Bis(2-formyl­phen­yl) benzene-1,2-di­carboxyl­ate

Mohamed, S.K.; Mague, J.T.; Akkurt, M.; Hawaiz, F.E.; Ayoob, M.M.; Hussein, A.J.

doi:10.1107/S2414314618002511

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 3| Part 2| February 2018| x180251

https://doi.org/10.1107/S2414314618002511

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Bis(2-formylphenyl) benzene-1,2-dicarboxylate

Shaaban K. Mohamed,^a,^b Joel T. Mague,^c Mehmet Akkurt,^d Farouq E. Hawaiz,^e ^* Mzgin M. Ayoob ^e and Awaz J. Hussein ^e

^aChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, ^bChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, ^cDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, ^dDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, and ^eChemistry Department, College of Education, Salahaddin University-Hawler, Erbil, Kurdistan Region, Iraq
^*Correspondence e-mail: shaabankamel@yahoo.com

Edited by H. Ishida, Okayama University, Japan (Received 19 January 2018; accepted 12 February 2018; online 23 February 2018)

The asymmetric unit of the title compound, C₂₂H₁₄O₆, consists of two independent molecules differing in the orientations of the ester groups. In one molecule, the two terminal benzene rings are inclined to the central benzene ring by 4.99 (13) and 77.46 (13)°, while in the other the corresponding angles are 11.03 (13) and 88.09 (12)°. In the crystal, molecules are connected into a ribbon structure running along [101] via C—H⋯O and C—H⋯π interactions. Adjacent ribbons are further linked by additional C—H⋯O and C—H⋯π interactions. The crystal studied was a non-merohedral twin [twin law (0.986 − 0.073 − 0.008, 0.323 1.036 0.148, −0.121 − 0.102 0.942)], the ratio of components being 0.937 (4):0.063 (4).

Keywords: crystal structure; hydrogen bond; π–π stacking; bis-aldehydes.

CCDC reference: 1823527

Structure description

The synthesis of bis-aldehydes is of great importance as this bi-functional unit is a useful synthon for the preparation of different intermediates such as bis-chalcones and bis-imines, which can be easily converted to many important pharmaceutical and biologically active heterocyclic compounds such as pyrazolines (Hawaiz & Shekh Omer, 2017 ) and thiazolidinones (Hussein & Azeez, 2013 ). Based on such findings, we herein report the synthesis and crystal structure of the title compound.

The asymmetric unit of the title compound consists of two independent molecules, which differ in the orientations of the ester groups (Fig. 1). In one molecule, the terminal C8–C13 and C16–C21 benzene rings are inclined to the central C1–C6 ring by 4.99 (13) and 77.46 (13)°, respectively, while in the other the C30–C35 and C38–C43 benzene rings are inclined to the C23–C28 ring by 88.09 (12) and 11.03 (13)°, respectively.

Figure 1
The asymmetric unit of the title compound with labeling scheme and 50% probability ellipsoids. The C—H⋯π interaction is shown as a dashed line.

In the crystal (Fig. 2), the molecules are linked into a ribbon structure running along [101] via three predominant C—H⋯O hydrogen bonds and a C—H⋯π interaction (C3—H3⋯O10ⁱ, C22—H22⋯O3ⁱ, C36—H36⋯O12ⁱⁱⁱ and C11—H11⋯Cg5; symmetry codes as in Table 1; Cg5 is the centroid of the C30–C35 benzene ring). The ribbons are further linked by other weak C—H⋯O and C—H⋯π interactions (C18—H18⋯O6ⁱⁱ, C32—H32⋯O9ⁱⁱ and C26—H26⋯Cg3^iv; Table 1; Cg3 is the centroid of the C16–C21 benzene ring).

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 and Cg5 are the centroids of the C16–C21 and C30–C35 benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O10ⁱ	0.95	2.35	3.221 (3)	152
C18—H18⋯O6ⁱⁱ	0.95	2.55	3.430 (3)	155
C22—H22⋯O3ⁱ	0.95	2.29	3.147 (3)	149
C32—H32⋯O9ⁱⁱ	0.95	2.54	3.422 (3)	155
C36—H36⋯O12ⁱⁱⁱ	0.95	2.41	3.205 (3)	141
C11—H11⋯Cg5	0.95	2.75	3.664 (3)	162
C26—H26⋯Cg3^iv	0.95	2.68	3.546 (3)	152
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x+1, y, z; (iii) -x, -y+1, -z; (iv) -x+1, -y+1, -z.

Figure 2
A packing diagram viewed along the a axis, showing the C—H⋯O hydrogen bonds (dashed lines).

