Tetra­methyl 5,5′-[4,5-dicyano-1,2-phenyl­enebis(­oxy)]diisophthalate chloro­form monosolvate

Yang, F.; Meng, F.; Zhang, X.; Bai, M.

doi:10.1107/S1600536811024718

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1836

doi:10.1107/S1600536811024718

Open

access

Tetramethyl 5,5′-[4,5-dicyano-1,2-phenylenebis(oxy)]diisophthalate chloroform monosolvate

Fei Yang,^a Fanjun Meng,^a Xiaomei Zhang ^b and Ming Bai ^a ^*

^aMarine College, Shandong University at Weihai, Weihai 264209, People's Republic of China, and ^bSchool of Chemistry & Chemical Technology, Shandong University, Jinan 250100, People's Republic of China
^*Correspondence e-mail: ming_bai@sdu.edu.cn

(Received 5 May 2011; accepted 23 June 2011; online 30 June 2011)

In the title compound, C₂₈H₂₀N₂O₁₀·CHCl₃, the phenoxy rings are inclined to the central phenyl ring at dihedral angles of 84.71 (13) and 80.56 (13)°. In the crystal, pairs of weak intermolecular C—H⋯O hydrogen bonds link molecules related by an inversion center, forming dimers. There are also C—H⋯π interactions present.

Related literature

For general structural and background information on phthalocyanines, including properties and appplications, see: Kobayashi (2001 ); LukCentyanets (1999 ); Suda et al. (2009 ); Zhang et al. (2009 ). For the synthesis of the title compound, see: del Rey et al. (1998 ). For the crystal structure of a similar compound, dimethyl 2,2′-(4,5-dicyano-o-phenylenedioxy)dibenzoate, see: Ocak et al. (2004 ).

Experimental

Crystal data

C₂₈H₂₀N₂O₁₀·CHCl₃
M_r = 663.85
Triclinic, $[P \overline 1]$
a = 9.9223 (13) Å
b = 11.4374 (15) Å
c = 13.9398 (19) Å
α = 96.860 (2)°
β = 94.578 (2)°
γ = 105.326 (2)°
V = 1504.5 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.37 mm⁻¹
T = 298 K
0.15 × 0.12 × 0.05 mm

Data collection

Bruker SMART CCD area-detector diffractometer
7568 measured reflections
5257 independent reflections
3557 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.159
S = 1.08
5257 reflections
397 parameters
H-atom parameters constrained
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.49 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C11–C16 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15⋯O7ⁱ	0.93	2.60	3.455 (4)	154
C29—H29⋯O3ⁱⁱ	0.98	2.26	3.182 (5)	157
C19—H19A⋯Cg2ⁱⁱⁱ	0.98	2.90	3.709 (4)	143
Symmetry codes: (i) -x, -y+1, -z; (ii) -x+1, -y, -z+1; (iii) x-1, y, z.

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus; 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811024718/su2272sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811024718/su2272Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811024718/su2272Isup3.cml

checkCIF report

Comment top

Dicyano compounds have been widely used to synthesize many useful materials such as phthalocyanines. Phthalocyanines are an interesting class of compounds, with increasingly diverse industrial and biomedical applications, for instance as dyes and pigments, materials for optical storage (Kobayashi et al. 2001), photodynamic therapy agents (LukCentyanets et al. 1999), catalysis (Suda et al. 2009), and corrosion inhibitors (Zhang et al. 2009). The title compound was prepared according to the method reported in the literature (del Rey et al., 1998), and its crystal structure is described herein. The crystal structure of a similar compound, Dimethyl 2,2'-(4,5-dicyano-o-phenylenedioxy)dibenzoate, has been described by (Ocak et al., 2004).

The molecular structure of the title compound is shown in Fig. 1. It has a kite-like configuration with the aromatic rings and two cyanide groups being the head and the substituted 3,5-Bismethoxycarbonyl phenoxy groups being the tails. The mean planes of the phenoxy rings [A = (C5-C10) and C = (C23-C28)] are inclinded to the mean plane of the central phenyl ring [B = (C11-C16)], with dihedral angles of A/B = 84.71 (13) ° and C/B = 80.56 (13) °, while planes A and C are inclined to one another by 11.93 (13) °.

