Dimethyl 4,4′-(di­methyl­silanedi­yl)dibenzoate

Zhang, L.; Xia, Y.; Li, D.; Hou, R.

doi:10.1107/S2414314616018873

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 1| Part 12| December 2016| x161887

https://doi.org/10.1107/S2414314616018873

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Dimethyl 4,4′-(dimethylsilanediyl)dibenzoate

Lingling Zhang,^a Yan Xia,^a Dongfeng Li ^a and Ruibin Hou ^a,^b ^*

^aSchool of Chemistry and Life Science, Changchun University of Technology, Changchun 130012, People's Republic of China, and ^bAdvanced Institute of Materials Science, Changchun University of Technology, Changchun 130012, People's Republic of China
^*Correspondence e-mail: hrb1018@163.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 21 September 2016; accepted 25 November 2016; online 9 December 2016)

The complete molecule of the title compound, C₁₈H₂₀O₄Si, is generated by crystallographic twofold symmetry, with the Si atom lying on the rotation axis. The molecule adopts a V-shape: the dihedral angle between the benzene ring and it attached methyl formate unit is 9.3 (2)°, and the dihedral angle between the benzene rings is 68.8 (1)°. In the crystal, weak C—H⋯O hydrogen bonds link the molecules into [101] chains.

Keywords: crystal structure; organosilicon; C—H⋯O interactions.

CCDC reference: 1519189

Structure description

Recently, several reports have indicated that Si-based tetrahedral organic molecules have excellent emission properties (Li et al., 2015 ; Zhao et al., 2015 ; Shimada et al., 2015 ). As a typical example, Liu and co-workers recently reported a series of tetrahedral luminescent materials comprising SiAr4 cores (Tang et al., 2014 ). They found that their fluorene derivatives were efficient blue-light-emitting materials and that Si-centered materials were superior with regard to film formation ability and quantum efficiency. A noteworthy feature of Si-centered tetrahedral materials is their high photoluminescence efficiency (nearly 100%) in the condensed state. In this paper, we report the crystal structure of the title compound, which is a precursor of these organosilicon compounds.

The complete molecule (Fig. 1) is generated by crystallographic twofold symmetry with the silicon atom lying on the rotation axis. The C—Si—C angles vary from 106.0 (1)° to 112.3 (1)°. The Si—C bond lengths of 1.866 (2) and 1.887 (2) Å are comparable with those in related structures (Ziller et al., 1993 ; Yoshida et al., 2005 ; Tsutsui & Sakamoto, 2003 ). The molecule adopts a V-shape and the dihedral angle between the benzene rings is 68.78 (7)°.

Figure 1
The molecular structure of the title compound.

In the crystal, there are weak C—H⋯O hydrogen bonds (Fig. 2 and Table 1). Atom O2 accepts two such bonds, resulting in an aggregation of three molecules. The trimers are further linked to each other to form a double zigzag chain propagating along the [101] direction.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯O2ⁱ	0.96	2.62	3.511 (2)	154
C9—H9C⋯O2ⁱⁱ	0.96	2.53	3.465 (3)	164
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+2]$ ; (ii) $[-x, y, -z+{\script{3\over 2}}]$ .

Figure 2
The packing of the title compound.

Synthesis and crystallization

The title compound was prepared according to a literature method (Tang et al., 2007 ). Colourless blocks were prepared by recrystallization from a solvent mixture of dichloromethane and petroleum.

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula	C₁₈H₂₀O₄Si
M_r	328.43
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	296
a, b, c (Å)	15.869 (3), 9.991 (2), 12.328 (3)
β (°)	117.79 (3)
V (Å³)	1729.1 (6)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.15
Crystal size (mm)	0.36 × 0.35 × 0.18

Data collection
Diffractometer	Rigaku R-AXIS RAPID CCD
Absorption correction	Multi-scan (RAPID-AUTO; Rigaku, 1998 )
T_min, T_max	0.948, 0.974
No. of measured, independent and observed [I > 2σ(I)] reflections	8251, 1974, 1647
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.130, 1.06
No. of reflections	1974
No. of parameters	107
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.15
Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC and Rigaku, 2002 ), SHELXS97, SHELXL97 and SHELXTL (Sheldrick, 2008 ).