Synthesis and crystallization

A mixture of phthaloyl chloride (0.5 g, 0.0025 mol), 2-hydroxybenzaldehyde (0.61 g, 0.005 mol) and triethylamine (0.5 g, 0.005 mol) in dioxane (20 ml) was stirred for a few minutes. The solid amine salt (Et₃N·HCl) was separated by filtration and the filtrate was refluxed for 30 min. On cooling, good quality crystals of the title compound were obtained, filtered and dried (0.9 g, 92%).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The crystal studied was a non-merohedral twin [twin law (0.986 − 0.073 − 0.008, 0.323 1.036 0.148, −0.121 − 0.102 0.942)], the refined ratio of the two domains being 0.937 (4) and 0.063 (4).

Table 2
Experimental details

Crystal data
Chemical formula	C₂₂H₁₄O₆
M_r	374.33
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	150
a, b, c (Å)	8.1833 (2), 15.4412 (4), 15.5250 (4)
α, β, γ (°)	110.657 (1), 104.919 (1), 90.516 (1)
V (Å³)	1762.89 (8)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	0.87
Crystal size (mm)	0.17 × 0.12 × 0.08

Data collection
Diffractometer	Bruker D8 VENTURE PHOTON 100 CMOS
Absorption correction	Multi-scan (TWINABS; Sheldrick, 2009 )
T_min, T_max	0.87, 0.94
No. of measured, independent and observed [I > 2σ(I)] reflections	26732, 26732, 16950
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.619

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.153, 1.03
No. of reflections	26732
No. of parameters	507
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.49, −0.37
Computer programs: APEX3 and SAINT (Bruker, 2016 ), SHELXT2014 (Sheldrick, 2015a ), SHELXL2018 (Sheldrick, 2015b ), ORTEP-3 for Windows and WinGX (Farrugia, 2012 ) and PLATON (Spek, 2015 ).

Structural data

CCDC reference: 1823527

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2414314618002511/is4025sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314618002511/is4025Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314618002511/is4025Isup3.cml

checkCIF report

Computing details top

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXS2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2015).

Bis(2-formylphenyl) benzene-1,2-dicarboxylate top

Crystal data top

C₂₂H₁₄O₆	Z = 4
M_r = 374.33	F(000) = 776
Triclinic, P1	D_x = 1.410 Mg m⁻³
a = 8.1833 (2) Å	Cu Kα radiation, λ = 1.54178 Å
b = 15.4412 (4) Å	Cell parameters from 9890 reflections
c = 15.5250 (4) Å	θ = 3.1–72.5°
α = 110.657 (1)°	µ = 0.87 mm⁻¹
β = 104.919 (1)°	T = 150 K
γ = 90.516 (1)°	Block, colourless
V = 1762.89 (8) Å³	0.17 × 0.12 × 0.08 mm

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	26732 independent reflections
Radiation source: INCOATEC IµS micro-focus source	16950 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.032
Detector resolution: 10.4167 pixels mm^-1	θ_max = 72.6°, θ_min = 3.2°
ω scans	h = −10→9
Absorption correction: multi-scan (TWINABS; Sheldrick, 2009)	k = −18→19
T_min = 0.87, T_max = 0.94	l = −19→19
26732 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.054	w = 1/[σ²(F_o²) + (0.0601P)² + 0.2628P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.153	(Δ/σ)_max < 0.001
S = 1.03	Δρ_max = 0.49 e Å⁻³
26732 reflections	Δρ_min = −0.36 e Å⁻³
507 parameters	Extinction correction: SHELXL2018 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0039 (5)

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. Analysis of 1273 reflections having I/σ(I) > 14 chosen from the full data set with CELL_NOW indicated the crystal to belong to the triclinic system and to contain two components rotated by 10.9° about the real axis [1 -1/4 -3/4]. The refined twin law was (0.986 -0.073 -0.008 0.323 1.036 0.148 -0.121 -0.102 0.942). There were 27338 single reflections, 13636 from component 1 and 13622 from component 2 and 126 full or partial overlaps. The refined twin fractions are 0.937 (4) and 0.063 (4).

