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The title compound, C28H28N2O2, contains three aromatic rings, which are not coplanar and which are distorted from ideal C2v symmetry. The crystal structure involves four intramolecular C—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804002156/wk6008sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804002156/wk6008Isup2.hkl
Contains datablock I

CCDC reference: 236073

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.040
  • wR factor = 0.108
  • Data-to-parameter ratio = 16.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 49 Perc. PLAT230_ALERT_2_C Hirshfeld Test Diff for C2 - C7 = 5.27 su PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C15 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C25 PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C1 - C8 = 1.44 Ang. PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C2 - C7 = 1.43 Ang. PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 19 C3 -C2 -C7 -N1 23.00100.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 20 C1 -C2 -C7 -N1 -157.00100.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 37 C6 -C1 -C8 -N2 -46.00 7.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 38 C2 -C1 -C8 -N2 134.00 7.00 1.555 1.555 1.555 1.555
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 10 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 5 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

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (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); software used to prepare material for publication: WinGX (Farrugia, 1997) and PARST (Nardelli, 1995).

4,5-Bis(2-tert-butylphenoxy)phthalonitrile top
Crystal data top
C28H28N2O2F(000) = 904
Mr = 424.52Dx = 1.135 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 6510 reflections
a = 10.8426 (10) Åθ = 1.9–27.5°
b = 21.704 (2) ŵ = 0.07 mm1
c = 11.0967 (9) ÅT = 293 K
β = 107.920 (7)°Prism, green
V = 2484.6 (4) Å30.50 × 0.35 × 0.22 mm
Z = 4
Data collection top
Stoe IPDS-2
diffractometer
4880 independent reflections
Radiation source: fine-focus sealed tube2371 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.054
Detector resolution: 6.67 pixels mm-1θmax = 26.0°, θmin = 1.9°
ω scansh = 1313
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
k = 2626
Tmin = 0.971, Tmax = 0.985l = 1313
17816 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040H-atom parameters constrained
wR(F2) = 0.108 w = 1/[σ2(Fo2) + (0.0579P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.80(Δ/σ)max = 0.001
4880 reflectionsΔρmax = 0.16 e Å3
290 parametersΔρmin = 0.11 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0113 (11)
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
xyzUiso*/Ueq
O10.26660 (11)0.11817 (5)0.71253 (10)0.0672 (3)
O20.16601 (12)0.15831 (5)0.48530 (10)0.0730 (4)
C20.34345 (15)0.01197 (7)0.53691 (16)0.0598 (4)
C40.28072 (16)0.08069 (7)0.61939 (15)0.0573 (4)