Structural data

CCDC reference: 1519189

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314616018873/hb4082sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314616018873/hb4082Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314616018873/hb4082Isup3.cml

checkCIF report

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC and Rigaku, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Dimethyl 4,4'-(dimethylsilanediyl)dibenzoate top

Crystal data top

C₁₈H₂₀O₄Si	F(000) = 696
M_r = 328.43	D_x = 1.262 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 7030 reflections
a = 15.869 (3) Å	θ = 3.5–27.5°
b = 9.991 (2) Å	µ = 0.15 mm⁻¹
c = 12.328 (3) Å	T = 296 K
β = 117.79 (3)°	Block, colorless
V = 1729.1 (6) Å³	0.36 × 0.35 × 0.18 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID CCD diffractometer	1974 independent reflections
Radiation source: fine-focus sealed tube	1647 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ω scans	θ_max = 27.5°, θ_min = 3.5°
Absorption correction: multi-scan (RAPID-AUTO; Rigaku, 1998)	h = −20→17
T_min = 0.948, T_max = 0.974	k = −12→12
8251 measured reflections	l = −15→16

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.130	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0867P)² + 0.2156P] where P = (F_o² + 2F_c²)/3
1974 reflections	(Δ/σ)_max = 0.010
107 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.15 e Å⁻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. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
C1	0.54323 (13)	0.86561 (16)	1.16029 (15)	0.0529 (4)
H1A	0.4953	0.9300	1.1125	0.079*
H1B	0.5560	0.8090	1.1068	0.079*
H1C	0.6005	0.9113	1.2155	0.079*
C2	0.40084 (10)	0.64788 (13)	1.14363 (12)	0.0378 (3)
C3	0.41296 (11)	0.56740 (17)	1.05964 (16)	0.0522 (4)
H3	0.4702	0.5715	1.0562	0.063*
C4	0.34246 (11)	0.48152 (17)	0.98120 (15)	0.0513 (4)
H4	0.3521	0.4303	0.9249	0.062*
C5	0.25723 (9)	0.47202 (14)	0.98686 (13)	0.0400 (3)
C6	0.24381 (11)	0.54968 (16)	1.07046 (15)	0.0487 (4)
H6	0.1871	0.5434	1.0752	0.058*
C7	0.31455 (11)	0.63684 (16)	1.14723 (14)	0.0470 (4)
H7	0.3042	0.6891	1.2023	0.056*
C8	0.17949 (10)	0.37917 (15)	0.90651 (13)	0.0437 (4)
C9	0.12150 (13)	0.23692 (19)	0.73424 (17)	0.0623 (5)
H9A	0.1119	0.1643	0.7783	0.094*
H9B	0.1401	0.2020	0.6761	0.094*
H9C	0.0633	0.2866	0.6918	0.094*
O1	0.19538 (8)	0.32396 (12)	0.81941 (11)	0.0559 (3)
O2	0.10978 (9)	0.35693 (14)	0.91819 (12)	0.0667 (4)
Si1	0.5000	0.76151 (5)	1.2500	0.0378 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0619 (10)	0.0484 (8)	0.0529 (9)	−0.0023 (7)	0.0306 (8)	0.0075 (7)
C2	0.0385 (7)	0.0404 (7)	0.0336 (6)	0.0032 (5)	0.0160 (5)	0.0029 (5)
C3	0.0419 (8)	0.0650 (10)	0.0570 (9)	−0.0078 (7)	0.0292 (7)	−0.0168 (7)
C4	0.0490 (8)	0.0608 (9)	0.0518 (9)	−0.0065 (7)	0.0301 (7)	−0.0167 (7)
C5	0.0361 (7)	0.0427 (7)	0.0376 (7)	0.0020 (5)	0.0140 (5)	0.0029 (5)
C6	0.0376 (7)	0.0605 (9)	0.0518 (9)	−0.0015 (6)	0.0241 (7)	−0.0045 (7)
C7	0.0466 (8)	0.0536 (8)	0.0454 (8)	0.0013 (6)	0.0253 (7)	−0.0074 (6)
C8	0.0385 (7)	0.0453 (8)	0.0424 (8)	0.0021 (5)	0.0148 (6)	0.0022 (6)
C9	0.0545 (10)	0.0659 (11)	0.0546 (10)	−0.0100 (8)	0.0153 (8)	−0.0173 (8)
O1	0.0473 (6)	0.0658 (7)	0.0525 (7)	−0.0100 (5)	0.0215 (5)	−0.0177 (5)
O2	0.0516 (7)	0.0819 (9)	0.0720 (9)	−0.0195 (6)	0.0333 (6)	−0.0199 (7)
Si1	0.0413 (3)	0.0377 (3)	0.0356 (3)	0.000	0.0188 (2)	0.000