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

	x	y	z	U_iso*/U_eq
O1	0.5734 (2)	0.42829 (12)	0.41266 (11)	0.0428 (4)
O2	0.80387 (19)	0.52408 (10)	0.51789 (10)	0.0311 (3)
O3	0.6591 (3)	0.77157 (12)	0.65877 (14)	0.0543 (5)
O4	0.8409 (3)	0.30317 (11)	0.36575 (11)	0.0461 (5)
O5	0.7698 (2)	0.16274 (10)	0.36799 (10)	0.0356 (4)
O6	0.3825 (2)	0.04440 (15)	0.12472 (13)	0.0543 (5)
C1	0.7376 (3)	0.38678 (15)	0.54099 (14)	0.0300 (5)
C2	0.7252 (3)	0.42400 (16)	0.63447 (15)	0.0355 (5)
H2	0.699632	0.486288	0.659733	0.043*
C3	0.7502 (3)	0.37001 (18)	0.69075 (15)	0.0405 (6)
H3	0.741109	0.395358	0.754464	0.049*
C4	0.7882 (3)	0.27987 (17)	0.65466 (16)	0.0419 (6)
H4	0.807154	0.243657	0.693953	0.050*
C5	0.7989 (3)	0.24170 (16)	0.56124 (16)	0.0370 (5)
H5	0.823710	0.179185	0.536468	0.044*
C6	0.7734 (3)	0.29486 (15)	0.50353 (14)	0.0304 (5)
C7	0.6941 (3)	0.44492 (14)	0.48077 (14)	0.0301 (5)
C8	0.7694 (3)	0.58694 (15)	0.46973 (15)	0.0308 (5)
C9	0.7879 (3)	0.56301 (17)	0.37874 (17)	0.0398 (5)
H9	0.823531	0.504487	0.347907	0.048*
C10	0.7532 (4)	0.62625 (19)	0.33305 (18)	0.0473 (6)
H10	0.764553	0.610711	0.270116	0.057*
C11	0.7024 (4)	0.71172 (19)	0.3783 (2)	0.0485 (6)
H11	0.677560	0.754195	0.346147	0.058*
C12	0.6877 (3)	0.73525 (17)	0.47004 (19)	0.0415 (6)
H12	0.654548	0.794425	0.501197	0.050*
C13	0.7211 (3)	0.67281 (15)	0.51767 (16)	0.0322 (5)
C14	0.7065 (3)	0.69903 (16)	0.61646 (17)	0.0366 (5)
H14	0.736100	0.656566	0.648284	0.044*
C15	0.7984 (3)	0.25722 (15)	0.40591 (15)	0.0321 (5)
C16	0.8110 (3)	0.11665 (14)	0.28143 (15)	0.0312 (5)
C17	0.9792 (3)	0.10939 (17)	0.28322 (18)	0.0389 (5)
H17	1.066574	0.136746	0.341619	0.047*
C18	1.0193 (3)	0.06153 (18)	0.19846 (19)	0.0430 (6)
H18	1.135038	0.057669	0.198343	0.052*
C19	0.8911 (3)	0.01932 (17)	0.11396 (17)	0.0411 (6)
H19	0.919116	−0.013859	0.056228	0.049*
C20	0.7233 (3)	0.02544 (16)	0.11364 (16)	0.0361 (5)
H20	0.635927	−0.004304	0.055714	0.043*
C21	0.6803 (3)	0.07516 (15)	0.19799 (15)	0.0314 (5)
C22	0.4995 (3)	0.07987 (17)	0.19666 (17)	0.0392 (5)
H22	0.473487	0.112361	0.255175	0.047*
O7	0.4612 (2)	0.68794 (11)	0.13827 (11)	0.0421 (4)
O8	0.4103 (2)	0.83121 (10)	0.13783 (10)	0.0343 (4)
O9	0.2576 (2)	0.96930 (16)	0.37361 (13)	0.0564 (5)
O10	0.1470 (2)	0.56231 (10)	0.07902 (10)	0.0344 (4)
O11	0.2885 (2)	0.47254 (10)	−0.02015 (10)	0.0307 (3)
O12	−0.0216 (2)	0.22964 (12)	−0.14418 (12)	0.0445 (4)
C23	0.1995 (3)	0.60988 (15)	−0.04291 (14)	0.0287 (4)
C24	0.1012 (3)	0.57557 (16)	−0.13781 (14)	0.0330 (5)
H24	0.050852	0.512756	−0.166770	0.040*
C25	0.0767 (3)	0.63330 (17)	−0.19027 (15)	0.0373 (5)
H25	0.010341	0.609567	−0.255340	0.045*
C26	0.1480 (3)	0.72480 (17)	−0.14857 (16)	0.0391 (5)
H26	0.130032	0.763998	−0.184761	0.047*
C27	0.2459 (3)	0.75960 (16)	−0.05380 (16)	0.0361 (5)