C50.22392 (16)0.10209 (7)0.49563 (15)0.0592 (4)
C30.34077 (16)0.02417 (7)0.63913 (16)0.0622 (4)
H20.37970.01010.72130.075*
C90.34371 (17)0.10909 (7)0.83834 (15)0.0604 (4)
C10.28413 (16)0.00868 (8)0.41399 (16)0.0619 (4)
C70.40662 (18)0.07078 (9)0.55775 (17)0.0693 (5)
C60.22508 (17)0.06607 (8)0.39458 (16)0.0662 (5)
H50.18610.08020.31250.079*
C100.4758 (2)0.11330 (8)0.86352 (19)0.0765 (5)
H100.51100.11930.79780.092*
C240.02039 (17)0.20853 (7)0.30296 (15)0.0606 (4)
C140.28286 (18)0.10118 (7)0.93075 (16)0.0649 (5)
C190.14578 (17)0.19164 (7)0.37233 (15)0.0612 (4)
C80.28348 (18)0.02910 (9)0.30755 (19)0.0760 (5)
C200.2538 (2)0.20896 (9)0.34057 (19)0.0803 (5)
H200.33580.19680.39070.096*
C130.3680 (2)0.09828 (10)1.05402 (19)0.0873 (6)
H130.33390.09371.12080.105*
C150.13659 (19)0.09541 (8)0.90162 (17)0.0736 (5)
C110.5553 (2)0.10858 (10)0.9860 (2)0.0930 (6)
H110.64490.10991.00420.112*
C250.09936 (18)0.18969 (8)0.3387 (2)0.0757 (5)
N10.45679 (18)0.11752 (8)0.57462 (17)0.0933 (5)
C230.0128 (2)0.24470 (8)0.19737 (18)0.0808 (6)
H230.06840.25790.14740.097*
C120.5003 (3)0.10184 (11)1.0807 (2)0.0998 (7)
H120.55320.09961.16430.120*
C220.1187 (3)0.26185 (9)0.1634 (2)0.0967 (7)
H220.10800.28570.09130.116*
C170.0679 (2)0.15388 (10)0.8379 (2)0.0991 (7)
H17A0.02400.14920.82020.149*
H17B0.08730.16070.76020.149*
H17C0.09730.18840.89340.149*
N20.27938 (19)0.05860 (10)0.22195 (19)0.1115 (7)
C210.2400 (3)0.24427 (10)0.2345 (2)0.0962 (7)
H210.31220.25600.21160.115*
C270.0922 (2)0.21610 (11)0.4691 (2)0.1034 (7)
H27A0.01290.20310.53050.155*
H27B0.16450.20140.49360.155*
H27C0.09470.26030.46480.155*
C160.0889 (2)0.03897 (10)0.8169 (2)0.1040 (7)
H16A0.00330.03520.79810.156*
H16B0.13020.00260.86010.156*
H16C0.11000.04380.73950.156*
C180.0970 (2)0.08603 (11)1.0219 (2)0.1050 (7)
H18A0.00440.08260.99940.158*
H18B0.12570.12061.07750.158*
H18C0.13620.04901.06400.158*
C260.1098 (2)0.11925 (9)0.3379 (3)0.1152 (9)
H26A0.02930.10200.38930.173*
H26B0.12870.10440.25270.173*
H26C0.17810.10720.37130.173*
C280.2240 (2)0.21457 (11)0.2442 (2)0.1144 (8)
H28A0.29730.20160.26900.172*
H28B0.23210.19900.16110.172*
H28C0.22090.25880.24300.172*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0843 (8)0.0655 (7)0.0494 (7)0.0149 (6)0.0171 (6)0.0008 (6)
O20.0928 (9)0.0715 (8)0.0567 (7)0.0248 (6)0.0260 (6)0.0109 (6)
C20.0594 (10)0.0565 (10)0.0636 (11)0.0019 (8)0.0191 (8)0.0000 (8)
C40.0654 (10)0.0581 (9)0.0492 (10)0.0032 (8)0.0189 (8)0.0005 (8)
C50.0649 (10)0.0594 (9)0.0541 (11)0.0095 (8)0.0195 (8)0.0050 (8)
C30.0709 (11)0.0592 (10)0.0545 (11)0.0037 (8)0.0161 (9)0.0049 (8)
C90.0724 (12)0.0560 (9)0.0477 (10)0.0051 (8)0.0112 (9)0.0008 (8)
C10.0604 (10)0.0670 (10)0.0597 (11)0.0028 (8)0.0204 (8)0.0060 (9)
C70.0701 (12)0.0638 (11)0.0728 (12)0.0015 (10)0.0203 (9)0.0049 (9)
C60.0708 (11)0.0765 (12)0.0499 (10)0.0114 (9)0.0169 (8)0.0026 (9)
C100.0821 (14)0.0775 (12)0.0687 (13)0.0015 (10)0.0213 (11)0.0033 (10)
C240.0722 (11)0.0478 (9)0.0572 (10)0.0021 (8)0.0131 (9)0.0007 (8)
