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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804001758/dn6116sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804001758/dn6116Isup2.hkl
Contains datablock I

CCDC reference: 234920

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

Computing details top

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) top
Crystal data top
C28H28N2O2Z = 2
Mr = 424.52F(000) = 452
Triclinic, P1Dx = 1.174 Mg m3
Hall symbol: -P 1Melting point: 412 K
a = 9.268 (9) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.15 (1) ÅCell parameters from 10727 reflections
c = 13.115 (13) Åθ = 2.0–27.6°
α = 93.919 (8)°µ = 0.07 mm1
β = 101.078 (8)°T = 293 K
γ = 95.278 (8)°Prism, green
V = 1201 (2) Å30.50 × 0.36 × 0.27 mm
Data collection top
Stoe IPDS 2
diffractometer
2920 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.059
Graphite monochromatorθmax = 27.8°, θmin = 2.0°
ω scansh = 1212
20244 measured reflectionsk = 1312
5615 independent reflectionsl = 1717
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)] = 0.044H-atom parameters constrained
wR(F2) = 0.120 w = 1/[σ2(Fo2) + (0.0657P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.87(Δ/σ)max < 0.001
5615 reflectionsΔρmax = 0.21 e Å3
292 parametersΔρmin = 0.12 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.022 (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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.37449 (17)0.48474 (15)0.15623 (12)0.0488 (4)
C20.24312 (17)0.42230 (15)0.09327 (11)0.0485 (4)
C30.16225 (18)0.32049 (16)0.12937 (12)0.0537 (4)
H30.07670.27730.08680.064*
C40.20871 (17)0.28305 (15)0.22861 (11)0.0489 (4)
C50.33592 (16)0.34841 (15)0.29231 (11)0.0463 (4)
C60.41920 (17)0.44672 (15)0.25591 (12)0.0501 (4)
H60.50590.48790.29830.060*
N70.53188 (19)0.66831 (17)0.08891 (13)0.0834 (5)
C70.46176 (19)0.58752 (17)0.11873 (13)0.0589 (4)
N80.1486 (2)0.50187 (18)0.08687 (13)0.0849 (5)
O10.14025 (13)0.18296 (11)0.27130 (8)0.0647 (3)
O20.38319 (12)0.30799 (11)0.38988 (8)0.0539 (3)
C80.19106 (19)0.46558 (17)0.00766 (13)0.0595 (4)
C90.00594 (17)0.11372 (16)0.21740 (11)0.0504 (4)
C100.1186 (2)0.17933 (17)0.20045 (12)0.0589 (4)
H100.11080.27030.21830.071*
C110.25558 (19)0.11133 (19)0.15704 (13)0.0623 (5)
C120.2605 (2)0.02300 (19)0.13230 (14)0.0651 (5)
H120.35100.07150.10340.078*
C130.1354 (2)0.08734 (18)0.14926 (13)0.0619 (5)
H130.14330.17820.13090.074*
C140.00345 (17)0.02089 (16)0.19311 (12)0.0525 (4)
C150.1422 (2)0.09005 (18)0.21128 (14)0.0650 (5)
H150.21210.03760.26850.078*
C160.1198 (3)0.2280 (3)0.2446 (3)0.1204 (10)
H16A0.21210.26600.25470.181*
H16B0.04870.28190.19170.181*
H16C0.08440.22420.30880.181*
C170.2128 (3)0.0889 (4)0.1166 (2)0.1372 (12)
H17A0.30090.13310.12930.206*
H17B0.23760.00130.10300.206*
H17C0.14470.13410.05740.206*
C180.3919 (2)0.1823 (3)0.1415 (2)0.0981 (7)
H18A0.46380.13730.08420.147*
H18B0.36710.27190.12650.147*
H18C0.43210.18320.20370.147*
C190.31455 (16)0.35585 (15)0.46904 (11)0.0463 (4)
C200.27000 (19)0.48123 (16)0.47074 (12)0.0571 (4)
H200.28240.53380.41710.069*