In the crystal weak intermolecular C—H···O hydrogen bonds link molecules related by an inversion center to form dimers (Table 1). There is also a C-H···π interaction present in the crystal structure (Table 1).

Related literature top

For general structural and background information on phthalocyanines, including properties and appplications, see: Kobayashi (2001); LukCentyanets (1999); Suda et al. (2009); Zhang et al. (2009). For the synthesis of the title compound, see: del Rey et al. (1998). For the crystal structure of a similar compound, dimethyl 2,2'-(4,5-dicyano-o-phenylenedioxy)dibenzoate, see: Ocak et al. (2004).

Experimental top

The title compound was prepared according to a published procedure (del Rey et al., 1998). Colourless block-like crystals, suitable for X-ray diffraction analysis, were obtained by slow evaporation of a solution of the title compound in chloroform.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus (Bruker, 2007); 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: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. A view of the molecular structure of the title compound with the atom labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.

Tetramethyl 5,5'-[4,5-dicyano-1,2-phenylenebis(oxy)]diisophthalate chloroform monosolvate top

Crystal data top

C₂₈H₂₀N₂O₁₀·CHCl₃	Z = 2
M_r = 663.85	F(000) = 680
Triclinic, P1	D_x = 1.465 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.9223 (13) Å	Cell parameters from 1932 reflections
b = 11.4374 (15) Å	θ = 2.7–23.6°
c = 13.9398 (19) Å	µ = 0.37 mm⁻¹
α = 96.860 (2)°	T = 298 K
β = 94.578 (2)°	Block, colourless
γ = 105.326 (2)°	0.15 × 0.12 × 0.05 mm
V = 1504.5 (3) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	3557 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.029
Graphite monochromator	θ_max = 25.0°, θ_min = 1.5°
ϕ and ω scans	h = −11→11
7568 measured reflections	k = −7→13
5257 independent reflections	l = −16→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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.159	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0657P)² + 0.6098P] where P = (F_o² + 2F_c²)/3
5257 reflections	(Δ/σ)_max < 0.001
397 parameters	Δρ_max = 0.46 e Å⁻³
0 restraints	Δρ_min = −0.49 e Å⁻³

