 1
Hydrogen-bond geometry (Å, °) for (I)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8A⋯O1ⁱ	0.98	2.55	3.257 (4)	129
Symmetry code: (i) $[-x+1, -y+1, z-{\script{1\over 2}}]$ .

Table 2
Hydrogen-bond geometry (Å, °) for (II)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O1ⁱ	0.94	2.29	3.223 (1)	172
Symmetry code: (i) x-1, y, z.

Figure 2
Packing diagram of compound (I)

viewed down the a axis. Dashed lines represent hydrogen-bonding interactions.

Figure 3
Packing excerpt of compound (II)

viewed down the b axis. Dashed lines represent hydrogen-bonding interactions.

4. Database survey

The search in the Cambridge Structural Database (CSD, Version 5.38, update May 2017; Groom et al., 2016 ) for meta-substituted derivatives of dimethyl isophthalate excluding their metal complexes, solvates and salts gave 18 hits. None of these compounds represents a 5-halogen- and 5-alkynyl-substituted dimethyl isophalate. The parent compound, dimethyl isophthalate (CSD refcode GOHRUS; Gallagher & Mocilac, 2012) crystallizes in space group Pna2₁ with two conformationally similar molecules in the asymmetric unit. The independent molecules participate in different ways in non-covalent bonding. One of them is involved in the formation of linear strands with the molecules connected by C—H_aryl⋯O=C bonds. Interstrand association is accomplished by π–π arene stacking. Molecules related by the twofold screw axis are also linked via C—H_aryl⋯O=C bonding to form helical strands. In addition, these strands are stabilized by π–π stacking forces.

5. Synthesis and crystallization

Compounds (I) and (II) were synthesized following literature procedures. This involves a diazotization/iodination reaction of dimethyl 5-aminoisophthalate (Mazik & König, 2006 ) to give compound (I). Subsequent reaction of (I) with 2-methylbut-3-yne-2-ol (MEBYNOL) using a Pd-catalysed Sonogashira coupling procedure (Doucet & Hierso, 2007 ; Rafael & Carmen, 2007 ) yielded the corresponding blocked acetylenic diester as an intermediate (Hauptvogel et al., 2011 ). Removal of the 2-hydroxypropyl blocking group was undertaken using sodium hydride in toluene and quenching with water to result in the title compound (II) (Havens & Hergenrother, 1985 ; Hauptvogel et al., 2011).

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. Hydrogen atoms were positioned geometrically and refined using a riding model with C—H distances of 0.94–0.98 Å and U_iso(H) = 1.5U_eq(C-methyl) or U_iso(H) = 1.2U_eq(C) for other H atoms.

Table 3
Experimental details

	(I)	(II)
Crystal data
Chemical formula	C₁₀H₉IO₄	C₁₂H₁₀O₄
M_r	320.07	218.20
Crystal system, space group	Orthorhombic, Pna2₁	Orthorhombic, Pnma
Temperature (K)	143	223
a, b, c (Å)	7.7483 (2), 19.3451 (6), 7.2338 (2)	10.1206 (5), 6.6219 (4), 16.3658 (8)
V (Å³)	1084.29 (5)	1096.80 (10)
Z	4	4
Radiation type	Mo Kα	Mo Kα
μ (mm⁻¹)	2.94	0.10
Crystal size (mm)	0.30 × 0.22 × 0.15	0.54 × 0.12 × 0.10

Data collection
Diffractometer	Bruker APEXII CCD area detector	Bruker APEXII CCD area detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 2008a )	Multi-scan (SADABS; Sheldrick, 2008a)
T_min, T_max	0.472, 0.666	0.948, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	22794, 2909, 2806	12397, 1292, 932
R_int	0.026	0.033
(sin θ/λ)_max (Å⁻¹)	0.684	0.638

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.015, 0.038, 1.05	0.039, 0.110, 1.03
No. of reflections	2909	1292
No. of parameters	139	87
No. of restraints	1	0
H-atom treatment	H-atom parameters constrained	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.44	0.17, −0.18
Absolute structure	Flack x determined using 1255 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013 )	–
Absolute structure parameter	−0.004 (8)	–
Computer programs: APEX2 and SAINT (Bruker, 2014 ), SHELXT (Sheldrick, 2015a ), SHELXL2018 (Sheldrick, 2015b ), ORTEP-3 for Windows (Farrugia, 2012 ) and SHELXTL (Sheldrick, 2008b ).

