C—H...π interactions in 4,5-bis(2-iso­propyl-5-methyl­phenoxy)­phthalo­nitrile

The supramolecular structure of the title compound, C₂₈H₂₈N₂O₂, is defined by weak C—H...π interactions. The peripheral aromatic rings lie in approximately orthogonal planes, conferring on the mol­ecule a twisted conformation.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.044
• wR factor = 0.120
• Data-to-parameter ratio = 19.2

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT242_ALERT_2_B Check Low    U(eq) as Compared to Neighbors ....        C15
PLAT242_ALERT_2_B Check Low    U(eq) as Compared to Neighbors ....        C25
PLAT480_ALERT_4_B Long H...A H-Bond Reported H17C   ..  CG2      =       3.21 Ang.
PLAT480_ALERT_4_B Long H...A H-Bond Reported H26C   ..  CG2      =       3.31 Ang.

Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.27 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.78 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C2     -   C8       =       5.10 su
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C1     -   C7       =       1.43 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C2     -   C8       =       1.43 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H28B   ..  CG3      =       3.06 Ang.
PLAT481_ALERT_4_C Long D...A H-Bond Reported C26    ..  CG2      =       4.14 Ang.

   0 ALERT level A = In general: serious problem
   4 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: X-AREA(Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: WinGX (Farrugia, 1999) and PARST (Nardelli, 1995).

(I)

Crystal data

C28H28N2O2	Z = 2
Mr = 424.52	F(000) = 452
Triclinic, P1	Dx = 1.174 Mg m^−3
Hall symbol: -P 1	Melting point: 412 K
a = 9.268 (9) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.15 (1) Å	Cell parameters from 10727 reflections
c = 13.115 (13) Å	θ = 2.0–27.6°
α = 93.919 (8)°	µ = 0.07 mm^−1
β = 101.078 (8)°	T = 293 K
γ = 95.278 (8)°	Prism, green
V = 1201 (2) Å^3	0.50 × 0.36 × 0.27 mm

Data collection

Stoe IPDS 2 diffractometer	2920 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.059
Graphite monochromator	θmax = 27.8°, θmin = 2.0°
ω scans	h = −12→12
20244 measured reflections	k = −13→12
5615 independent reflections	l = −17→17