Crystal data top

C₂₈H₂₀N₂O₁₀·CHCl₃	γ = 105.326 (2)°
M_r = 663.85	V = 1504.5 (3) Å³
Triclinic, P1	Z = 2
a = 9.9223 (13) Å	Mo Kα radiation
b = 11.4374 (15) Å	µ = 0.37 mm⁻¹
c = 13.9398 (19) Å	T = 298 K
α = 96.860 (2)°	0.15 × 0.12 × 0.05 mm
β = 94.578 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3557 reflections with I > 2σ(I)
7568 measured reflections	R_int = 0.029
5257 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.159	H-atom parameters constrained
S = 1.08	Δρ_max = 0.46 e Å⁻³
5257 reflections	Δρ_min = −0.49 e Å⁻³
397 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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
Cl1	0.33835 (13)	0.52563 (10)	0.60702 (9)	0.0890 (4)
Cl2	0.27318 (15)	0.33393 (13)	0.44608 (10)	0.1086 (5)
Cl3	0.25891 (16)	0.27612 (12)	0.63996 (12)	0.1147 (5)
O1	0.0551 (2)	0.25073 (18)	0.19677 (15)	0.0442 (5)
O2	0.2198 (2)	0.12734 (18)	0.26465 (14)	0.0449 (5)
O3	0.3694 (3)	−0.2971 (3)	0.4139 (3)	0.0968 (11)
O4	0.1564 (2)	−0.2758 (2)	0.37967 (19)	0.0617 (6)
O5	0.7479 (3)	0.2270 (2)	0.3509 (2)	0.0726 (7)
O6	0.7752 (2)	0.0552 (2)	0.39934 (19)	0.0641 (7)
O7	0.2002 (2)	0.7618 (2)	0.09592 (19)	0.0631 (7)
O8	0.3489 (2)	0.6556 (2)	0.1366 (2)	0.0668 (7)
O9	−0.3096 (2)	0.5709 (2)	0.0965 (2)	0.0718 (8)
O10	−0.3797 (2)	0.3866 (2)	0.14128 (19)	0.0609 (7)
N1	0.0918 (4)	0.1109 (3)	−0.2174 (2)	0.0726 (9)
N2	0.3628 (4)	−0.0670 (3)	−0.1112 (2)	0.0697 (9)
C1	0.0951 (4)	−0.3963 (3)	0.4050 (3)	0.0742 (11)
H1A	−0.0057	−0.4147	0.3956	0.111*
H1B	0.1255	−0.3975	0.4719	0.111*
H1C	0.1247	−0.4564	0.3643	0.111*
C2	0.2951 (4)	−0.2372 (3)	0.3889 (2)	0.0520 (8)
C3	0.9268 (4)	0.1075 (4)	0.4124 (3)	0.0765 (12)
H3A	0.9712	0.0493	0.4353	0.115*
H3B	0.9512	0.1807	0.4591	0.115*
H3C	0.9584	0.1269	0.3514	0.115*
C4	0.6988 (3)	0.1245 (3)	0.3676 (2)	0.0480 (8)
C5	0.5452 (3)	0.0611 (3)	0.3552 (2)	0.0423 (7)
C6	0.4918 (3)	−0.0554 (3)	0.3781 (2)	0.0427 (7)
H6	0.5526	−0.0971	0.4026	0.051*
C7	0.3471 (3)	−0.1105 (3)	0.3645 (2)	0.0406 (7)
C8	0.2562 (3)	−0.0503 (3)	0.3263 (2)	0.0414 (7)
H8	0.1597	−0.0868	0.3163	0.050*
C9	0.3125 (3)	0.0655 (3)	0.3032 (2)	0.0405 (7)
C10	0.4542 (3)	0.1227 (3)	0.3169 (2)	0.0440 (7)
H10	0.4889	0.2009	0.3009	0.053*
C11	0.1995 (3)	0.1196 (2)	0.1661 (2)	0.0344 (6)
C12	0.2607 (3)	0.0520 (2)	0.1030 (2)	0.0383 (7)