Supporting information

CCDC references: 780476; 780475

Crystal structure: contains datablocks I, II, global. DOI: https://doi.org/10.1107/S205698901800912X/zl2732sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S205698901800912X/zl2732Isup4.hkl

Structure factors: contains datablock II. DOI: https://doi.org/10.1107/S205698901800912X/zl2732IIsup5.hkl

Supporting information file. DOI: https://doi.org/10.1107/S205698901800912X/zl2732Isup4.cml

Supporting information file. DOI: https://doi.org/10.1107/S205698901800912X/zl2732IIsup5.cml

checkCIF report

Computing details top

For both structures, data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXT (Sheldrick, 2015a). Program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b) for (I); SHELXL2014 (Sheldrick, 2015b) for (II). For both structures, molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008b).

1,3-Dimethyl 1-iodocyclohexa-3,5-diene-1,3-dicarboxylate (I) top

Crystal data top

C₁₀H₉IO₄	D_x = 1.961 Mg m⁻³
M_r = 320.07	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna2₁	Cell parameters from 5755 reflections
a = 7.7483 (2) Å	θ = 3.0–33.7°
b = 19.3451 (6) Å	µ = 2.94 mm⁻¹
c = 7.2338 (2) Å	T = 143 K
V = 1084.29 (5) Å³	Irregular, colourless
Z = 4	0.30 × 0.22 × 0.15 mm
F(000) = 616

Data collection top

Bruker APEXII CCD area detector diffractometer	2806 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.026
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a)	θ_max = 29.1°, θ_min = 1.1°
T_min = 0.472, T_max = 0.666	h = −10→10
22794 measured reflections	k = −26→26
2909 independent reflections	l = −9→9

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.015	w = 1/[σ²(F_o²) + (0.019P)² + 0.3689P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.038	(Δ/σ)_max = 0.002
S = 1.05	Δρ_max = 0.47 e Å⁻³
2909 reflections	Δρ_min = −0.44 e Å⁻³
139 parameters	Absolute structure: Flack x determined using 1255 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
1 restraint	Absolute structure parameter: −0.004 (8)

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. Refined as a 2-component twin.