C140.0837 (13)0.0563 (10)0.0532 (11)0.0035 (8)0.0187 (10)0.0014 (8)
C190.0744 (12)0.0575 (9)0.0509 (10)0.0043 (8)0.0180 (9)0.0062 (8)
C80.0726 (13)0.0858 (13)0.0693 (13)0.0123 (10)0.0212 (10)0.0103 (11)
C200.0756 (13)0.0894 (14)0.0758 (13)0.0023 (10)0.0231 (11)0.0016 (11)
C130.1051 (18)0.0970 (15)0.0569 (13)0.0099 (12)0.0203 (12)0.0042 (10)
C150.0858 (14)0.0726 (11)0.0664 (12)0.0049 (10)0.0295 (10)0.0012 (9)
C110.0813 (14)0.1033 (16)0.0821 (16)0.0028 (11)0.0071 (13)0.0102 (12)
C250.0698 (12)0.0594 (10)0.0973 (14)0.0034 (9)0.0248 (11)0.0027 (10)
N10.0998 (13)0.0708 (11)0.1051 (14)0.0148 (10)0.0250 (10)0.0050 (9)
C230.1029 (16)0.0662 (11)0.0665 (12)0.0136 (11)0.0160 (11)0.0106 (10)
C120.1042 (19)0.1130 (18)0.0635 (14)0.0050 (14)0.0019 (13)0.0012 (12)
C220.140 (2)0.0748 (13)0.0834 (16)0.0031 (14)0.0468 (16)0.0208 (11)
C170.0954 (16)0.1061 (16)0.1018 (17)0.0162 (13)0.0390 (13)0.0171 (13)
N20.1162 (15)0.1271 (16)0.0900 (14)0.0245 (12)0.0299 (11)0.0338 (13)
C210.1115 (19)0.0869 (15)0.1026 (18)0.0179 (13)0.0511 (15)0.0067 (13)
C270.1086 (17)0.1088 (17)0.1101 (18)0.0177 (13)0.0594 (15)0.0032 (14)
C160.1003 (16)0.0989 (16)0.1165 (19)0.0307 (13)0.0388 (14)0.0293 (13)
C180.1239 (19)0.1139 (17)0.0934 (16)0.0102 (14)0.0571 (15)0.0067 (13)
C260.0961 (16)0.0621 (12)0.200 (3)0.0060 (11)0.0644 (17)0.0022 (14)
C280.0777 (15)0.0938 (16)0.153 (2)0.0082 (12)0.0074 (14)0.0105 (15)
Geometric parameters (Å, º) top
O1—C41.3603 (18)C15—C161.534 (3)
O1—C91.4031 (19)C15—C181.536 (3)
O2—C51.3608 (18)C11—C121.366 (3)
O2—C191.4050 (18)C11—H110.9300
C2—C31.387 (2)C25—C281.532 (3)
C2—C11.391 (2)C25—C261.533 (3)
C2—C71.433 (3)C25—C271.536 (3)
C4—C31.374 (2)C23—C221.366 (3)
C4—C51.400 (2)C23—H230.9300
C5—C61.370 (2)C12—H120.9300
C3—H20.9300C22—C211.363 (3)
C9—C101.376 (3)C22—H220.9300
C9—C141.390 (2)C17—H17A0.9600
C1—C61.387 (2)C17—H17B0.9600
C1—C81.436 (3)C17—H17C0.9600
C7—N11.139 (2)C21—H210.9300
C6—H50.9300C27—H27A0.9600
C10—C111.371 (3)C27—H27B0.9600
C10—H100.9300C27—H27C0.9600
C24—C191.390 (2)C16—H16A0.9600
C24—C231.392 (2)C16—H16B0.9600
C24—C251.526 (2)C16—H16C0.9600
C14—C131.397 (3)C18—H18A0.9600
C14—C151.523 (3)C18—H18B0.9600
C19—C201.375 (2)C18—H18C0.9600
C8—N21.135 (2)C26—H26A0.9600
C20—C211.374 (3)C26—H26B0.9600
C20—H200.9300C26—H26C0.9600
C13—C121.375 (3)C28—H28A0.9600
C13—H130.9300C28—H28B0.9600
C15—C171.530 (3)C28—H28C0.9600
C4—O1—C9120.01 (12)C24—C25—C26109.46 (15)
C5—O2—C19118.56 (12)C28—C25—C26107.42 (18)
C3—C2—C1120.01 (15)C24—C25—C27110.17 (16)
C3—C2—C7120.06 (16)C28—C25—C27106.98 (17)
C1—C2—C7119.93 (15)C26—C25—C27111.09 (19)
O1—C4—C3124.83 (15)C22—C23—C24123.3 (2)
O1—C4—C5115.38 (14)C22—C23—H23118.3
C3—C4—C5119.74 (15)C24—C23—H23118.3
O2—C5—C6124.26 (15)C11—C12—C13120.9 (2)
O2—C5—C4115.61 (14)C11—C12—H12119.5
C6—C5—C4120.10 (15)C13—C12—H12119.5
C4—C3—C2120.18 (16)C21—C22—C23120.5 (2)
C4—C3—H2119.9C21—C22—H22119.8
C2—C3—H2119.9C23—C22—H22119.8
C10—C9—C14124.01 (16)C15—C17—H17A109.5
C10—C9—O1117.21 (16)C15—C17—H17B109.5
C14—C9—O1118.59 (16)H17A—C17—H17B109.5
