4,4′-[2,2-Methyl­enebis(4-chloro­phenoxy)]­diphthalo­nitrile

Çoruh, U.; Işık, Ş.; Akdemir, N.; Ag~ar, E.; Vázquez-López, E.M.; Erdönmez, A.

doi:10.1107/S1600536802013491

4,4′-[2,2-Methylenebis(4-chlorophenoxy)]diphthalonitrile

U. Çoruh, S. Işık, N. Akdemir, E. Agar, E. M. Vázquez-López and A. Erdönmez

The title compound, C₂₉H₁₄Cl₂N₄O₂, (I), contains four phenyl rings. Two of these carry two cyano groups each, whereas the other two carry one Cl atom each. The structure involves four planar phenyl rings. The structure of (I) is stabilized by C—H

N-type intermolecular close contacts.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802013491/bt6171sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536802013491/bt6171Isup2.hkl Contains datablock I

CCDC reference: 193787

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R factor = 0.047
wR factor = 0.104
Data-to-parameter ratio = 14.9

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



PLAT_371  Alert C Long   C(sp2)-C(sp1) Bond  C(1)   -   C(5)   =       1.44 Ang.

PLAT_371  Alert C Long   C(sp2)-C(sp1) Bond  C(1')  -   C(5')  =       1.44 Ang.

PLAT_371  Alert C Long   C(sp2)-C(sp1) Bond  C(2)   -   C(6)   =       1.43 Ang.

PLAT_371  Alert C Long   C(sp2)-C(sp1) Bond  C(2')  -   C(6')  =       1.43 Ang.


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 4 Alert Level C = Please check

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Farrugia, 1997); software used to prepare material for publication: PARST (Nardelli, 1995).

4,4'-[2,2-methylenebis(4-chlorophenoxy)]diphthalonitrile top

Crystal data top

C₂₉H₁₄Cl₂N₄O₂	Z = 2
M_r = 521.34	F(000) = 532
Triclinic, P1	D_x = 1.403 Mg m⁻³
a = 8.3572 (9) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.1209 (13) Å	Cell parameters from 7156 reflections
c = 12.5925 (13) Å	θ = 1.7–26.1°
α = 76.912 (2)°	µ = 0.30 mm⁻¹
β = 84.302 (2)°	T = 293 K
γ = 85.681 (2)°	Prism, colourless
V = 1234.5 (2) Å³	0.26 × 0.18 × 0.10 mm

Data collection top

Bruker CCD area-detector diffractometer	2451 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.027
Graphite monochromator	θ_max = 26.0°, θ_min = 1.7°
φ and ω scans	h = −11→10
7156 measured reflections	k = −15→15
4969 independent reflections	l = −12→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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.104	H-atom parameters constrained
S = 0.83	w = 1/[σ²(F_o²) + (0.0416P)²] where P = (F_o² + 2F_c²)/3
4969 reflections	(Δ/σ)_max < 0.001
334 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