H27	0.294766	0.822699	−0.025161	0.043*
C28	0.2730 (3)	0.70253 (15)	−0.00049 (14)	0.0301 (5)
C29	0.3900 (3)	0.73626 (15)	0.09826 (15)	0.0306 (5)
C30	0.5356 (3)	0.87237 (14)	0.22533 (15)	0.0298 (5)
C31	0.7047 (3)	0.86742 (16)	0.22777 (17)	0.0373 (5)
H31	0.736192	0.834619	0.171062	0.045*
C32	0.8280 (3)	0.91077 (17)	0.3137 (2)	0.0421 (6)
H32	0.944924	0.907067	0.316452	0.051*
C33	0.7813 (3)	0.95957 (17)	0.39587 (18)	0.0420 (6)
H33	0.866240	0.988609	0.455021	0.050*
C34	0.6121 (3)	0.96609 (17)	0.39196 (16)	0.0377 (5)
H34	0.581216	1.000895	0.448302	0.045*
C35	0.4856 (3)	0.92221 (15)	0.30632 (15)	0.0303 (5)
C36	0.3052 (3)	0.93132 (17)	0.30308 (16)	0.0374 (5)
H36	0.222211	0.906132	0.242657	0.045*
C37	0.2092 (3)	0.54900 (14)	0.01415 (14)	0.0274 (4)
C38	0.3023 (3)	0.41139 (15)	0.03022 (15)	0.0303 (5)
C39	0.4192 (3)	0.43683 (17)	0.11928 (16)	0.0377 (5)
H39	0.488630	0.494788	0.146572	0.045*
C40	0.4332 (3)	0.37622 (19)	0.16793 (17)	0.0444 (6)
H40	0.512796	0.392745	0.229272	0.053*
C41	0.3319 (4)	0.29152 (18)	0.12787 (19)	0.0462 (6)
H41	0.341554	0.250581	0.162010	0.055*
C42	0.2169 (3)	0.26673 (17)	0.03832 (18)	0.0402 (5)
H42	0.148523	0.208449	0.010831	0.048*
C43	0.2006 (3)	0.32701 (15)	−0.01224 (15)	0.0317 (5)
C44	0.0783 (3)	0.29935 (15)	−0.10841 (16)	0.0335 (5)
H44	0.078098	0.338378	−0.143977	0.040*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0479 (10)	0.0383 (9)	0.0337 (8)	−0.0107 (8)	−0.0082 (7)	0.0175 (7)
O2	0.0334 (8)	0.0251 (8)	0.0309 (7)	−0.0009 (6)	0.0035 (6)	0.0097 (6)
O3	0.0635 (12)	0.0340 (10)	0.0613 (11)	0.0048 (9)	0.0306 (10)	0.0033 (8)
O4	0.0803 (13)	0.0286 (8)	0.0332 (8)	−0.0009 (8)	0.0221 (8)	0.0116 (7)
O5	0.0536 (10)	0.0238 (8)	0.0294 (8)	−0.0004 (7)	0.0162 (7)	0.0066 (6)
O6	0.0378 (10)	0.0713 (13)	0.0448 (10)	0.0075 (9)	0.0083 (8)	0.0129 (9)
C1	0.0334 (11)	0.0281 (11)	0.0238 (9)	−0.0020 (9)	0.0017 (8)	0.0087 (8)
C2	0.0424 (13)	0.0322 (12)	0.0245 (10)	0.0006 (10)	0.0041 (9)	0.0053 (9)
C3	0.0504 (14)	0.0449 (14)	0.0210 (10)	−0.0025 (11)	0.0054 (9)	0.0093 (9)
C4	0.0564 (15)	0.0416 (14)	0.0291 (11)	−0.0011 (12)	0.0051 (10)	0.0195 (10)
C5	0.0499 (14)	0.0293 (11)	0.0302 (11)	0.0006 (10)	0.0063 (10)	0.0124 (9)
C6	0.0370 (12)	0.0267 (11)	0.0235 (10)	−0.0026 (9)	0.0030 (8)	0.0084 (8)
C7	0.0356 (12)	0.0248 (11)	0.0252 (10)	−0.0010 (9)	0.0053 (9)	0.0060 (8)
C8	0.0302 (11)	0.0267 (11)	0.0333 (11)	−0.0022 (9)	0.0041 (9)	0.0119 (9)
C9	0.0460 (14)	0.0350 (13)	0.0379 (12)	−0.0016 (11)	0.0142 (10)	0.0110 (10)
C10	0.0552 (16)	0.0504 (16)	0.0379 (13)	−0.0102 (13)	0.0115 (11)	0.0194 (11)
C11	0.0520 (16)	0.0434 (15)	0.0540 (15)	−0.0054 (12)	0.0044 (12)	0.0300 (13)
C12	0.0390 (13)	0.0312 (12)	0.0524 (14)	0.0003 (10)	0.0060 (11)	0.0180 (11)
C13	0.0295 (11)	0.0271 (11)	0.0356 (11)	−0.0016 (9)	0.0052 (9)	0.0092 (9)