C6—C1—C2119.59 (15)C15—C17—H17C109.5
C6—C1—C8119.99 (16)H17A—C17—H17C109.5
C2—C1—C8120.42 (16)H17B—C17—H17C109.5
N1—C7—C2179.8 (2)C22—C21—C20118.9 (2)
C5—C6—C1120.36 (16)C22—C21—H21120.6
C5—C6—H5119.8C20—C21—H21120.6
C1—C6—H5119.8C25—C27—H27A109.5
C11—C10—C9119.62 (19)C25—C27—H27B109.5
C11—C10—H10120.2H27A—C27—H27B109.5
C9—C10—H10120.2C25—C27—H27C109.5
C19—C24—C23114.15 (17)H27A—C27—H27C109.5
C19—C24—C25123.44 (15)H27B—C27—H27C109.5
C23—C24—C25122.41 (17)C15—C16—H16A109.5
C9—C14—C13114.03 (18)C15—C16—H16B109.5
C9—C14—C15123.58 (16)H16A—C16—H16B109.5
C13—C14—C15122.39 (17)C15—C16—H16C109.5
C20—C19—C24123.44 (16)H16A—C16—H16C109.5
C20—C19—O2117.26 (16)H16B—C16—H16C109.5
C24—C19—O2119.18 (15)C15—C18—H18A109.5
N2—C8—C1178.1 (2)C15—C18—H18B109.5
C21—C20—C19119.7 (2)H18A—C18—H18B109.5
C21—C20—H20120.1C15—C18—H18C109.5
C19—C20—H20120.1H18A—C18—H18C109.5
C12—C13—C14122.7 (2)H18B—C18—H18C109.5
C12—C13—H13118.7C25—C26—H26A109.5
C14—C13—H13118.7C25—C26—H26B109.5
C14—C15—C17110.92 (15)H26A—C26—H26B109.5
C14—C15—C16109.17 (16)C25—C26—H26C109.5
C17—C15—C16110.78 (18)H26A—C26—H26C109.5
C14—C15—C18112.17 (17)H26B—C26—H26C109.5
C17—C15—C18106.55 (17)C25—C28—H28A109.5
C16—C15—C18107.17 (17)C25—C28—H28B109.5
C12—C11—C10118.7 (2)H28A—C28—H28B109.5
C12—C11—H11120.6C25—C28—H28C109.5
C10—C11—H11120.6H28A—C28—H28C109.5
C24—C25—C28111.67 (17)H28B—C28—H28C109.5
C9—O1—C4—C317.6 (2)C25—C24—C19—C20179.55 (16)
C9—O1—C4—C5165.01 (15)C23—C24—C19—O2176.09 (14)
C19—O2—C5—C623.2 (2)C25—C24—C19—O23.6 (2)
C19—O2—C5—C4159.14 (15)C5—O2—C19—C2062.6 (2)
O1—C4—C5—O22.1 (2)C5—O2—C19—C24121.21 (16)
C3—C4—C5—O2179.59 (15)C6—C1—C8—N246 (7)
O1—C4—C5—C6175.73 (15)C2—C1—C8—N2134 (7)
C3—C4—C5—C61.8 (2)C24—C19—C20—C210.7 (3)
O1—C4—C3—C2176.31 (15)O2—C19—C20—C21176.74 (17)
C5—C4—C3—C21.0 (2)C9—C14—C13—C121.1 (3)
C1—C2—C3—C40.6 (2)C15—C14—C13—C12178.25 (19)
C7—C2—C3—C4179.73 (16)C9—C14—C15—C1761.9 (2)
C4—O1—C9—C1059.7 (2)C13—C14—C15—C17118.79 (19)
C4—O1—C9—C14125.09 (16)C9—C14—C15—C1660.4 (2)
C3—C2—C1—C61.4 (2)C13—C14—C15—C16118.9 (2)
C7—C2—C1—C6178.93 (16)C9—C14—C15—C18179.08 (16)
C3—C2—C1—C8178.39 (16)C13—C14—C15—C180.2 (2)
C7—C2—C1—C81.2 (2)C9—C10—C11—C122.2 (3)
C3—C2—C7—N123 (100)C19—C24—C25—C28179.51 (16)
C1—C2—C7—N1157 (100)C23—C24—C25—C280.8 (2)
O2—C5—C6—C1178.58 (15)C19—C24—C25—C2660.7 (2)
C4—C5—C6—C11.0 (3)C23—C24—C25—C26119.7 (2)
C2—C1—C6—C50.6 (3)C19—C24—C25—C2761.8 (2)
C8—C1—C6—C5179.22 (16)C23—C24—C25—C27117.89 (19)
C14—C9—C10—C111.1 (3)C19—C24—C23—C220.6 (3)
O1—C9—C10—C11176.03 (16)C25—C24—C23—C22179.73 (18)
C10—C9—C14—C130.5 (2)C10—C11—C12—C131.6 (3)
O1—C9—C14—C13174.32 (15)C14—C13—C12—C110.1 (3)
C10—C9—C14—C15178.85 (16)C24—C23—C22—C210.7 (3)
O1—C9—C14—C156.3 (2)C23—C22—C21—C200.1 (3)
C23—C24—C19—C200.1 (2)C19—C20—C21—C220.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C17—H17B···O10.962.353.004 (2)124
C27—H27A···O20.962.363.022 (2)126
C16—H16C···O10.962.433.063 (2)123
C26—H26A···O20.962.393.054 (3)126
 

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