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

	x	y	z	U_iso*/U_eq
I1	0.81504 (2)	0.66115 (2)	0.83115 (6)	0.02386 (5)
O1	0.5202 (3)	0.54751 (11)	0.1864 (3)	0.0327 (5)
O2	0.3831 (3)	0.63417 (11)	0.0411 (3)	0.0260 (4)
O3	0.4971 (3)	0.87789 (10)	0.2029 (3)	0.0281 (5)
O4	0.6557 (3)	0.89701 (11)	0.4576 (3)	0.0282 (5)
C1	0.5514 (4)	0.66267 (12)	0.2993 (4)	0.0190 (8)
C2	0.5347 (3)	0.73272 (14)	0.2585 (4)	0.0198 (5)
H2	0.479369	0.746965	0.147720	0.024*
C3	0.5994 (3)	0.78152 (14)	0.3805 (3)	0.0194 (5)
C4	0.6796 (3)	0.76086 (15)	0.5445 (4)	0.0206 (5)
H4	0.723931	0.794439	0.627770	0.025*
C5	0.6940 (3)	0.69088 (15)	0.5850 (4)	0.0207 (5)
C6	0.6295 (4)	0.64128 (15)	0.4637 (4)	0.0209 (5)
H6	0.638485	0.593502	0.492478	0.025*
C7	0.4856 (4)	0.60819 (14)	0.1721 (4)	0.0223 (5)
C8	0.3221 (5)	0.58545 (18)	−0.0951 (5)	0.0330 (7)
H8A	0.418544	0.571014	−0.173823	0.049*
H8B	0.232932	0.607288	−0.171341	0.049*
H8C	0.273509	0.544937	−0.032593	0.049*
C9	0.5768 (3)	0.85636 (11)	0.3323 (8)	0.0214 (4)
C10	0.6363 (5)	0.97101 (16)	0.4293 (5)	0.0338 (7)
H10A	0.688803	0.984036	0.311034	0.051*
H10B	0.693716	0.995947	0.529896	0.051*
H10C	0.513396	0.982919	0.427800	0.051*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.02804 (8)	0.02336 (8)	0.02019 (8)	−0.00006 (6)	−0.00121 (12)	0.00381 (11)
O1	0.0500 (14)	0.0174 (10)	0.0308 (12)	0.0032 (9)	−0.0060 (10)	−0.0006 (9)
O2	0.0300 (11)	0.0187 (10)	0.0293 (11)	0.0017 (8)	−0.0066 (9)	−0.0048 (8)
O3	0.0347 (12)	0.0194 (10)	0.0301 (11)	0.0027 (9)	−0.0082 (9)	0.0019 (8)
O4	0.0382 (12)	0.0165 (9)	0.0299 (11)	−0.0011 (8)	−0.0073 (9)	−0.0004 (9)
C1	0.0216 (11)	0.0183 (10)	0.017 (2)	0.0009 (9)	0.0020 (10)	−0.0004 (9)
C2	0.0196 (12)	0.0190 (12)	0.0209 (11)	0.0022 (10)	0.0042 (10)	0.0019 (10)
C3	0.0191 (11)	0.0183 (11)	0.0208 (13)	0.0013 (9)	0.0025 (9)	0.0012 (8)
C4	0.0217 (13)	0.0191 (13)	0.0211 (12)	−0.0014 (10)	0.0017 (10)	−0.0012 (10)
C5	0.0224 (13)	0.0217 (13)	0.0181 (12)	0.0022 (10)	0.0023 (10)	0.0017 (10)
C6	0.0242 (13)	0.0183 (12)	0.0201 (12)	0.0016 (10)	0.0024 (11)	0.0013 (10)
C7	0.0256 (13)	0.0197 (12)	0.0217 (13)	−0.0011 (10)	0.0035 (11)	−0.0011 (10)
C8	0.0409 (19)	0.0257 (15)	0.0323 (15)	0.0005 (13)	−0.0088 (13)	−0.0075 (13)
C9	0.0218 (10)	0.0173 (9)	0.0250 (10)	−0.0001 (8)	0.0096 (18)	−0.002 (2)
C10	0.0453 (19)	0.0174 (14)	0.0387 (19)	0.0014 (13)	−0.0064 (15)	−0.0021 (12)

Geometric parameters (Å, º) top

I1—C5	2.093 (3)	C3—C4	1.398 (4)
O1—C7	1.209 (3)	C3—C9	1.499 (4)
O2—C7	1.335 (4)	C4—C5	1.390 (4)
O2—C8	1.443 (4)	C4—H4	0.9500
O3—C9	1.196 (5)	C5—C6	1.393 (4)
O4—C9	1.347 (5)	C6—H6	0.9500
O4—C10	1.454 (4)	C8—H8A	0.9800
C1—C2	1.393 (3)	C8—H8B	0.9800
C1—C6	1.398 (4)	C8—H8C	0.9800
C1—C7	1.489 (4)	C10—H10A	0.9800
C2—C3	1.386 (4)	C10—H10B	0.9800
C2—H2	0.9500	C10—H10C	0.9800