C14	0.0351 (12)	0.0287 (12)	0.0400 (12)	−0.0026 (10)	0.0091 (10)	0.0064 (9)
C15	0.0432 (13)	0.0240 (10)	0.0269 (10)	0.0006 (9)	0.0066 (9)	0.0089 (8)
C16	0.0429 (13)	0.0228 (10)	0.0303 (10)	0.0032 (9)	0.0137 (9)	0.0102 (8)
C17	0.0391 (13)	0.0350 (13)	0.0426 (13)	−0.0006 (10)	0.0084 (10)	0.0164 (10)
C18	0.0365 (13)	0.0416 (14)	0.0591 (15)	0.0083 (11)	0.0221 (12)	0.0218 (12)
C19	0.0515 (15)	0.0351 (13)	0.0428 (13)	0.0088 (11)	0.0264 (11)	0.0120 (10)
C20	0.0430 (13)	0.0326 (12)	0.0309 (11)	0.0038 (10)	0.0124 (9)	0.0080 (9)
C21	0.0381 (12)	0.0260 (11)	0.0327 (11)	0.0061 (9)	0.0136 (9)	0.0112 (9)
C22	0.0431 (14)	0.0375 (13)	0.0387 (12)	0.0112 (11)	0.0169 (11)	0.0119 (10)
O7	0.0549 (11)	0.0288 (8)	0.0346 (8)	0.0018 (8)	−0.0017 (7)	0.0123 (7)
O8	0.0441 (9)	0.0246 (8)	0.0281 (7)	0.0035 (7)	0.0041 (6)	0.0066 (6)
O9	0.0343 (9)	0.0830 (15)	0.0398 (9)	0.0076 (9)	0.0121 (7)	0.0070 (9)
O10	0.0497 (9)	0.0327 (8)	0.0259 (7)	0.0115 (7)	0.0168 (7)	0.0122 (6)
O11	0.0392 (8)	0.0275 (8)	0.0298 (7)	0.0077 (7)	0.0149 (6)	0.0118 (6)
O12	0.0445 (10)	0.0334 (9)	0.0472 (10)	0.0009 (8)	0.0099 (8)	0.0069 (7)
C23	0.0352 (11)	0.0284 (11)	0.0241 (9)	0.0058 (9)	0.0112 (8)	0.0092 (8)
C24	0.0403 (12)	0.0314 (11)	0.0244 (10)	0.0031 (10)	0.0089 (9)	0.0070 (9)
C25	0.0455 (13)	0.0430 (13)	0.0232 (10)	0.0084 (11)	0.0085 (9)	0.0126 (9)
C26	0.0532 (15)	0.0401 (13)	0.0305 (11)	0.0096 (11)	0.0135 (10)	0.0195 (10)
C27	0.0486 (14)	0.0306 (12)	0.0316 (11)	0.0044 (10)	0.0133 (10)	0.0129 (9)
C28	0.0371 (12)	0.0290 (11)	0.0254 (10)	0.0051 (9)	0.0108 (9)	0.0099 (8)
C29	0.0397 (12)	0.0252 (10)	0.0271 (10)	0.0029 (9)	0.0106 (9)	0.0089 (8)
C30	0.0340 (11)	0.0232 (10)	0.0301 (10)	0.0004 (9)	0.0053 (9)	0.0098 (8)
C31	0.0397 (13)	0.0308 (12)	0.0468 (13)	0.0070 (10)	0.0191 (10)	0.0158 (10)
C32	0.0286 (12)	0.0361 (13)	0.0645 (16)	0.0029 (10)	0.0134 (11)	0.0217 (12)
C33	0.0299 (12)	0.0375 (13)	0.0464 (13)	−0.0044 (10)	−0.0022 (10)	0.0104 (11)
C34	0.0337 (12)	0.0385 (13)	0.0333 (11)	−0.0008 (10)	0.0046 (9)	0.0075 (10)
C35	0.0281 (11)	0.0291 (11)	0.0312 (10)	−0.0011 (9)	0.0061 (8)	0.0099 (9)
C36	0.0297 (12)	0.0404 (13)	0.0341 (11)	0.0000 (10)	0.0034 (9)	0.0081 (10)
C37	0.0318 (11)	0.0249 (10)	0.0219 (9)	0.0016 (9)	0.0054 (8)	0.0057 (8)
C38	0.0350 (11)	0.0297 (11)	0.0314 (10)	0.0109 (10)	0.0143 (9)	0.0136 (9)
C39	0.0389 (13)	0.0386 (13)	0.0343 (11)	0.0081 (11)	0.0097 (9)	0.0121 (10)
C40	0.0494 (15)	0.0519 (15)	0.0328 (12)	0.0187 (13)	0.0093 (10)	0.0177 (11)
C41	0.0610 (17)	0.0452 (15)	0.0471 (14)	0.0219 (13)	0.0214 (12)	0.0296 (12)
C42	0.0494 (14)	0.0324 (12)	0.0453 (13)	0.0103 (11)	0.0196 (11)	0.0172 (10)
C43	0.0359 (12)	0.0287 (11)	0.0332 (11)	0.0098 (10)	0.0147 (9)	0.0108 (9)
C44	0.0367 (12)	0.0284 (11)	0.0353 (11)	0.0084 (10)	0.0142 (9)	0.0085 (9)

