Tetra-methyl 5,5'-[4,5-dicyano-1,2-phenyl-enebis(-oxy)]diisophthalate chloro-form monosolvate.

In the title compound, C(28)H(20)N(2)O(10)·CHCl(3), the phen-oxy 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 inter-molecular C-H⋯O hydrogen bonds link mol-ecules related by an inversion center, forming dimers. There are also C-H⋯π inter-actions 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 = 663.85

Triclinic,

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[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.159

S = 1.08

5257 reflections

397 parameters

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.49 e Å−3

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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811024718/su2272sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536811024718/su2272Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C28H20N2O10·CHCl3	Z = 2
Mr = 663.85	F(000) = 680
Triclinic, P1	Dx = 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

Bruker SMART CCD area-detector diffractometer	3557 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.029
graphite	θmax = 25.0°, θmin = 1.5°
φ and ω scans	h = −11→11
7568 measured reflections	k = −7→13
5257 independent reflections	l = −16→16

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(Fo2) + (0.0657P)2 + 0.6098P] where P = (Fo2 + 2Fc2)/3
5257 reflections	(Δ/σ)max < 0.001
397 parameters	Δρmax = 0.46 e Å−3
0 restraints	Δρmin = −0.49 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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

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

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) ; (ii) ; (iii) .