C210.2071 (2)0.53068 (17)0.55083 (13)0.0617 (5)
C220.1915 (2)0.44959 (18)0.62950 (13)0.0646 (5)
H220.14970.47990.68450.077*
C230.23694 (19)0.32523 (18)0.62706 (13)0.0618 (5)
H230.22580.27330.68130.074*
C240.29906 (17)0.27329 (16)0.54692 (12)0.0515 (4)
C250.3439 (2)0.13495 (18)0.54331 (15)0.0744 (5)
H250.38460.12030.48030.089*
C260.2108 (4)0.0339 (2)0.5351 (3)0.1514 (13)
H26A0.24140.05390.53310.227*
H26B0.14060.04280.47250.227*
H26C0.16600.04880.59450.227*
C270.4614 (4)0.1144 (4)0.6354 (2)0.1447 (12)
H27A0.48570.02460.63000.217*
H27B0.42540.13100.69850.217*
H27C0.54810.17460.63660.217*
C280.1605 (3)0.6685 (2)0.55236 (17)0.0930 (7)
H28A0.23140.72650.60260.140*
H28B0.06520.66720.57100.140*
H28C0.15520.70000.48450.140*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0515 (9)0.0452 (9)0.0505 (9)0.0019 (7)0.0155 (7)0.0046 (7)
C20.0532 (9)0.0492 (9)0.0444 (8)0.0016 (7)0.0131 (7)0.0076 (7)
C30.0569 (9)0.0536 (10)0.0464 (8)0.0097 (8)0.0063 (7)0.0062 (7)
C40.0561 (9)0.0434 (8)0.0456 (8)0.0062 (7)0.0113 (7)0.0063 (7)
C50.0497 (8)0.0481 (9)0.0402 (8)0.0026 (7)0.0071 (6)0.0055 (7)
C60.0469 (8)0.0505 (9)0.0501 (9)0.0044 (7)0.0084 (7)0.0013 (7)
N70.0861 (11)0.0762 (11)0.0867 (11)0.0211 (9)0.0235 (9)0.0206 (9)
C70.0605 (10)0.0560 (10)0.0591 (10)0.0070 (8)0.0145 (8)0.0078 (8)
N80.0931 (12)0.0960 (13)0.0636 (10)0.0003 (10)0.0074 (9)0.0289 (9)
O10.0729 (7)0.0604 (7)0.0508 (6)0.0240 (6)0.0016 (5)0.0165 (5)
O20.0564 (6)0.0608 (7)0.0439 (6)0.0056 (5)0.0070 (5)0.0096 (5)
C80.0620 (10)0.0620 (11)0.0531 (10)0.0052 (8)0.0111 (8)0.0120 (8)
C90.0565 (9)0.0510 (10)0.0410 (8)0.0111 (8)0.0095 (7)0.0088 (7)
C100.0757 (12)0.0513 (10)0.0507 (9)0.0014 (9)0.0171 (8)0.0092 (8)
C110.0613 (11)0.0713 (12)0.0575 (10)0.0034 (9)0.0169 (8)0.0188 (9)
C120.0575 (11)0.0692 (13)0.0643 (11)0.0136 (9)0.0079 (8)0.0141 (9)
C130.0697 (11)0.0507 (10)0.0602 (10)0.0118 (9)0.0098 (8)0.0028 (8)
C140.0573 (10)0.0536 (10)0.0454 (8)0.0063 (8)0.0119 (7)0.0083 (7)
C150.0647 (11)0.0665 (12)0.0641 (11)0.0032 (9)0.0135 (9)0.0093 (9)
C160.0968 (18)0.0894 (18)0.179 (3)0.0187 (15)0.0175 (17)0.0560 (18)
C170.119 (2)0.210 (3)0.115 (2)0.076 (2)0.0624 (17)0.051 (2)
C180.0772 (14)0.114 (2)0.1101 (18)0.0222 (14)0.0215 (13)0.0327 (15)
C190.0449 (8)0.0497 (9)0.0396 (8)0.0070 (7)0.0034 (6)0.0023 (7)
C200.0745 (11)0.0500 (10)0.0439 (8)0.0022 (8)0.0079 (8)0.0067 (7)
C210.0798 (12)0.0532 (10)0.0488 (9)0.0030 (9)0.0081 (8)0.0003 (8)
C220.0759 (12)0.0664 (12)0.0522 (10)0.0042 (10)0.0175 (8)0.0013 (9)
C230.0706 (11)0.0629 (11)0.0522 (9)0.0049 (9)0.0156 (8)0.0151 (8)
C240.0538 (9)0.0492 (9)0.0483 (8)0.0053 (7)0.0057 (7)0.0096 (7)
C250.1021 (15)0.0595 (12)0.0699 (12)0.0186 (11)0.0271 (11)0.0218 (9)
C260.182 (3)0.0521 (14)0.213 (4)0.0163 (17)0.034 (3)0.0168 (18)
C270.147 (3)0.153 (3)0.136 (3)0.086 (2)0.004 (2)0.021 (2)
C280.144 (2)0.0654 (13)0.0716 (13)0.0261 (14)0.0223 (13)0.0004 (10)
Geometric parameters (Å, º) top
C1—C61.386 (2)C16—H16B0.9600
C1—C21.402 (2)C16—H16C0.9600
C1—C71.433 (2)C17—H17A0.9600
C2—C31.384 (2)C17—H17B0.9600
C2—C81.432 (2)C17—H17C0.9600
C3—C41.381 (2)C18—H18A0.9600