Geometric parameters (Å, º) top

O1—C7	1.194 (3)	O7—C29	1.196 (3)
O2—C7	1.360 (3)	O8—C29	1.365 (3)
O2—C8	1.410 (3)	O8—C30	1.401 (3)
O3—C14	1.207 (3)	O9—C36	1.211 (3)
O4—C15	1.197 (3)	O10—C37	1.198 (2)
O5—C15	1.359 (3)	O11—C37	1.359 (3)
O5—C16	1.410 (2)	O11—C38	1.412 (2)
O6—C22	1.213 (3)	O12—C44	1.210 (3)
C1—C2	1.391 (3)	C23—C24	1.389 (3)
C1—C6	1.397 (3)	C23—C28	1.399 (3)
C1—C7	1.494 (3)	C23—C37	1.493 (3)
C2—C3	1.388 (3)	C24—C25	1.389 (3)
C2—H2	0.9500	C24—H24	0.9500
C3—C4	1.377 (4)	C25—C26	1.379 (3)
C3—H3	0.9500	C25—H25	0.9500
C4—C5	1.386 (3)	C26—C27	1.387 (3)
C4—H4	0.9500	C26—H26	0.9500
C5—C6	1.395 (3)	C27—C28	1.391 (3)
C5—H5	0.9500	C27—H27	0.9500
C6—C15	1.489 (3)	C28—C29	1.487 (3)
C8—C9	1.377 (3)	C30—C31	1.378 (3)
C8—C13	1.390 (3)	C30—C35	1.389 (3)
C9—C10	1.388 (4)	C31—C32	1.382 (4)
C9—H9	0.9500	C31—H31	0.9500
C10—C11	1.384 (4)	C32—C33	1.385 (4)
C10—H10	0.9500	C32—H32	0.9500
C11—C12	1.377 (4)	C33—C34	1.377 (3)
C11—H11	0.9500	C33—H33	0.9500
C12—C13	1.398 (3)	C34—C35	1.393 (3)
C12—H12	0.9500	C34—H34	0.9500
C13—C14	1.479 (3)	C35—C36	1.474 (3)
C14—H14	0.9500	C36—H36	0.9500
C16—C17	1.376 (3)	C38—C39	1.382 (3)
C16—C21	1.386 (3)	C38—C43	1.384 (3)
C17—C18	1.388 (4)	C39—C40	1.384 (3)
C17—H17	0.9500	C39—H39	0.9500
C18—C19	1.386 (4)	C40—C41	1.388 (4)
C18—H18	0.9500	C40—H40	0.9500
C19—C20	1.376 (4)	C41—C42	1.382 (4)
C19—H19	0.9500	C41—H41	0.9500
C20—C21	1.400 (3)	C42—C43	1.401 (3)
C20—H20	0.9500	C42—H42	0.9500
C21—C22	1.477 (3)	C43—C44	1.479 (3)
C22—H22	0.9500	C44—H44	0.9500

C7—O2—C8	115.88 (16)	C29—O8—C30	116.81 (16)
C15—O5—C16	117.47 (16)	C37—O11—C38	115.03 (15)
C2—C1—C6	120.02 (19)	C24—C23—C28	119.85 (19)
C2—C1—C7	117.62 (19)	C24—C23—C37	118.41 (19)
C6—C1—C7	122.07 (18)	C28—C23—C37	121.44 (18)
C3—C2—C1	119.9 (2)	C25—C24—C23	119.9 (2)
C3—C2—H2	120.0	C25—C24—H24	120.1
C1—C2—H2	120.0	C23—C24—H24	120.1
C4—C3—C2	120.3 (2)	C26—C25—C24	120.5 (2)
C4—C3—H3	119.9	C26—C25—H25	119.8
C2—C3—H3	119.9	C24—C25—H25	119.8
C3—C4—C5	120.3 (2)	C25—C26—C27	120.0 (2)
C3—C4—H4	119.8	C25—C26—H26	120.0
C5—C4—H4	119.8	C27—C26—H26	120.0
C4—C5—C6	120.2 (2)	C26—C27—C28	120.3 (2)
C4—C5—H5	119.9	C26—C27—H27	119.9
C6—C5—H5	119.9	C28—C27—H27	119.9
C5—C6—C1	119.31 (19)	C27—C28—C23	119.5 (2)
C5—C6—C15	120.6 (2)	C27—C28—C29	120.9 (2)
C1—C6—C15	119.91 (18)	C23—C28—C29	119.39 (18)
O1—C7—O2	123.6 (2)	O7—C29—O8	123.5 (2)
O1—C7—C1	125.3 (2)	O7—C29—C28	125.5 (2)
O2—C7—C1	110.90 (18)	O8—C29—C28	111.05 (18)
C9—C8—C13	122.2 (2)	C31—C30—C35	121.8 (2)
C9—C8—O2	119.8 (2)	C31—C30—O8	119.43 (19)
C13—C8—O2	118.03 (19)	C35—C30—O8	118.69 (19)
C8—C9—C10	118.6 (2)	C30—C31—C32	119.2 (2)
C8—C9—H9	120.7	C30—C31—H31	120.4
C10—C9—H9	120.7	C32—C31—H31	120.4
C11—C10—C9	120.6 (2)	C31—C32—C33	120.1 (2)
C11—C10—H10	119.7	C31—C32—H32	119.9
C9—C10—H10	119.7	C33—C32—H32	119.9
C12—C11—C10	120.1 (2)	C34—C33—C32	120.1 (2)
C12—C11—H11	120.0	C34—C33—H33	119.9
C10—C11—H11	120.0	C32—C33—H33	119.9
C11—C12—C13	120.6 (2)	C33—C34—C35	120.8 (2)
C11—C12—H12	119.7	C33—C34—H34	119.6
C13—C12—H12	119.7	C35—C34—H34	119.6
C8—C13—C12	118.0 (2)	C30—C35—C34	118.0 (2)
C8—C13—C14	121.8 (2)	C30—C35—C36	121.96 (19)
C12—C13—C14	120.2 (2)	C34—C35—C36	120.01 (19)
O3—C14—C13	123.4 (2)	O9—C36—C35	123.3 (2)
O3—C14—H14	118.3	O9—C36—H36	118.4
C13—C14—H14	118.3	C35—C36—H36	118.4
O4—C15—O5	123.68 (19)	O10—C37—O11	123.38 (19)
O4—C15—C6	125.1 (2)	O10—C37—C23	124.77 (19)
O5—C15—C6	111.23 (17)	O11—C37—C23	111.73 (16)
C17—C16—C21	121.9 (2)	C39—C38—C43	122.2 (2)
C17—C16—O5	119.1 (2)	C39—C38—O11	119.0 (2)
C21—C16—O5	118.9 (2)	C43—C38—O11	118.81 (19)
C16—C17—C18	119.0 (2)	C38—C39—C40	118.7 (2)
C16—C17—H17	120.5	C38—C39—H39	120.6
C18—C17—H17	120.5	C40—C39—H39	120.6
C19—C18—C17	120.2 (2)	C39—C40—C41	120.6 (2)
C19—C18—H18	119.9	C39—C40—H40	119.7
C17—C18—H18	119.9	C41—C40—H40	119.7
C20—C19—C18	120.1 (2)	C42—C41—C40	120.0 (2)
C20—C19—H19	120.0	C42—C41—H41	120.0
C18—C19—H19	120.0	C40—C41—H41	120.0
C19—C20—C21	120.5 (2)	C41—C42—C43	120.4 (2)
C19—C20—H20	119.7	C41—C42—H42	119.8
C21—C20—H20	119.7	C43—C42—H42	119.8
C16—C21—C20	118.2 (2)	C38—C43—C42	118.1 (2)
C16—C21—C22	121.97 (19)	C38—C43—C44	121.9 (2)
C20—C21—C22	119.8 (2)	C42—C43—C44	119.9 (2)
O6—C22—C21	123.4 (2)	O12—C44—C43	123.5 (2)
O6—C22—H22	118.3	O12—C44—H44	118.3
C21—C22—H22	118.3	C43—C44—H44	118.3