C7—O2—C8	115.7 (2)	C1—C6—H6	120.4
C9—O4—C10	115.7 (3)	O1—C7—O2	124.0 (3)
C2—C1—C6	120.5 (3)	O1—C7—C1	124.0 (3)
C2—C1—C7	121.8 (3)	O2—C7—C1	112.1 (2)
C6—C1—C7	117.7 (2)	O2—C8—H8A	109.5
C3—C2—C1	119.7 (3)	O2—C8—H8B	109.5
C3—C2—H2	120.2	H8A—C8—H8B	109.5
C1—C2—H2	120.2	O2—C8—H8C	109.5
C2—C3—C4	120.4 (3)	H8A—C8—H8C	109.5
C2—C3—C9	117.9 (3)	H8B—C8—H8C	109.5
C4—C3—C9	121.7 (3)	O3—C9—O4	123.9 (2)
C5—C4—C3	119.5 (3)	O3—C9—C3	125.3 (3)
C5—C4—H4	120.2	O4—C9—C3	110.7 (3)
C3—C4—H4	120.2	O4—C10—H10A	109.5
C4—C5—C6	120.6 (3)	O4—C10—H10B	109.5
C4—C5—I1	118.9 (2)	H10A—C10—H10B	109.5
C6—C5—I1	120.5 (2)	O4—C10—H10C	109.5
C5—C6—C1	119.2 (3)	H10A—C10—H10C	109.5
C5—C6—H6	120.4	H10B—C10—H10C	109.5

C6—C1—C2—C3	1.3 (4)	C8—O2—C7—O1	−4.1 (4)
C7—C1—C2—C3	−179.4 (2)	C8—O2—C7—C1	176.3 (3)
C1—C2—C3—C4	−0.6 (4)	C2—C1—C7—O1	168.0 (3)
C1—C2—C3—C9	−179.3 (3)	C6—C1—C7—O1	−12.7 (4)
C2—C3—C4—C5	−0.1 (4)	C2—C1—C7—O2	−12.5 (4)
C9—C3—C4—C5	178.5 (3)	C6—C1—C7—O2	166.8 (3)
C3—C4—C5—C6	0.1 (4)	C10—O4—C9—O3	1.1 (5)
C3—C4—C5—I1	179.86 (19)	C10—O4—C9—C3	−177.5 (3)
C4—C5—C6—C1	0.7 (4)	C2—C3—C9—O3	5.3 (5)
I1—C5—C6—C1	−179.1 (2)	C4—C3—C9—O3	−173.3 (3)
C2—C1—C6—C5	−1.3 (4)	C2—C3—C9—O4	−176.1 (3)
C7—C1—C6—C5	179.4 (2)	C4—C3—C9—O4	5.3 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O1ⁱ	0.98	2.55	3.257 (4)	129

Symmetry code: (i) −x+1, −y+1, z−1/2.

1,3-Dimethyl 1-ethynylcyclohexa-3,5-diene-1,3-dicarboxylate (II) top

Crystal data top

C₁₂H₁₀O₄	D_x = 1.321 Mg m⁻³
M_r = 218.20	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pnma	Cell parameters from 2950 reflections
a = 10.1206 (5) Å	θ = 2.4–23.1°
b = 6.6219 (4) Å	µ = 0.10 mm⁻¹
c = 16.3658 (8) Å	T = 223 K
V = 1096.80 (10) Å³	Column, colourless
Z = 4	0.54 × 0.12 × 0.10 mm
F(000) = 456

Data collection top

Bruker APEXII CCD area detector diffractometer	932 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.033
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a)	θ_max = 27.0°, θ_min = 2.5°
T_min = 0.948, T_max = 0.990	h = −12→12
12397 measured reflections	k = −8→5
1292 independent reflections	l = −20→19

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.039	H-atom parameters constrained
wR(F²) = 0.110	w = 1/[σ²(F_o²) + (0.0486P)² + 0.2932P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
1292 reflections	Δρ_max = 0.17 e Å⁻³
87 parameters	Δρ_min = −0.18 e Å⁻³