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.044	H-atom parameters constrained
wR(F^2) = 0.120	w = 1/[σ^2(Fo^2) + (0.0657P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.87	(Δ/σ)max < 0.001
5615 reflections	Δρmax = 0.21 e Å^−3
292 parameters	Δρmin = −0.12 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.022 (3)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.37449 (17)	0.48474 (15)	0.15623 (12)	0.0488 (4)
C2	0.24312 (17)	0.42230 (15)	0.09327 (11)	0.0485 (4)
C3	0.16225 (18)	0.32049 (16)	0.12937 (12)	0.0537 (4)
H3	0.0767	0.2773	0.0868	0.064*
C4	0.20871 (17)	0.28305 (15)	0.22861 (11)	0.0489 (4)
C5	0.33592 (16)	0.34841 (15)	0.29231 (11)	0.0463 (4)
C6	0.41920 (17)	0.44672 (15)	0.25591 (12)	0.0501 (4)
H6	0.5059	0.4879	0.2983	0.060*
N7	0.53188 (19)	0.66831 (17)	0.08891 (13)	0.0834 (5)
C7	0.46176 (19)	0.58752 (17)	0.11873 (13)	0.0589 (4)
N8	0.1486 (2)	0.50187 (18)	−0.08687 (13)	0.0849 (5)
O1	0.14025 (13)	0.18296 (11)	0.27130 (8)	0.0647 (3)
O2	0.38319 (12)	0.30799 (11)	0.38988 (8)	0.0539 (3)
C8	0.19106 (19)	0.46558 (17)	−0.00766 (13)	0.0595 (4)
C9	0.00594 (17)	0.11372 (16)	0.21740 (11)	0.0504 (4)
C10	−0.1186 (2)	0.17933 (17)	0.20045 (12)	0.0589 (4)
H10	−0.1108	0.2703	0.2183	0.071*
C11	−0.25558 (19)	0.11133 (19)	0.15704 (13)	0.0623 (5)
C12	−0.2605 (2)	−0.02300 (19)	0.13230 (14)	0.0651 (5)
H12	−0.3510	−0.0715	0.1034	0.078*
C13	−0.1354 (2)	−0.08734 (18)	0.14926 (13)	0.0619 (5)
H13	−0.1433	−0.1782	0.1309	0.074*
C14	0.00345 (17)	−0.02089 (16)	0.19311 (12)	0.0525 (4)
C15	0.1422 (2)	−0.09005 (18)	0.21128 (14)	0.0650 (5)
H15	0.2121	−0.0376	0.2685	0.078*
C16	0.1198 (3)	−0.2280 (3)	0.2446 (3)	0.1204 (10)
H16A	0.2121	−0.2660	0.2547	0.181*
H16B	0.0487	−0.2819	0.1917	0.181*
H16C	0.0844	−0.2242	0.3088	0.181*
C17	0.2128 (3)	−0.0889 (4)	0.1166 (2)	0.1372 (12)
H17A	0.3009	−0.1331	0.1293	0.206*
H17B	0.2376	0.0013	0.1030	0.206*
H17C	0.1447	−0.1341	0.0574	0.206*
C18	−0.3919 (2)	0.1823 (3)	0.1415 (2)	0.0981 (7)
H18A	−0.4638	0.1373	0.0842	0.147*
H18B	−0.3671	0.2719	0.1265	0.147*
H18C	−0.4321	0.1832	0.2037	0.147*
C19	0.31455 (16)	0.35585 (15)	0.46904 (11)	0.0463 (4)
C20	0.27000 (19)	0.48123 (16)	0.47074 (12)	0.0571 (4)
H20	0.2824	0.5338	0.4171	0.069*
C21	0.2071 (2)	0.53068 (17)	0.55083 (13)	0.0617 (5)
C22	0.1915 (2)	0.44959 (18)	0.62950 (13)	0.0646 (5)
H22	0.1497	0.4799	0.6845	0.077*
C23	0.23694 (19)	0.32523 (18)	0.62706 (13)	0.0618 (5)
H23	0.2258	0.2733	0.6813	0.074*
C24	0.29906 (17)	0.27329 (16)	0.54692 (12)	0.0515 (4)
C25	0.3439 (2)	0.13495 (18)	0.54331 (15)	0.0744 (5)
H25	0.3846	0.1203	0.4803	0.089*
C26	0.2108 (4)	0.0339 (2)	0.5351 (3)	0.1514 (13)
H26A	0.2414	−0.0539	0.5331	0.227*
H26B	0.1406	0.0428	0.4725	0.227*