C6—C1—C2—C3	0.7 (3)	C28—C23—C24—C25	0.2 (3)
C7—C1—C2—C3	174.6 (2)	C37—C23—C24—C25	174.05 (19)
C1—C2—C3—C4	0.4 (4)	C23—C24—C25—C26	−0.6 (3)
C2—C3—C4—C5	−1.1 (4)	C24—C25—C26—C27	0.4 (4)
C3—C4—C5—C6	0.8 (4)	C25—C26—C27—C28	0.1 (4)
C4—C5—C6—C1	0.2 (4)	C26—C27—C28—C23	−0.5 (3)
C4—C5—C6—C15	175.0 (2)	C26—C27—C28—C29	174.5 (2)
C2—C1—C6—C5	−0.9 (3)	C24—C23—C28—C27	0.3 (3)
C7—C1—C6—C5	−174.6 (2)	C37—C23—C28—C27	−173.3 (2)
C2—C1—C6—C15	−175.8 (2)	C24—C23—C28—C29	−174.7 (2)
C7—C1—C6—C15	10.5 (3)	C37—C23—C28—C29	11.6 (3)
C8—O2—C7—O1	−1.1 (3)	C30—O8—C29—O7	7.1 (3)
C8—O2—C7—C1	−176.66 (17)	C30—O8—C29—C28	−171.30 (18)
C2—C1—C7—O1	−111.7 (3)	C27—C28—C29—O7	−156.0 (2)
C6—C1—C7—O1	62.1 (3)	C23—C28—C29—O7	19.0 (3)
C2—C1—C7—O2	63.7 (3)	C27—C28—C29—O8	22.4 (3)
C6—C1—C7—O2	−122.5 (2)	C23—C28—C29—O8	−162.62 (18)
C7—O2—C8—C9	−68.1 (3)	C29—O8—C30—C31	69.3 (3)
C7—O2—C8—C13	113.4 (2)	C29—O8—C30—C35	−114.7 (2)
C13—C8—C9—C10	−1.5 (4)	C35—C30—C31—C32	2.1 (3)
O2—C8—C9—C10	−179.9 (2)	O8—C30—C31—C32	177.9 (2)
C8—C9—C10—C11	0.4 (4)	C30—C31—C32—C33	−0.9 (4)
C9—C10—C11—C12	0.8 (4)	C31—C32—C33—C34	−0.8 (4)
C10—C11—C12—C13	−1.0 (4)	C32—C33—C34—C35	1.5 (4)
C9—C8—C13—C12	1.2 (3)	C31—C30—C35—C34	−1.4 (3)
O2—C8—C13—C12	179.7 (2)	O8—C30—C35—C34	−177.30 (19)
C9—C8—C13—C14	−178.1 (2)	C31—C30—C35—C36	177.1 (2)
O2—C8—C13—C14	0.4 (3)	O8—C30—C35—C36	1.2 (3)
C11—C12—C13—C8	0.1 (4)	C33—C34—C35—C30	−0.3 (3)
C11—C12—C13—C14	179.4 (2)	C33—C34—C35—C36	−178.9 (2)
C8—C13—C14—O3	−177.2 (2)	C30—C35—C36—O9	175.2 (2)
C12—C13—C14—O3	3.4 (4)	C34—C35—C36—O9	−6.3 (4)
C16—O5—C15—O4	7.3 (3)	C38—O11—C37—O10	−3.7 (3)
C16—O5—C15—C6	−171.59 (19)	C38—O11—C37—C23	−179.93 (17)
C5—C6—C15—O4	−151.2 (3)	C24—C23—C37—O10	−110.6 (2)
C1—C6—C15—O4	23.6 (4)	C28—C23—C37—O10	63.2 (3)
C5—C6—C15—O5	27.7 (3)	C24—C23—C37—O11	65.6 (3)
C1—C6—C15—O5	−157.6 (2)	C28—C23—C37—O11	−120.7 (2)
C15—O5—C16—C17	75.0 (3)	C37—O11—C38—C39	−74.2 (2)
C15—O5—C16—C21	−108.8 (2)	C37—O11—C38—C43	107.2 (2)
C21—C16—C17—C18	2.0 (3)	C43—C38—C39—C40	−0.9 (3)
O5—C16—C17—C18	178.0 (2)	O11—C38—C39—C40	−179.45 (19)
C16—C17—C18—C19	−2.0 (4)	C38—C39—C40—C41	0.1 (3)
C17—C18—C19—C20	0.6 (4)	C39—C40—C41—C42	0.6 (4)
C18—C19—C20—C21	0.8 (4)	C40—C41—C42—C43	−0.6 (4)
C17—C16—C21—C20	−0.6 (3)	C39—C38—C43—C42	0.8 (3)
O5—C16—C21—C20	−176.64 (18)	O11—C38—C43—C42	179.45 (18)
C17—C16—C21—C22	177.6 (2)	C39—C38—C43—C44	−178.7 (2)
O5—C16—C21—C22	1.6 (3)	O11—C38—C43—C44	−0.1 (3)
C19—C20—C21—C16	−0.8 (3)	C41—C42—C43—C38	−0.1 (3)
C19—C20—C21—C22	−179.1 (2)	C41—C42—C43—C44	179.4 (2)
C16—C21—C22—O6	179.9 (2)	C38—C43—C44—O12	−173.9 (2)
C20—C21—C22—O6	−1.9 (4)	C42—C43—C44—O12	6.5 (3)