H12	0.3180	0.0072	0.1272	0.046*
C13	0.2363 (3)	0.0511 (2)	0.0030 (2)	0.0370 (7)
C14	0.1470 (3)	0.1163 (2)	−0.0330 (2)	0.0388 (7)
C15	0.0845 (3)	0.1825 (2)	0.0309 (2)	0.0390 (7)
H15	0.0235	0.2243	0.0069	0.047*
C16	0.1129 (3)	0.1864 (2)	0.1303 (2)	0.0334 (6)
C17	0.3050 (3)	−0.0161 (3)	−0.0612 (2)	0.0461 (8)
C18	0.1171 (3)	0.1129 (3)	−0.1363 (3)	0.0475 (8)
C19	−0.5227 (3)	0.3945 (4)	0.1327 (4)	0.0805 (13)
H19A	−0.5841	0.3203	0.1474	0.121*
H19B	−0.5497	0.4057	0.0675	0.121*
H19C	−0.5296	0.4627	0.1774	0.121*
C20	−0.2831 (3)	0.4828 (3)	0.1232 (2)	0.0460 (8)
C21	0.4657 (4)	0.7573 (3)	0.1234 (3)	0.0764 (12)
H21A	0.5525	0.7368	0.1364	0.115*
H21B	0.4659	0.8286	0.1674	0.115*
H21C	0.4560	0.7738	0.0576	0.115*
C22	0.2215 (3)	0.6710 (3)	0.1206 (2)	0.0444 (7)
C23	0.1085 (3)	0.5622 (3)	0.1353 (2)	0.0383 (7)
C24	0.1361 (3)	0.4546 (3)	0.1580 (2)	0.0423 (7)
H24	0.2280	0.4489	0.1648	0.051*
C25	0.0262 (3)	0.3570 (2)	0.1704 (2)	0.0369 (7)
C26	−0.1108 (3)	0.3622 (2)	0.1620 (2)	0.0378 (7)
H26	−0.1836	0.2959	0.1717	0.045*
C27	−0.1380 (3)	0.4696 (2)	0.1384 (2)	0.0368 (6)
C28	−0.0290 (3)	0.5684 (2)	0.1264 (2)	0.0388 (7)
H28	−0.0484	0.6401	0.1121	0.047*
C29	0.3476 (4)	0.3780 (3)	0.5670 (3)	0.0693 (10)
H29	0.4465	0.3775	0.5714	0.083*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1033 (9)	0.0602 (6)	0.0974 (8)	0.0206 (6)	−0.0056 (7)	0.0035 (6)
Cl2	0.1101 (10)	0.1139 (10)	0.0909 (9)	0.0277 (8)	0.0109 (7)	−0.0198 (7)
Cl3	0.1220 (11)	0.0944 (9)	0.1517 (13)	0.0433 (8)	0.0374 (10)	0.0686 (9)
O1	0.0507 (12)	0.0411 (11)	0.0573 (13)	0.0295 (10)	0.0204 (10)	0.0252 (10)
O2	0.0547 (13)	0.0479 (12)	0.0438 (12)	0.0335 (10)	0.0024 (10)	0.0111 (9)
O3	0.0627 (17)	0.084 (2)	0.172 (3)	0.0375 (16)	0.0266 (19)	0.082 (2)
O4	0.0492 (14)	0.0522 (14)	0.0856 (17)	0.0126 (11)	−0.0005 (12)	0.0264 (12)
O5	0.0580 (16)	0.0530 (16)	0.105 (2)	0.0099 (12)	0.0025 (14)	0.0214 (15)
O6	0.0420 (13)	0.0696 (16)	0.0866 (18)	0.0209 (12)	0.0016 (12)	0.0266 (13)
O7	0.0543 (14)	0.0385 (13)	0.103 (2)	0.0147 (11)	0.0114 (13)	0.0288 (13)
O8	0.0338 (12)	0.0472 (13)	0.126 (2)	0.0116 (10)	0.0160 (13)	0.0335 (14)
O9	0.0484 (14)	0.0574 (15)	0.122 (2)	0.0277 (12)	0.0034 (14)	0.0368 (15)
O10	0.0321 (12)	0.0536 (14)	0.1036 (19)	0.0167 (10)	0.0065 (12)	0.0268 (13)