H26C	0.1660	0.0488	0.5945	0.227*
C27	0.4614 (4)	0.1144 (4)	0.6354 (2)	0.1447 (12)
H27A	0.4857	0.0246	0.6300	0.217*
H27B	0.4254	0.1310	0.6985	0.217*
H27C	0.5481	0.1746	0.6366	0.217*
C28	0.1605 (3)	0.6685 (2)	0.55236 (17)	0.0930 (7)
H28A	0.2314	0.7265	0.6026	0.140*
H28B	0.0652	0.6672	0.5710	0.140*
H28C	0.1552	0.7000	0.4845	0.140*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0515 (9)	0.0452 (9)	0.0505 (9)	−0.0019 (7)	0.0155 (7)	0.0046 (7)
C2	0.0532 (9)	0.0492 (9)	0.0444 (8)	0.0016 (7)	0.0131 (7)	0.0076 (7)
C3	0.0569 (9)	0.0536 (10)	0.0464 (8)	−0.0097 (8)	0.0063 (7)	0.0062 (7)
C4	0.0561 (9)	0.0434 (8)	0.0456 (8)	−0.0062 (7)	0.0113 (7)	0.0063 (7)
C5	0.0497 (8)	0.0481 (9)	0.0402 (8)	0.0026 (7)	0.0071 (6)	0.0055 (7)
C6	0.0469 (8)	0.0505 (9)	0.0501 (9)	−0.0044 (7)	0.0084 (7)	0.0013 (7)
N7	0.0861 (11)	0.0762 (11)	0.0867 (11)	−0.0211 (9)	0.0235 (9)	0.0206 (9)
C7	0.0605 (10)	0.0560 (10)	0.0591 (10)	−0.0070 (8)	0.0145 (8)	0.0078 (8)
N8	0.0931 (12)	0.0960 (13)	0.0636 (10)	0.0003 (10)	0.0074 (9)	0.0289 (9)
O1	0.0729 (7)	0.0604 (7)	0.0508 (6)	−0.0240 (6)	−0.0016 (5)	0.0165 (5)
O2	0.0564 (6)	0.0608 (7)	0.0439 (6)	0.0056 (5)	0.0070 (5)	0.0096 (5)
C8	0.0620 (10)	0.0620 (11)	0.0531 (10)	−0.0052 (8)	0.0111 (8)	0.0120 (8)
C9	0.0565 (9)	0.0510 (10)	0.0410 (8)	−0.0111 (8)	0.0095 (7)	0.0088 (7)
C10	0.0757 (12)	0.0513 (10)	0.0507 (9)	−0.0014 (9)	0.0171 (8)	0.0092 (8)
C11	0.0613 (11)	0.0713 (12)	0.0575 (10)	0.0034 (9)	0.0169 (8)	0.0188 (9)
C12	0.0575 (11)	0.0692 (13)	0.0643 (11)	−0.0136 (9)	0.0079 (8)	0.0141 (9)
C13	0.0697 (11)	0.0507 (10)	0.0602 (10)	−0.0118 (9)	0.0098 (8)	0.0028 (8)
C14	0.0573 (10)	0.0536 (10)	0.0454 (8)	−0.0063 (8)	0.0119 (7)	0.0083 (7)
C15	0.0647 (11)	0.0665 (12)	0.0641 (11)	0.0032 (9)	0.0135 (9)	0.0093 (9)
C16	0.0968 (18)	0.0894 (18)	0.179 (3)	0.0187 (15)	0.0175 (17)	0.0560 (18)
C17	0.119 (2)	0.210 (3)	0.115 (2)	0.076 (2)	0.0624 (17)	0.051 (2)
C18	0.0772 (14)	0.114 (2)	0.1101 (18)	0.0222 (14)	0.0215 (13)	0.0327 (15)
C19	0.0449 (8)	0.0497 (9)	0.0396 (8)	−0.0070 (7)	0.0034 (6)	0.0023 (7)
C20	0.0745 (11)	0.0500 (10)	0.0439 (8)	−0.0022 (8)	0.0079 (8)	0.0067 (7)
C21	0.0798 (12)	0.0532 (10)	0.0488 (9)	0.0030 (9)	0.0081 (8)	−0.0003 (8)
C22	0.0759 (12)	0.0664 (12)	0.0522 (10)	0.0042 (10)	0.0175 (8)	0.0013 (9)
C23	0.0706 (11)	0.0629 (11)	0.0522 (9)	−0.0049 (9)	0.0156 (8)	0.0151 (8)
C24	0.0538 (9)	0.0492 (9)	0.0483 (8)	−0.0053 (7)	0.0057 (7)	0.0096 (7)
C25	0.1021 (15)	0.0595 (12)	0.0699 (12)	0.0186 (11)	0.0271 (11)	0.0218 (9)
C26	0.182 (3)	0.0521 (14)	0.213 (4)	−0.0163 (17)	0.034 (3)	0.0168 (18)
C27	0.147 (3)	0.153 (3)	0.136 (3)	0.086 (2)	−0.004 (2)	0.021 (2)
C28	0.144 (2)	0.0654 (13)	0.0716 (13)	0.0261 (14)	0.0223 (13)	0.0004 (10)

