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The title compound, C38H24N4O4·2C6H6O, is a 1:2 complex of a pyridyl­ethyl­peryl­ene derivative (EPY) with phenol. The pyridyl­ethyl& groups are attached to the peryl­ene imide skeleton in a trans fashion. The EPY molecule is centrosymmetric. The EPY mol­ecules are stacked along the a axis, with a slip angle of about 32°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805004459/ob6481sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805004459/ob6481Isup2.hkl
Contains datablock I

CCDC reference: 269841

Key indicators

  • Single-crystal X-ray study
  • T = 93 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.039
  • wR factor = 0.098
  • Data-to-parameter ratio = 10.6

checkCIF/PLATON results

No syntax errors found



Alert level A REFLT03_ALERT_3_A Reflection count < 85% complete (theta max?) From the CIF: _diffrn_reflns_theta_max 68.25 From the CIF: _diffrn_reflns_theta_full 0.00 From the CIF: _reflns_number_total 2902 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 3415 Completeness (_total/calc) 84.98%
Author Response: A two-dimentional detector (IP) was used in combination with Cu as radiation.
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.85
Author Response: A two-dimentional detector (IP) was used in combination with Cu as radiation.

Alert level B PLAT022_ALERT_3_B Ratio Unique / Expected Reflections too Low .... 0.85 PLAT355_ALERT_3_B Long O-H Bond (0.82A) O3 - H18 ... 1.08 Ang.
Alert level C GOODF01_ALERT_2_C The least squares goodness of fit parameter lies outside the range 0.80 <> 2.00 Goodness of fit given = 0.782 PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 41 Perc. PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT230_ALERT_2_C Hirshfeld Test Diff for C16 - C17 .. 5.71 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C18 - C19 .. 5.11 su PLAT333_ALERT_2_C Large Average Benzene C-C Dist. C5 -C7_a 1.44 Ang. PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 C6 H6 O
2 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 6 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: TEXSAN (Molecular Structure Corporation, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick 1997); program(s) used to refine structure: TEXSAN; molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: TEXSAN.

(I) top
Crystal data top
C38H24N4O4·2C6H6OZ = 1
Mr = 788.83F(000) = 412.0
Triclinic, P1Dx = 1.407 Mg m3
Hall symbol: -P 1Cu Kα radiation, λ = 1.5418 Å
a = 6.513 (2) ÅCell parameters from 5227 reflections
b = 12.182 (2) Åθ = 3.7–68.2°
c = 12.200 (2) ŵ = 0.76 mm1
α = 89.36 (1)°T = 93 K
β = 81.11 (1)°Platelet, black
γ = 76.81 (2)°0.40 × 0.10 × 0.10 mm
V = 930.8 (4) Å3
Data collection top
Rigaku R-AXIS RAPID Imaging Plate
diffractometer
1186 reflections with F2 > 2σ(F2)
Detector resolution: 10.00 pixels mm-1Rint = 0.057
48 frames, delta ω = 15 deg scansθmax = 68.3°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 56
Tmin = 0.797, Tmax = 0.931k = 1414
7498 measured reflectionsl = 1413
2902 independent reflections
Refinement top
Refinement on F2H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.039 w = 1/[σ2(Fo2) + {0.0[Max(Fo2,0) + 2Fc2]/3}2]
wR(F2) = 0.098(Δ/σ)max = 0.001
S = 0.78Δρmax = 0.39 e Å3
2902 reflectionsΔρmin = 0.40 e Å3
274 parameters
Special details top