N1	0.082 (2)	0.080 (2)	0.054 (2)	0.0174 (18)	−0.0012 (17)	0.0185 (17)
N2	0.086 (2)	0.0566 (19)	0.071 (2)	0.0247 (17)	0.0272 (18)	0.0006 (16)
C1	0.070 (3)	0.056 (2)	0.095 (3)	0.0055 (19)	0.008 (2)	0.031 (2)
C2	0.053 (2)	0.052 (2)	0.060 (2)	0.0240 (17)	0.0074 (16)	0.0210 (16)
C3	0.039 (2)	0.095 (3)	0.097 (3)	0.024 (2)	0.0019 (19)	0.015 (2)
C4	0.0483 (19)	0.054 (2)	0.0447 (18)	0.0195 (16)	0.0031 (14)	0.0065 (15)
C5	0.0466 (18)	0.0496 (18)	0.0354 (16)	0.0211 (14)	0.0027 (13)	0.0076 (13)
C6	0.0463 (18)	0.0498 (18)	0.0391 (17)	0.0234 (14)	0.0016 (13)	0.0140 (14)
C7	0.0435 (17)	0.0455 (17)	0.0384 (16)	0.0203 (14)	0.0013 (13)	0.0121 (13)
C8	0.0399 (16)	0.0476 (18)	0.0424 (17)	0.0208 (14)	0.0026 (13)	0.0104 (14)
C9	0.0484 (18)	0.0467 (18)	0.0356 (16)	0.0282 (14)	0.0029 (13)	0.0100 (13)
C10	0.0507 (19)	0.0427 (17)	0.0421 (17)	0.0190 (14)	0.0020 (14)	0.0087 (13)
C11	0.0367 (15)	0.0290 (14)	0.0402 (16)	0.0120 (12)	0.0027 (12)	0.0109 (12)
C12	0.0387 (16)	0.0300 (15)	0.0505 (18)	0.0163 (12)	0.0004 (13)	0.0109 (13)
C13	0.0371 (15)	0.0272 (14)	0.0470 (18)	0.0087 (12)	0.0040 (13)	0.0074 (12)
C14	0.0389 (16)	0.0318 (15)	0.0446 (17)	0.0054 (12)	0.0005 (13)	0.0135 (13)
C15	0.0356 (15)	0.0354 (15)	0.0513 (18)	0.0135 (13)	0.0029 (13)	0.0195 (13)
C16	0.0283 (14)	0.0265 (14)	0.0493 (18)	0.0101 (11)	0.0082 (12)	0.0127 (12)
C17	0.0505 (19)	0.0365 (17)	0.0507 (19)	0.0117 (14)	0.0047 (15)	0.0058 (14)
C18	0.0485 (19)	0.0425 (18)	0.052 (2)	0.0108 (14)	0.0024 (15)	0.0151 (15)
C19	0.0315 (19)	0.082 (3)	0.135 (4)	0.0209 (18)	0.005 (2)	0.037 (3)
C20	0.0372 (17)	0.0388 (17)	0.065 (2)	0.0164 (14)	0.0021 (15)	0.0103 (15)
C21	0.042 (2)	0.054 (2)	0.133 (4)	0.0035 (17)	0.024 (2)	0.024 (2)
C22	0.0426 (17)	0.0368 (17)	0.058 (2)	0.0137 (14)	0.0111 (14)	0.0116 (14)
C23	0.0390 (16)	0.0352 (15)	0.0458 (17)	0.0151 (13)	0.0076 (13)	0.0129 (13)
C24	0.0336 (16)	0.0441 (17)	0.0582 (19)	0.0209 (13)	0.0106 (14)	0.0159 (14)
C25	0.0403 (16)	0.0339 (15)	0.0460 (17)	0.0209 (13)	0.0110 (13)	0.0159 (13)
C26	0.0354 (15)	0.0314 (15)	0.0501 (18)	0.0126 (12)	0.0073 (13)	0.0114 (13)
C27	0.0347 (15)	0.0357 (15)	0.0444 (17)	0.0163 (12)	0.0035 (12)	0.0089 (13)
C28	0.0411 (17)	0.0316 (15)	0.0508 (18)	0.0196 (13)	0.0047 (13)	0.0126 (13)
C29	0.061 (2)	0.068 (2)	0.087 (3)	0.028 (2)	0.011 (2)	0.018 (2)