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
Cl'	0.07649 (9)	0.83550 (5)	0.88151 (6)	0.0731 (3)
Cl	−0.31120 (11)	1.63056 (6)	0.55001 (8)	0.1041 (3)
O1'	0.0786 (2)	1.32793 (13)	0.72180 (14)	0.0588 (5)
O1	−0.37253 (19)	1.15562 (13)	0.77856 (14)	0.0583 (5)
C12'	0.0718 (3)	0.98204 (19)	0.8368 (2)	0.0478 (6)
C6	−0.6184 (3)	1.02588 (19)	0.6191 (2)	0.0444 (6)
C8	−0.4494 (3)	1.07922 (19)	0.7384 (2)	0.0459 (6)
C9	−0.3640 (3)	1.26809 (18)	0.7169 (2)	0.0478 (6)
C5	−0.6016 (3)	0.91203 (19)	0.6755 (2)	0.0470 (6)
C6'	−0.1829 (3)	1.45322 (19)	0.9201 (2)	0.0470 (6)
C3	−0.4339 (3)	0.9675 (2)	0.7957 (2)	0.0532 (7)
H3	−0.3725	0.9483	0.8555	0.064*
C14'	−0.0165 (3)	1.1502 (2)	0.7101 (2)	0.0442 (6)
C13'	−0.0116 (3)	1.0323 (2)	0.7488 (2)	0.0481 (6)
H13'	−0.0655	0.9878	0.7143	0.058*
C14	−0.2367 (3)	1.29466 (19)	0.6388 (2)	0.0473 (6)
C5'	−0.1551 (3)	1.5672 (2)	0.8786 (2)	0.0518 (7)
C4	−0.5097 (3)	0.88505 (19)	0.7638 (2)	0.0556 (7)
H4	−0.4989	0.8101	0.8023	0.067*
C8'	0.0010 (3)	1.4026 (2)	0.7796 (2)	0.0498 (7)
C9'	0.0685 (3)	1.2104 (2)	0.7651 (2)	0.0470 (6)
C2'	−0.2908 (4)	1.4216 (2)	1.0161 (3)	0.0595 (8)
C7	−0.5408 (3)	1.10875 (19)	0.6508 (2)	0.0455 (6)
H7	−0.5508	1.1839	0.6129	0.055*
C11'	0.1534 (3)	1.0435 (2)	0.8906 (2)	0.0550 (7)
H11'	0.2083	1.0079	0.9509	0.066*
C7'	−0.1056 (3)	1.37047 (19)	0.8701 (2)	0.0475 (6)
H7'	−0.1256	1.2944	0.8974	0.057*
C4'	−0.0473 (4)	1.5971 (2)	0.7880 (3)	0.0668 (8)
H4'	−0.0282	1.6732	0.7597	0.080*
C13	−0.2275 (3)	1.4078 (2)	0.5860 (2)	0.0560 (7)
H13	−0.1455	1.4288	0.5311	0.067*
C1	−0.6808 (3)	0.8247 (2)	0.6438 (2)	0.0598 (7)
C12	−0.3366 (3)	1.4890 (2)	0.6129 (3)	0.0606 (8)
C10'	0.1520 (3)	1.1602 (2)	0.8528 (2)	0.0554 (7)
H10'	0.2077	1.2040	0.8871	0.066*
C3'	0.0326 (3)	1.5155 (2)	0.7387 (2)	0.0635 (8)
H3'	0.1068	1.5362	0.6787	0.076*
C1'	−0.2387 (3)	1.6519 (2)	0.9301 (2)	0.0581 (7)
C2	−0.7170 (3)	1.0556 (2)	0.5287 (3)	0.0524 (7)
N2	−0.7964 (3)	1.0791 (2)	0.4574 (2)	0.0728 (7)
N1'	−0.3064 (3)	1.71836 (19)	0.9719 (2)	0.0760 (7)
C10	−0.4748 (3)	1.3490 (2)	0.7449 (2)	0.0625 (8)
H10	−0.5582	1.3282	0.7988	0.075*
C15	−0.1097 (3)	1.20588 (19)	0.6145 (2)	0.0536 (7)
H15A	−0.1614	1.1479	0.5904	0.064*
H15B	−0.0349	1.2412	0.5547	0.064*
C11	−0.4607 (3)	1.4612 (2)	0.6920 (3)	0.0674 (8)
H11	−0.5343	1.5170	0.7097	0.081*
N1	−0.7419 (3)	0.75420 (19)	0.6207 (2)	0.0840 (8)
N2'	−0.3741 (3)	1.3969 (2)	1.0951 (2)	0.0824 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl'	0.0957 (5)	0.0478 (4)	0.0698 (5)	−0.0016 (4)	0.0015 (5)	−0.0048 (4)
Cl	0.1206 (7)	0.0428 (4)	0.1353 (8)	−0.0026 (4)	−0.0172 (6)	0.0112 (5)
O1'	0.0723 (11)	0.0490 (11)	0.0552 (12)	−0.0145 (9)	0.0128 (10)	−0.0156 (9)