Geometric parameters (Å, º)

C1—C6	1.386 (2)	C16—H16B	0.9600
C1—C2	1.402 (2)	C16—H16C	0.9600
C1—C7	1.433 (2)	C17—H17A	0.9600
C2—C3	1.384 (2)	C17—H17B	0.9600
C2—C8	1.432 (2)	C17—H17C	0.9600
C3—C4	1.381 (2)	C18—H18A	0.9600
C3—H3	0.9300	C18—H18B	0.9600
C4—O1	1.3579 (19)	C18—H18C	0.9600
C4—C5	1.389 (2)	C19—C20	1.374 (3)
C5—C6	1.373 (2)	C19—C24	1.385 (2)
C5—O2	1.374 (2)	C20—C21	1.383 (3)
C6—H6	0.9300	C20—H20	0.9300
N7—C7	1.136 (2)	C21—C22	1.384 (3)
N8—C8	1.136 (2)	C21—C28	1.501 (3)
O1—C9	1.406 (2)	C22—C23	1.367 (3)
O2—C19	1.400 (2)	C22—H22	0.9300
C9—C10	1.374 (3)	C23—C24	1.388 (3)
C9—C14	1.379 (3)	C23—H23	0.9300
C10—C11	1.386 (3)	C24—C25	1.501 (3)
C10—H10	0.9300	C25—C27	1.503 (3)
C11—C12	1.374 (3)	C25—C26	1.512 (4)
C11—C18	1.498 (3)	C25—H25	0.9800
C12—C13	1.372 (3)	C26—H26A	0.9600
C12—H12	0.9300	C26—H26B	0.9600
C13—C14	1.394 (2)	C26—H26C	0.9600
C13—H13	0.9300	C27—H27A	0.9600
C14—C15	1.508 (3)	C27—H27B	0.9600
C15—C16	1.503 (3)	C27—H27C	0.9600
C15—C17	1.511 (3)	C28—H28A	0.9600
C15—H15	0.9800	C28—H28B	0.9600
C16—H16A	0.9600	C28—H28C	0.9600
C6—C1—C2	119.34 (13)	C15—C17—H17B	109.5
C6—C1—C7	119.97 (14)	H17A—C17—H17B	109.5
C2—C1—C7	120.69 (14)	C15—C17—H17C	109.5
C3—C2—C1	120.04 (14)	H17A—C17—H17C	109.5
C3—C2—C8	119.94 (14)	H17B—C17—H17C	109.5
C1—C2—C8	120.01 (13)	C11—C18—H18A	109.5
C4—C3—C2	119.94 (14)	C11—C18—H18B	109.5
C4—C3—H3	120.0	H18A—C18—H18B	109.5
C2—C3—H3	120.0	C11—C18—H18C	109.5
O1—C4—C3	125.06 (14)	H18A—C18—H18C	109.5
O1—C4—C5	115.02 (14)	H18B—C18—H18C	109.5
C3—C4—C5	119.92 (13)	C20—C19—C24	121.91 (15)
C6—C5—O2	120.02 (13)	C20—C19—O2	121.01 (13)
C6—C5—C4	120.46 (14)	C24—C19—O2	117.03 (15)
O2—C5—C4	119.38 (13)	C19—C20—C21	121.19 (15)
C5—C6—C1	120.23 (14)	C19—C20—H20	119.4
C5—C6—H6	119.9	C21—C20—H20	119.4
C1—C6—H6	119.9	C20—C21—C22	117.59 (18)
N7—C7—C1	179.4 (2)	C20—C21—C28	120.63 (16)
C4—O1—C9	120.76 (12)	C22—C21—C28	121.77 (18)
C5—O2—C19	116.65 (13)	C23—C22—C21	120.59 (17)
N8—C8—C2	178.7 (2)	C23—C22—H22	119.7
C10—C9—C14	123.08 (15)	C21—C22—H22	119.7
C10—C9—O1	119.09 (16)	C22—C23—C24	122.73 (15)
C14—C9—O1	117.52 (15)	C22—C23—H23	118.6
C9—C10—C11	120.69 (18)	C24—C23—H23	118.6
C9—C10—H10	119.7	C19—C24—C23	115.99 (17)
C11—C10—H10	119.7	C19—C24—C25	121.78 (16)
C12—C11—C10	117.17 (18)	C23—C24—C25	122.22 (15)
C12—C11—C18	122.20 (18)	C24—C25—C27	112.6 (2)
C10—C11—C18	120.6 (2)	C24—C25—C26	110.5 (2)
C13—C12—C11	121.61 (17)	C27—C25—C26	110.3 (2)
C13—C12—H12	119.2	C24—C25—H25	107.8
C11—C12—H12	119.2	C27—C25—H25	107.8
C12—C13—C14	122.14 (18)	C26—C25—H25	107.8
C12—C13—H13	118.9	C25—C26—H26A	109.5
C14—C13—H13	118.9	C25—C26—H26B	109.5
C9—C14—C13	115.31 (17)	H26A—C26—H26B	109.5
C9—C14—C15	121.95 (15)	C25—C26—H26C	109.5
C13—C14—C15	122.73 (18)	H26A—C26—H26C	109.5
C16—C15—C14	113.88 (17)	H26B—C26—H26C	109.5
C16—C15—C17	111.6 (2)	C25—C27—H27A	109.5
C14—C15—C17	110.41 (17)	C25—C27—H27B	109.5
C16—C15—H15	106.9	H27A—C27—H27B	109.5
C14—C15—H15	106.9	C25—C27—H27C	109.5
C17—C15—H15	106.9	H27A—C27—H27C	109.5
C15—C16—H16A	109.5	H27B—C27—H27C	109.5
C15—C16—H16B	109.5	C21—C28—H28A	109.5
H16A—C16—H16B	109.5	C21—C28—H28B	109.5
C15—C16—H16C	109.5	H28A—C28—H28B	109.5
H16A—C16—H16C	109.5	C21—C28—H28C	109.5
H16B—C16—H16C	109.5	H28A—C28—H28C	109.5
C15—C17—H17A	109.5	H28B—C28—H28C	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···Cg3^i	0.93	2.78	3.705 (4)	171
C17—H17C···Cg2^ii	0.96	3.21	3.818 (5)	122
C26—H26C···Cg2^iii	0.96	3.31	4.143 (4)	146
C28—H28B···Cg3^iv	0.96	3.06	3.793 (5)	134

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