Geometric parameters (Å, º) top

Cl1—C29	1.743 (4)	C7—C8	1.383 (4)
Cl2—C29	1.744 (4)	C8—C9	1.381 (4)
Cl3—C29	1.747 (4)	C8—H8	0.9300
O1—C16	1.369 (3)	C9—C10	1.372 (4)
O1—C25	1.403 (3)	C10—H10	0.9300
O2—C11	1.362 (3)	C11—C12	1.383 (4)
O2—C9	1.411 (3)	C11—C16	1.392 (4)
O3—C2	1.191 (4)	C12—C13	1.394 (4)
O4—C2	1.320 (4)	C12—H12	0.9300
O4—C1	1.449 (4)	C13—C14	1.400 (4)
O5—C4	1.203 (4)	C13—C17	1.438 (4)
O6—C4	1.322 (4)	C14—C15	1.389 (4)
O6—C3	1.452 (4)	C14—C18	1.440 (4)
O7—C22	1.196 (4)	C15—C16	1.385 (4)
O8—C22	1.327 (4)	C15—H15	0.9300
O8—C21	1.450 (4)	C19—H19A	0.9600
O9—C20	1.199 (4)	C19—H19B	0.9600
O10—C20	1.320 (4)	C19—H19C	0.9600
O10—C19	1.442 (4)	C20—C27	1.488 (4)
N1—C18	1.135 (4)	C21—H21A	0.9600
N2—C17	1.139 (4)	C21—H21B	0.9600
C1—H1A	0.9600	C21—H21C	0.9600
C1—H1B	0.9600	C22—C23	1.486 (4)
C1—H1C	0.9600	C23—C28	1.382 (4)
C2—C7	1.493 (4)	C23—C24	1.395 (4)
C3—H3A	0.9600	C24—C25	1.377 (4)
C3—H3B	0.9600	C24—H24	0.9300
C3—H3C	0.9600	C25—C26	1.373 (4)
C4—C5	1.492 (4)	C26—C27	1.396 (4)
C5—C6	1.383 (4)	C26—H26	0.9300
C5—C10	1.395 (4)	C27—C28	1.379 (4)
C6—C7	1.395 (4)	C28—H28	0.9300
C6—H6	0.9300	C29—H29	0.9800

C16—O1—C25	116.6 (2)	C15—C14—C18	119.7 (3)
C11—O2—C9	117.2 (2)	C13—C14—C18	120.3 (3)
C2—O4—C1	116.7 (3)	C16—C15—C14	120.0 (3)
C4—O6—C3	116.7 (3)	C16—C15—H15	120.0
C22—O8—C21	116.1 (3)	C14—C15—H15	120.0
C20—O10—C19	116.2 (3)	O1—C16—C15	122.6 (2)
O4—C1—H1A	109.5	O1—C16—C11	117.3 (2)
O4—C1—H1B	109.5	C15—C16—C11	120.0 (3)
H1A—C1—H1B	109.5	N2—C17—C13	178.1 (4)
O4—C1—H1C	109.5	N1—C18—C14	178.9 (4)
H1A—C1—H1C	109.5	O10—C19—H19A	109.5
H1B—C1—H1C	109.5	O10—C19—H19B	109.5
O3—C2—O4	123.5 (3)	H19A—C19—H19B	109.5
O3—C2—C7	124.3 (3)	O10—C19—H19C	109.5
O4—C2—C7	112.3 (3)	H19A—C19—H19C	109.5
O6—C3—H3A	109.5	H19B—C19—H19C	109.5
O6—C3—H3B	109.5	O9—C20—O10	123.5 (3)
H3A—C3—H3B	109.5	O9—C20—C27	123.7 (3)
O6—C3—H3C	109.5	O10—C20—C27	112.8 (2)
H3A—C3—H3C	109.5	O8—C21—H21A	109.5
H3B—C3—H3C	109.5	O8—C21—H21B	109.5
O5—C4—O6	123.8 (3)	H21A—C21—H21B	109.5
O5—C4—C5	124.0 (3)	O8—C21—H21C	109.5
O6—C4—C5	112.2 (3)	H21A—C21—H21C	109.5
C6—C5—C10	119.9 (3)	H21B—C21—H21C	109.5
C6—C5—C4	122.6 (3)	O7—C22—O8	123.6 (3)
C10—C5—C4	117.4 (3)	O7—C22—C23	123.9 (3)
C5—C6—C7	120.1 (3)	O8—C22—C23	112.4 (2)
C5—C6—H6	119.9	C28—C23—C24	119.0 (3)
C7—C6—H6	119.9	C28—C23—C22	118.5 (2)
C8—C7—C6	120.3 (3)	C24—C23—C22	122.6 (3)
C8—C7—C2	121.6 (3)	C25—C24—C23	119.5 (3)
C6—C7—C2	118.0 (3)	C25—C24—H24	120.2
C9—C8—C7	118.3 (3)	C23—C24—H24	120.2
C9—C8—H8	120.8	C26—C25—C24	122.1 (2)
C7—C8—H8	120.8	C26—C25—O1	118.6 (2)
C10—C9—C8	122.7 (3)	C24—C25—O1	119.2 (2)
C10—C9—O2	118.9 (3)	C25—C26—C27	118.2 (3)
C8—C9—O2	118.4 (3)	C25—C26—H26	120.9
C9—C10—C5	118.6 (3)	C27—C26—H26	120.9
C9—C10—H10	120.7	C28—C27—C26	120.5 (3)
C5—C10—H10	120.7	C28—C27—C20	117.0 (2)
O2—C11—C12	123.7 (2)	C26—C27—C20	122.5 (3)
O2—C11—C16	116.0 (2)	C27—C28—C23	120.8 (2)
C12—C11—C16	120.3 (3)	C27—C28—H28	119.6
C11—C12—C13	119.9 (2)	C23—C28—H28	119.6
C11—C12—H12	120.0	Cl1—C29—Cl2	109.5 (2)
C13—C12—H12	120.0	Cl1—C29—Cl3	109.9 (2)
C12—C13—C14	119.7 (3)	Cl2—C29—Cl3	110.2 (2)
C12—C13—C17	119.1 (3)	Cl1—C29—H29	109.1
C14—C13—C17	121.2 (3)	Cl2—C29—H29	109.1
C15—C14—C13	120.0 (3)	Cl3—C29—H29	109.1