O1	0.0672 (11)	0.0442 (10)	0.0627 (12)	−0.0117 (8)	−0.0151 (10)	−0.0036 (9)
C12'	0.0499 (14)	0.0467 (15)	0.0457 (17)	0.0003 (12)	0.0060 (14)	−0.0132 (13)
C6	0.0404 (13)	0.0435 (15)	0.0475 (17)	−0.0004 (11)	0.0041 (14)	−0.0104 (12)
C8	0.0410 (13)	0.0400 (14)	0.0552 (18)	−0.0045 (11)	0.0011 (14)	−0.0086 (13)
C9	0.0549 (15)	0.0344 (14)	0.0548 (18)	−0.0063 (12)	−0.0076 (15)	−0.0088 (12)
C5	0.0469 (14)	0.0396 (14)	0.0524 (18)	−0.0058 (12)	0.0044 (14)	−0.0082 (13)
C6'	0.0523 (15)	0.0438 (15)	0.0451 (17)	−0.0057 (12)	−0.0060 (14)	−0.0084 (12)
C3	0.0533 (15)	0.0463 (15)	0.0553 (18)	−0.0014 (12)	−0.0084 (15)	−0.0004 (13)
C14'	0.0436 (14)	0.0498 (15)	0.0418 (16)	0.0037 (12)	−0.0004 (13)	−0.0188 (12)
C13'	0.0491 (14)	0.0487 (16)	0.0506 (17)	−0.0028 (12)	0.0010 (14)	−0.0215 (13)
C14	0.0541 (15)	0.0421 (15)	0.0468 (17)	−0.0013 (12)	−0.0064 (14)	−0.0117 (12)
C5'	0.0620 (16)	0.0423 (15)	0.0546 (18)	−0.0097 (13)	−0.0076 (16)	−0.0146 (13)
C4	0.0558 (16)	0.0363 (14)	0.068 (2)	−0.0055 (12)	0.0027 (16)	−0.0006 (13)
C8'	0.0589 (16)	0.0439 (15)	0.0499 (17)	−0.0133 (13)	0.0032 (15)	−0.0170 (13)
C9'	0.0495 (15)	0.0478 (15)	0.0456 (17)	−0.0052 (12)	0.0053 (14)	−0.0171 (13)
C2'	0.0642 (18)	0.0464 (16)	0.066 (2)	0.0040 (14)	−0.0037 (18)	−0.0118 (15)
C7	0.0442 (13)	0.0353 (13)	0.0540 (17)	−0.0021 (11)	−0.0009 (14)	−0.0051 (12)
C11'	0.0528 (15)	0.0640 (18)	0.0475 (17)	0.0018 (13)	−0.0029 (14)	−0.0132 (14)
C7'	0.0557 (15)	0.0370 (14)	0.0499 (17)	−0.0074 (12)	−0.0059 (15)	−0.0072 (12)
C4'	0.093 (2)	0.0405 (15)	0.070 (2)	−0.0215 (15)	0.0002 (19)	−0.0153 (15)
C13	0.0640 (17)	0.0475 (16)	0.0535 (18)	−0.0049 (14)	−0.0021 (15)	−0.0055 (13)
C1	0.0685 (17)	0.0503 (17)	0.059 (2)	−0.0107 (14)	0.0034 (16)	−0.0094 (14)
C12	0.0670 (18)	0.0395 (15)	0.074 (2)	−0.0023 (14)	−0.0120 (18)	−0.0065 (14)
C10'	0.0498 (15)	0.0647 (19)	0.0588 (19)	−0.0115 (13)	0.0003 (15)	−0.0279 (15)
C3'	0.0818 (19)	0.0523 (17)	0.0568 (19)	−0.0240 (15)	0.0128 (17)	−0.0146 (15)
C1'	0.0674 (18)	0.0450 (16)	0.066 (2)	−0.0085 (14)	−0.0114 (17)	−0.0173 (15)
C2	0.0528 (17)	0.0500 (16)	0.0549 (19)	−0.0062 (13)	0.0026 (17)	−0.0147 (14)
N2	0.0734 (16)	0.0769 (18)	0.0694 (19)	−0.0039 (14)	−0.0105 (16)	−0.0168 (14)
N1'	0.0878 (17)	0.0618 (16)	0.087 (2)	0.0005 (14)	−0.0160 (16)	−0.0321 (15)
C10	0.0477 (15)	0.0582 (18)	0.081 (2)	−0.0067 (14)	0.0046 (16)	−0.0177 (16)
C15	0.0598 (16)	0.0529 (16)	0.0494 (17)	0.0044 (13)	−0.0048 (15)	−0.0159 (13)
C11	0.0636 (18)	0.0452 (17)	0.096 (3)	0.0081 (14)	−0.0118 (19)	−0.0227 (16)
N1	0.115 (2)	0.0612 (16)	0.0785 (19)	−0.0255 (15)	−0.0114 (17)	−0.0125 (14)
N2'	0.0884 (19)	0.0709 (17)	0.082 (2)	0.0006 (14)	0.0103 (17)	−0.0127 (15)