Special details top

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	1.25864 (13)	0.2500	0.40733 (10)	0.0552 (4)
O2	1.08848 (14)	0.2500	0.32081 (9)	0.0519 (4)
O3	1.15356 (16)	0.2500	0.70802 (10)	0.0759 (6)
O4	0.94247 (15)	0.2500	0.74402 (9)	0.0617 (5)
C1	0.98919 (18)	0.2500	0.60451 (11)	0.0339 (4)
C2	1.08100 (18)	0.2500	0.54143 (12)	0.0350 (4)
H2	1.1718	0.2500	0.5536	0.042*
C3	1.03958 (18)	0.2500	0.46063 (12)	0.0339 (4)
C4	0.90505 (19)	0.2500	0.44325 (12)	0.0361 (4)
H4	0.8767	0.2500	0.3886	0.043*
C5	0.81192 (17)	0.2500	0.50582 (12)	0.0348 (4)
C6	0.85496 (18)	0.2500	0.58682 (12)	0.0340 (4)
H6	0.7929	0.2500	0.6296	0.041*
C7	1.0392 (2)	0.2500	0.68995 (13)	0.0428 (5)
C8	0.9818 (3)	0.2500	0.82935 (14)	0.0791 (9)
H8A	1.0203	0.1202	0.8431	0.119*	0.5
H8B	0.9050	0.2740	0.8634	0.119*	0.5
H8C	1.0465	0.3558	0.8385	0.119*	0.5
C9	1.1418	0.2500	0.3949	0.039
C10	1.1813	0.2500	0.2530	0.067
H10A	1.1353	0.2149	0.2030	0.101*	0.5
H10B	1.2505	0.1519	0.2633	0.101*	0.5
H10C	1.2202	0.3832	0.2474	0.101*	0.5
C11	0.67260 (19)	0.2500	0.48649 (12)	0.0406 (5)
C12	0.5604 (2)	0.2500	0.47022 (14)	0.0532 (6)
H12	0.4700	0.2500	0.4571	0.064*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0293 (8)	0.0828 (11)	0.0536 (10)	0.000	0.0049 (7)	0.000
O2	0.0409 (9)	0.0783 (11)	0.0364 (8)	0.000	0.0066 (7)	0.000
O3	0.0329 (9)	0.1475 (18)	0.0473 (10)	0.000	−0.0079 (8)	0.000
O4	0.0362 (9)	0.1153 (14)	0.0336 (8)	0.000	−0.0026 (7)	0.000
C1	0.0294 (10)	0.0371 (10)	0.0352 (11)	0.000	−0.0006 (8)	0.000
C2	0.0257 (9)	0.0385 (10)	0.0408 (11)	0.000	−0.0029 (8)	0.000
C3	0.0295 (10)	0.0338 (9)	0.0385 (11)	0.000	0.0023 (8)	0.000
C4	0.0343 (11)	0.0404 (10)	0.0334 (10)	0.000	−0.0020 (9)	0.000
C5	0.0275 (9)	0.0379 (10)	0.0389 (11)	0.000	−0.0002 (8)	0.000
C6	0.0276 (9)	0.0398 (10)	0.0347 (11)	0.000	0.0011 (8)	0.000
C7	0.0299 (11)	0.0568 (12)	0.0416 (12)	0.000	−0.0013 (9)	0.000
C8	0.0550 (16)	0.151 (3)	0.0315 (13)	0.000	−0.0049 (12)	0.000
C9	0.034	0.043	0.039	0.000	0.003	0.000
C10	0.063	0.098	0.041	0.000	0.018	0.000
C11	0.0341 (11)	0.0558 (12)	0.0319 (10)	0.000	0.0003 (9)	0.000
C12	0.0340 (12)	0.0849 (17)	0.0409 (13)	0.000	−0.0041 (10)	0.000