Geometric parameters (Å, º) top

C1—Si1	1.8662 (16)	C5—C8	1.491 (2)
C1—H1A	0.9600	C6—C7	1.387 (2)
C1—H1B	0.9600	C6—H6	0.9300
C1—H1C	0.9600	C7—H7	0.9300
C2—C3	1.393 (2)	C8—O2	1.2009 (19)
C2—C7	1.395 (2)	C8—O1	1.3318 (19)
C2—Si1	1.8869 (15)	C9—O1	1.4440 (19)
C3—C4	1.383 (2)	C9—H9A	0.9600
C3—H3	0.9300	C9—H9B	0.9600
C4—C5	1.390 (2)	C9—H9C	0.9600
C4—H4	0.9300	Si1—C1ⁱ	1.8662 (16)
C5—C6	1.383 (2)	Si1—C2ⁱ	1.8869 (15)

Si1—C1—H1A	109.5	C7—C6—H6	119.9
Si1—C1—H1B	109.5	C6—C7—C2	121.47 (14)
H1A—C1—H1B	109.5	C6—C7—H7	119.3
Si1—C1—H1C	109.5	C2—C7—H7	119.3
H1A—C1—H1C	109.5	O2—C8—O1	123.46 (14)
H1B—C1—H1C	109.5	O2—C8—C5	123.95 (14)
C3—C2—C7	117.11 (13)	O1—C8—C5	112.59 (13)
C3—C2—Si1	120.29 (11)	O1—C9—H9A	109.5
C7—C2—Si1	122.57 (11)	O1—C9—H9B	109.5
C4—C3—C2	122.03 (14)	H9A—C9—H9B	109.5
C4—C3—H3	119.0	O1—C9—H9C	109.5
C2—C3—H3	119.0	H9A—C9—H9C	109.5
C3—C4—C5	119.74 (14)	H9B—C9—H9C	109.5
C3—C4—H4	120.1	C8—O1—C9	116.16 (13)
C5—C4—H4	120.1	C1ⁱ—Si1—C1	112.26 (11)
C6—C5—C4	119.38 (14)	C1ⁱ—Si1—C2	109.23 (7)
C6—C5—C8	118.47 (13)	C1—Si1—C2	109.96 (7)
C4—C5—C8	122.15 (14)	C1ⁱ—Si1—C2ⁱ	109.96 (7)
C5—C6—C7	120.25 (14)	C1—Si1—C2ⁱ	109.23 (7)
C5—C6—H6	119.9	C2—Si1—C2ⁱ	106.02 (9)

C7—C2—C3—C4	1.1 (2)	C4—C5—C8—O2	171.12 (16)
Si1—C2—C3—C4	179.15 (13)	C6—C5—C8—O1	171.45 (13)
C2—C3—C4—C5	−1.3 (3)	C4—C5—C8—O1	−9.3 (2)
C3—C4—C5—C6	0.5 (2)	O2—C8—O1—C9	2.1 (2)
C3—C4—C5—C8	−178.70 (15)	C5—C8—O1—C9	−177.48 (13)
C4—C5—C6—C7	0.5 (2)	C3—C2—Si1—C1ⁱ	174.94 (12)
C8—C5—C6—C7	179.71 (14)	C7—C2—Si1—C1ⁱ	−7.11 (14)
C5—C6—C7—C2	−0.7 (2)	C3—C2—Si1—C1	51.33 (14)
C3—C2—C7—C6	−0.1 (2)	C7—C2—Si1—C1	−130.71 (13)
Si1—C2—C7—C6	−178.09 (12)	C3—C2—Si1—C2ⁱ	−66.63 (12)
C6—C5—C8—O2	−8.1 (2)	C7—C2—Si1—C2ⁱ	111.33 (13)

Symmetry code: (i) −x+1, y, −z+5/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O2ⁱⁱ	0.96	2.62	3.511 (2)	154
C9—H9C···O2ⁱⁱⁱ	0.96	2.53	3.465 (3)	164

Symmetry codes: (ii) −x+1/2, −y+3/2, −z+2; (iii) −x, y, −z+3/2.

Acknowledgements

This work was supported by the National Science Foundation of China (grant No. 21442004) and the Education Office of Jilin Province (grant No. 2016320).

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