Hydrogen-bond geometry (Å, º) top

Cg3 and Cg5 are the centroids of the C16–C21 and C30–C35 benzene rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O10ⁱ	0.95	2.35	3.221 (3)	152
C18—H18···O6ⁱⁱ	0.95	2.55	3.430 (3)	155
C22—H22···O3ⁱ	0.95	2.29	3.147 (3)	149
C32—H32···O9ⁱⁱ	0.95	2.54	3.422 (3)	155
C36—H36···O12ⁱⁱⁱ	0.95	2.41	3.205 (3)	141
C11—H11···Cg5	0.95	2.75	3.664 (3)	162
C26—H26···Cg3^iv	0.95	2.68	3.546 (3)	152

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

Funding information

The support of NSF–MRI grant No. 1228232 for the purchase of the diffractometer and Tulane University for support of the Tulane Crystallography Laboratory are gratefully acknowledged.

References

Bruker (2016). APEX3 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Hawaiz, F. E. & Shekh Omer, D. A. (2017). ARO - -The Scientific Journal of Koya University, 5, 30–35. CrossRef Google Scholar
Hussein, A. J. & Azeez, H. J. (2013). J. Chem, 2013, 1–6. Google Scholar
Sheldrick, G. M. (2009). TWINABS. University of Göttingen, Göttingen, Germany. 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
Spek, A. L. (2015). Acta Cryst. C71, 9–18. Web of Science CrossRef IUCr Journals Google Scholar

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Volume 3| Part 2| February 2018| x180251

https://doi.org/10.1107/S2414314618002511

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

Bis(2-formyl­phen­yl) benzene-1,2-di­carboxyl­ate

Structure description

Synthesis and crystallization

Refinement

Structural data

Funding information

References

organic compounds

Bis(2-formylphenyl) benzene-1,2-dicarboxylate