Geometric parameters (Å, º) top

O1—C9	1.1998 (14)	C4—C5	1.392 (3)
O2—C9	1.3272 (15)	C4—H4	0.9400
O2—C10	1.4544 (14)	C5—C6	1.395 (3)
O3—C7	1.195 (3)	C5—C11	1.445 (3)
O4—C7	1.319 (3)	C6—H6	0.9400
O4—C8	1.452 (3)	C8—H8A	0.9700
C1—C2	1.389 (3)	C8—H8B	0.9700
C1—C6	1.389 (3)	C8—H8C	0.9700
C1—C7	1.487 (3)	C10—H10A	0.9700
C2—C3	1.387 (3)	C10—H10B	0.9700
C2—H2	0.9400	C10—H10C	0.9700
C3—C4	1.391 (3)	C11—C12	1.166 (3)
C3—C9	1.4925 (18)	C12—H12	0.9400

C9—O2—C10	115.75 (10)	O3—C7—O4	123.6 (2)
C7—O4—C8	116.19 (18)	O3—C7—C1	124.21 (19)
C2—C1—C6	119.96 (18)	O4—C7—C1	112.23 (17)
C2—C1—C7	118.13 (17)	O4—C8—H8A	109.5
C6—C1—C7	121.91 (17)	O4—C8—H8B	109.5
C3—C2—C1	120.42 (17)	H8A—C8—H8B	109.5
C3—C2—H2	119.8	O4—C8—H8C	109.5
C1—C2—H2	119.8	H8A—C8—H8C	109.5
C2—C3—C4	119.39 (18)	H8B—C8—H8C	109.5
C2—C3—C9	118.53 (15)	O1—C9—O2	123.76 (10)
C4—C3—C9	122.09 (16)	O1—C9—C3	124.12 (11)
C3—C4—C5	120.83 (18)	O2—C9—C3	112.12 (9)
C3—C4—H4	119.6	O2—C10—H10A	109.5
C5—C4—H4	119.6	O2—C10—H10B	109.5
C4—C5—C6	119.18 (17)	H10A—C10—H10B	109.5
C4—C5—C11	119.98 (18)	O2—C10—H10C	109.5
C6—C5—C11	120.84 (17)	H10A—C10—H10C	109.5
C1—C6—C5	120.21 (17)	H10B—C10—H10C	109.5
C1—C6—H6	119.9	C12—C11—C5	179.5 (2)
C5—C6—H6	119.9	C11—C12—H12	180.0

C6—C1—C2—C3	0.000 (1)	C8—O4—C7—O3	0.000 (1)
C7—C1—C2—C3	180.000 (1)	C8—O4—C7—C1	180.000 (1)
C1—C2—C3—C4	0.000 (1)	C2—C1—C7—O3	0.000 (1)
C1—C2—C3—C9	180.000 (1)	C6—C1—C7—O3	180.000 (1)
C2—C3—C4—C5	0.000 (1)	C2—C1—C7—O4	180.000 (1)
C9—C3—C4—C5	180.000 (1)	C6—C1—C7—O4	0.000 (1)
C3—C4—C5—C6	0.000 (1)	C10—O2—C9—O1	0.000 (1)
C3—C4—C5—C11	180.000 (1)	C10—O2—C9—C3	180.000 (1)
C2—C1—C6—C5	0.000 (1)	C2—C3—C9—O1	0.000 (1)
C7—C1—C6—C5	180.000 (1)	C4—C3—C9—O1	180.000 (1)
C4—C5—C6—C1	0.000 (1)	C2—C3—C9—O2	180.000 (1)
C11—C5—C6—C1	180.000 (1)	C4—C3—C9—O2	0.000 (1)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O1ⁱ	0.94	2.29	3.223 (1)	172

Symmetry code: (i) x−1, y, z.

Funding information

We acknowledge the financial support by the Deutsche Forschungsgemeinschaft (DFG Priority Program 1362 `Porous Metal-Organic Frameworks').