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C11–C16 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···O7ⁱ	0.93	2.60	3.455 (4)	154
C29—H29···O3ⁱⁱ	0.98	2.26	3.182 (5)	157
C19—H19A···Cg2ⁱⁱⁱ	0.98	2.90	3.709 (4)	143

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

Experimental details

Crystal data
Chemical formula	C₂₈H₂₀N₂O₁₀·CHCl₃
M_r	663.85
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	9.9223 (13), 11.4374 (15), 13.9398 (19)
α, β, γ (°)	96.860 (2), 94.578 (2), 105.326 (2)
V (Å³)	1504.5 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.37
Crystal size (mm)	0.15 × 0.12 × 0.05

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	7568, 5257, 3557
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.159, 1.08
No. of reflections	5257
No. of parameters	397
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.46, −0.49

Computer programs: SMART (Bruker, 2007), SAINT-Plus (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C11–C16 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···O7ⁱ	0.93	2.60	3.455 (4)	154
C29—H29···O3ⁱⁱ	0.98	2.26	3.182 (5)	157
C19—H19A···Cg2ⁱⁱⁱ	0.98	2.90	3.709 (4)	143

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

Acknowledgements

This work was supported by the Independent Innovation Foundation of Shandong University, IIFSDU.

References

Bruker (2007). APEX2 and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Kobayashi, N. (2001). Coord. Chem. Rev. 219–221, 99–103. CrossRef CAS Google Scholar
LukCentyanets, E. A. (1999). J. Porphyrins Phthalocyanines, 3, 424–432. Google Scholar
Ocak, N., Büyükgüngör, O., Akdemir, N., Ağar, E., Özil, M. & Erdönmez, A. (2004). Acta Cryst. E60, o505–o507. Web of Science CSD CrossRef IUCr Journals Google Scholar
Rey, B. del, Keller, U., Torres, T., Rojo, G., Agulló-López, F., Nonell, S., Martí, C., Brasselet, S., Ledoux, I. & Zyss, J. (1998). J. Am. Chem. Soc. 120, 12808–12817. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Suda, K., Nakajima, S., Satoh, Y. & Takanami, T. (2009). Chem. Commun. pp. 1255–1227. CrossRef Google Scholar
Zhang, X., Wang, W., Jiang, J. & Ni, Z. (2009). Acta Cryst. E65, o837. Web of Science CSD CrossRef IUCr Journals 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 67| Part 7| July 2011| Page o1836

doi:10.1107/S1600536811024718

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

Tetra­methyl 5,5′-[4,5-di­cyano-1,2-phenyl­enebis(­­oxy)]diisophthalate chloro­form monosolvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Tetramethyl 5,5′-[4,5-dicyano-1,2-phenylenebis(oxy)]diisophthalate chloroform monosolvate