Geometric parameters (Å, º) top

Cl'—C12'	1.736 (2)	C3—C4	1.373 (3)
Cl—C12	1.738 (3)	C14'—C9'	1.385 (3)
O1'—C8'	1.373 (3)	C14'—C13'	1.400 (3)
O1'—C9'	1.411 (3)	C14'—C15	1.500 (3)
O1—C8	1.376 (3)	C14—C13	1.386 (3)
O1—C9	1.411 (3)	C14—C15	1.514 (3)
C12'—C13'	1.367 (3)	C5'—C4'	1.379 (3)
C12'—C11'	1.370 (3)	C5'—C1'	1.437 (3)
C6—C7	1.386 (3)	C8'—C7'	1.376 (3)
C6—C5	1.405 (3)	C8'—C3'	1.385 (3)
C6—C2	1.435 (4)	C9'—C10'	1.366 (3)
C8—C7	1.369 (3)	C2'—N2'	1.150 (3)
C8—C3	1.386 (3)	C11'—C10'	1.386 (3)
C9—C10	1.377 (3)	C4'—C3'	1.380 (3)
C9—C14	1.380 (3)	C13—C12	1.368 (3)
C5—C4	1.379 (3)	C1—N1	1.133 (3)
C5—C1	1.438 (3)	C12—C11	1.370 (4)
C6'—C7'	1.388 (3)	C1'—N1'	1.145 (3)
C6'—C5'	1.391 (3)	C2—N2	1.141 (3)
C6'—C2'	1.431 (4)	C10—C11	1.381 (3)

C8'—O1'—C9'	118.94 (19)	C4'—C5'—C6'	119.1 (2)
C8—O1—C9	118.8 (2)	C4'—C5'—C1'	121.0 (2)
C13'—C12'—C11'	122.1 (2)	C6'—C5'—C1'	119.9 (3)
C13'—C12'—Cl'	119.2 (2)	C3—C4—C5	120.8 (2)
C11'—C12'—Cl'	118.7 (2)	O1'—C8'—C7'	123.6 (2)
C7—C6—C5	120.2 (2)	O1'—C8'—C3'	115.4 (2)
C7—C6—C2	120.3 (2)	C7'—C8'—C3'	120.9 (2)
C5—C6—C2	119.5 (2)	C10'—C9'—C14'	123.2 (2)
C7—C8—O1	124.0 (2)	C10'—C9'—O1'	119.1 (2)
C7—C8—C3	120.7 (2)	C14'—C9'—O1'	117.5 (2)
O1—C8—C3	115.3 (2)	N2'—C2'—C6'	177.9 (3)
C10—C9—C14	122.6 (2)	C8—C7—C6	119.6 (2)
C10—C9—O1	118.2 (2)	C12'—C11'—C10'	118.3 (3)
C14—C9—O1	118.9 (2)	C8'—C7'—C6'	119.1 (2)
C4—C5—C6	118.9 (2)	C5'—C4'—C3'	120.9 (2)
C4—C5—C1	120.0 (2)	C12—C13—C14	121.4 (3)
C6—C5—C1	121.1 (3)	N1—C1—C5	178.4 (3)
C7'—C6'—C5'	120.7 (2)	C13—C12—C11	121.1 (2)
C7'—C6'—C2'	120.0 (2)	C13—C12—Cl	119.2 (2)
C5'—C6'—C2'	119.3 (2)	C11—C12—Cl	119.6 (2)
C4—C3—C8	119.8 (3)	C9'—C10'—C11'	119.6 (2)
C9'—C14'—C13'	116.2 (2)	C4'—C3'—C8'	119.4 (3)
C9'—C14'—C15	123.0 (2)	N1'—C1'—C5'	179.2 (3)
C13'—C14'—C15	120.8 (2)	N2—C2—C6	179.5 (3)
C12'—C13'—C14'	120.6 (2)	C9—C10—C11	119.3 (3)
C9—C14—C13	116.7 (2)	C14'—C15—C14	114.0 (2)
C9—C14—C15	121.9 (2)	C12—C11—C10	119.0 (2)
C13—C14—C15	121.4 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···N1ⁱ	0.97	2.83	3.246 (4)	107

Symmetry code: (i) −x−1, −y+2, −z+1.

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4,4′-[2,2-Methyl­enebis(4-chloro­phenoxy)]­diphthalo­nitrile

Supporting information

Key indicators

checkCIF results

4,4′-[2,2-Methylenebis(4-chlorophenoxy)]diphthalonitrile