References

Bruker (2014). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Desiraju, G. R., Ho, P. S., Kloo, L., Legon, A. C., Marquardt, R., Metrangolo, P., Politzer, P., Resnati, G. & Rissanen, K. (2013). Pure Appl. Chem. 85, 1711–1713. Web of Science CrossRef CAS Google Scholar
Desiraju, G. R. & Steiner, T. (1999). In The Weak Hydrogen Bond. Oxford University Press. Google Scholar
Desiraju, G. R., Vittal, J. J. & Ramanan, A. (2011). Crystal Engineering. Singapore: World Scientific Publications. Google Scholar
Doucet, H. & Hierso, J. C. (2007). Angew. Chem. Int. Ed. 46, 834–871. Web of Science CrossRef Google Scholar
Eddaoudi, M., Sava, D. F., Eubank, J. F., Adil, K. & Guillerm, V. (2015). Chem. Soc. Rev. 44, 228–249. Web of Science CrossRef CAS PubMed Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Furukawa, H., Cordova, K. E., O'Keeffe, M. & Yaghi, O. M. (2013). Science, 341, 1230444. Web of Science CrossRef PubMed Google Scholar
Gallagher, C. F. & Mocilac, P. (2012). CSD Communication (Refcode GOHRUS). CCDC, Cambridge, England. Google Scholar
Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179. Web of Science CSD CrossRef IUCr Journals Google Scholar
Hauptvogel, I. M., Seichter, W. & Weber, E. (2011). Supramol. Chem. 23, 398–406. Web of Science CrossRef Google Scholar
Hausdorf, S., Seichter, W., Weber, E. & Mertens, F. O. R. L. (2009). Dalton Trans. pp. 1107–1113. Web of Science CSD CrossRef Google Scholar
Havens, S. J. & Hergenrother, P. M. (1985). J. Org. Chem. 50, 1863–1865. CrossRef Web of Science Google Scholar
Lin, X., Jia, J., Zhao, X., Thomas, K. M., Blake, A. J., Walker, G. S., Champness, N. R., Hubberstey, P. & Schröder, M. (2006). Angew. Chem. Int. Ed. 45, 7358–7364. Web of Science CSD CrossRef CAS Google Scholar
MacGillivray, L. R. (2010). Metal-Organic Frameworks. Hoboken: Wiley. Google Scholar
Mazik, M. & König, A. (2006). J. Org. Chem. 71, 7854–7857. Web of Science CrossRef PubMed CAS Google Scholar
Parsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249–259. Web of Science CrossRef CAS IUCr Journals Google Scholar
Politzer, P., Lane, P., Concha, M. C., Ma, Y. & Murray, J. S. (2007). J. Mol. Model. 13, 305–311. Web of Science CrossRef PubMed CAS Google Scholar
Rafael, C. & Carmen, N. (2007). Chem. Rev. B107, 874–922. Google Scholar
Sheldrick, G. M. (2008a). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008b). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Tiekink, E. R. T. & Zukerman-Schpector, J. (2012). In The Importance of Pi-Interactions in Crystal Engineering. Frontiers in Crystal Engineering. Chichester: Wiley. Google Scholar
Zheng, B., Liang, Z., Li, G., Huo, Q. & Liu, Y. (2010). Cryst. Growth Des. 10, 3405–3409. Web of Science CrossRef Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 74| Part 8| August 2018| Pages 1093-1096

https://doi.org/10.1107/S205698901800912X

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text
		Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text
		Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

research communications\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structures of di­methyl 5-iodo­iso­phthal­ate and di­methyl 5-ethynyl­iso­phthal­ate

1. Chemical context

2. Structural commentary

3. Supra­molecular features

4. Database survey

5. Synthesis and crystallization

6. Refinement

Supporting information

Funding information

References

research communications

Crystal structures of dimethyl 5-iodoisophthalate and dimethyl 5-ethynylisophthalate

3. Supramolecular features