C3—H30.9300C18—H18B0.9600
C4—O11.3579 (19)C18—H18C0.9600
C4—C51.389 (2)C19—C201.374 (3)
C5—C61.373 (2)C19—C241.385 (2)
C5—O21.374 (2)C20—C211.383 (3)
C6—H60.9300C20—H200.9300
N7—C71.136 (2)C21—C221.384 (3)
N8—C81.136 (2)C21—C281.501 (3)
O1—C91.406 (2)C22—C231.367 (3)
O2—C191.400 (2)C22—H220.9300
C9—C101.374 (3)C23—C241.388 (3)
C9—C141.379 (3)C23—H230.9300
C10—C111.386 (3)C24—C251.501 (3)
C10—H100.9300C25—C271.503 (3)
C11—C121.374 (3)C25—C261.512 (4)
C11—C181.498 (3)C25—H250.9800
C12—C131.372 (3)C26—H26A0.9600
C12—H120.9300C26—H26B0.9600
C13—C141.394 (2)C26—H26C0.9600
C13—H130.9300C27—H27A0.9600
C14—C151.508 (3)C27—H27B0.9600
C15—C161.503 (3)C27—H27C0.9600
C15—C171.511 (3)C28—H28A0.9600
C15—H150.9800C28—H28B0.9600
C16—H16A0.9600C28—H28C0.9600
C6—C1—C2119.34 (13)C15—C17—H17B109.5
C6—C1—C7119.97 (14)H17A—C17—H17B109.5
C2—C1—C7120.69 (14)C15—C17—H17C109.5
C3—C2—C1120.04 (14)H17A—C17—H17C109.5
C3—C2—C8119.94 (14)H17B—C17—H17C109.5
C1—C2—C8120.01 (13)C11—C18—H18A109.5
C4—C3—C2119.94 (14)C11—C18—H18B109.5
C4—C3—H3120.0H18A—C18—H18B109.5
C2—C3—H3120.0C11—C18—H18C109.5
O1—C4—C3125.06 (14)H18A—C18—H18C109.5
O1—C4—C5115.02 (14)H18B—C18—H18C109.5
C3—C4—C5119.92 (13)C20—C19—C24121.91 (15)
C6—C5—O2120.02 (13)C20—C19—O2121.01 (13)
C6—C5—C4120.46 (14)C24—C19—O2117.03 (15)
O2—C5—C4119.38 (13)C19—C20—C21121.19 (15)
C5—C6—C1120.23 (14)C19—C20—H20119.4
C5—C6—H6119.9C21—C20—H20119.4
C1—C6—H6119.9C20—C21—C22117.59 (18)
N7—C7—C1179.4 (2)C20—C21—C28120.63 (16)
C4—O1—C9120.76 (12)C22—C21—C28121.77 (18)
C5—O2—C19116.65 (13)C23—C22—C21120.59 (17)
N8—C8—C2178.7 (2)C23—C22—H22119.7
C10—C9—C14123.08 (15)C21—C22—H22119.7
C10—C9—O1119.09 (16)C22—C23—C24122.73 (15)
C14—C9—O1117.52 (15)C22—C23—H23118.6
C9—C10—C11120.69 (18)C24—C23—H23118.6
C9—C10—H10119.7C19—C24—C23115.99 (17)
C11—C10—H10119.7C19—C24—C25121.78 (16)
C12—C11—C10117.17 (18)C23—C24—C25122.22 (15)
C12—C11—C18122.20 (18)C24—C25—C27112.6 (2)
C10—C11—C18120.6 (2)C24—C25—C26110.5 (2)
C13—C12—C11121.61 (17)C27—C25—C26110.3 (2)
C13—C12—H12119.2C24—C25—H25107.8
C11—C12—H12119.2C27—C25—H25107.8
C12—C13—C14122.14 (18)C26—C25—H25107.8
C12—C13—H13118.9C25—C26—H26A109.5
C14—C13—H13118.9C25—C26—H26B109.5
C9—C14—C13115.31 (17)H26A—C26—H26B109.5
C9—C14—C15121.95 (15)C25—C26—H26C109.5
C13—C14—C15122.73 (18)H26A—C26—H26C109.5
C16—C15—C14113.88 (17)H26B—C26—H26C109.5
C16—C15—C17111.6 (2)C25—C27—H27A109.5
C14—C15—C17110.41 (17)C25—C27—H27B109.5
C16—C15—H15106.9H27A—C27—H27B109.5
C14—C15—H15106.9C25—C27—H27C109.5
C17—C15—H15106.9H27A—C27—H27C109.5
C15—C16—H16A109.5H27B—C27—H27C109.5
C15—C16—H16B109.5C21—C28—H28A109.5
H16A—C16—H16B109.5C21—C28—H28B109.5
C15—C16—H16C109.5H28A—C28—H28B109.5
H16A—C16—H16C109.5C21—C28—H28C109.5
H16B—C16—H16C109.5H28A—C28—H28C109.5
C15—C17—H17A109.5H28B—C28—H28C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6···Cg3i0.932.783.705 (4)171
C17—H17C···Cg2ii0.963.213.818 (5)122
C26—H26C···Cg2iii0.963.314.143 (4)146
C28—H28B···Cg3iv0.963.063.793 (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.
 

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