Refinement. Refinement using reflections with F2 > -10.0 σ(F2). The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O11.3083 (4)0.5814 (2)0.2140 (2)0.0320 (8)
O21.0842 (4)0.8280 (2)0.5089 (2)0.0331 (9)
O32.1652 (4)1.1360 (2)0.1951 (2)0.0335 (9)
N11.2008 (5)0.7021 (2)0.3641 (2)0.0234 (9)
N21.8245 (5)1.0401 (3)0.2084 (3)0.033 (1)
C11.0558 (6)0.7482 (3)0.4582 (3)0.025 (1)
C20.8734 (6)0.6954 (3)0.4919 (3)0.024 (1)
C30.7278 (6)0.7376 (3)0.5839 (3)0.026 (1)
C40.5549 (6)0.6882 (3)0.6175 (3)0.028 (1)
C50.5266 (6)0.5954 (3)0.5615 (3)0.021 (1)
C60.6747 (6)0.5509 (3)0.4652 (3)0.022 (1)
C70.6537 (6)0.4578 (3)0.4017 (3)0.021 (1)
C80.8007 (6)0.4216 (3)0.3079 (3)0.026 (1)
C90.9714 (6)0.4725 (3)0.2740 (3)0.027 (1)
C100.9953 (6)0.5612 (3)0.3343 (3)0.021 (1)
C111.1799 (6)0.6132 (3)0.2971 (3)0.024 (1)
C120.8502 (6)0.6030 (3)0.4305 (3)0.021 (1)
C131.3844 (6)0.7541 (3)0.3303 (3)0.027 (1)
C141.3195 (6)0.8609 (3)0.2654 (3)0.029 (1)
C151.4990 (6)0.9209 (3)0.2449 (3)0.025 (1)
C161.6004 (6)0.9341 (3)0.1395 (3)0.030 (1)
C171.7578 (7)0.9944 (3)0.1251 (3)0.035 (1)
C181.7294 (7)1.0246 (3)0.3118 (3)0.036 (1)
C191.5690 (6)0.9667 (3)0.3328 (3)0.031 (1)
C202.1852 (6)1.2143 (3)0.1159 (3)0.028 (1)
C212.0277 (6)1.2572 (3)0.0532 (3)0.029 (1)
C222.0580 (7)1.3372 (3)0.0259 (3)0.035 (1)
C232.2489 (7)1.3743 (3)0.0434 (3)0.032 (1)
C242.4051 (6)1.3308 (3)0.0201 (3)0.032 (1)
C252.3753 (6)1.2510 (3)0.0999 (3)0.029 (1)
H10.74430.80020.62460.0310*
H20.45390.71900.68060.0333*
H30.78570.36010.26500.0311*
H41.07050.44540.20920.0330*
H51.43600.77260.39470.0327*
H61.49420.70170.28480.0327*
H71.28580.84130.19630.0353*
H81.19790.90940.30690.0353*
H91.56230.90190.07720.0362*
H101.82281.00410.05150.0424*
H111.77481.05490.37280.0438*
H121.50620.95800.40700.0374*
H131.89841.23210.06410.0347*
H141.94871.36700.06860.0419*
H152.27021.42840.09810.0387*
H162.53461.35570.00920.0389*
H172.48381.22170.14320.0350*
H182.019 (6)1.107 (3)0.203 (3)0.0446*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.031 (2)0.036 (2)0.027 (2)0.009 (1)0.004 (1)0.002 (1)
O20.042 (2)0.033 (2)0.027 (2)0.016 (1)0.003 (1)0.004 (1)
O30.034 (2)0.034 (2)0.034 (2)0.014 (1)0.005 (1)0.009 (1)
N10.022 (2)0.027 (2)0.023 (2)0.011 (2)0.002 (1)0.002 (1)
N20.029 (2)0.028 (2)0.043 (2)0.011 (2)0.007 (2)0.005 (2)
C10.023 (3)0.028 (2)0.024 (2)0.008 (2)0.002 (2)0.006 (2)
C20.028 (3)0.023 (2)0.019 (2)0.005 (2)0.004 (2)0.001 (2)
C30.026 (3)0.028 (2)0.026 (2)0.011 (2)0.005 (2)0.002 (2)
C40.031 (3)0.030 (2)0.021 (2)0.005 (2)0.004 (2)0.002 (2)
C50.020 (2)0.024 (2)0.021 (2)0.006 (2)0.003 (2)0.004 (2)
C60.023 (3)0.021 (2)0.021 (2)0.004 (2)0.003 (2)0.003 (2)
C70.024 (3)0.020 (2)0.020 (2)0.004 (2)0.005 (2)0.002 (2)
C80.028 (3)0.025 (2)0.024 (2)0.006 (2)0.003 (2)0.003 (2)
C90.029 (3)0.031 (2)0.019 (2)0.006 (2)0.003 (2)0.003 (2)
C100.021 (2)0.020 (2)0.021 (2)0.004 (2)0.005 (2)0.001 (2)
C110.022 (3)0.023 (2)0.031 (2)0.012 (2)0.008 (2)0.005 (2)
C120.022 (3)0.021 (2)0.020 (2)0.005 (2)0.006 (2)0.003 (2)
C130.020 (3)0.032 (2)0.032 (2)0.013 (2)0.003 (2)0.001 (2)
C140.026 (3)0.032 (2)0.034 (2)0.012 (2)0.008 (2)0.008 (2)
C150.025 (3)0.021 (2)0.027 (2)0.001 (2)0.004 (2)0.002 (2)
C160.033 (3)0.030 (2)0.031 (2)0.017 (2)0.001 (2)0.005 (2)
C170.040 (3)0.034 (3)0.028 (2)0.007 (2)0.003 (2)0.001 (2)
C180.047 (3)0.028 (2)0.037 (3)0.008 (2)0.015 (2)0.000 (2)
C190.036 (3)0.033 (2)0.028 (2)0.016 (2)0.003 (2)0.007 (2)
C200.034 (3)0.026 (2)0.021 (2)0.004 (2)0.000 (2)0.004 (2)
C210.030 (3)0.028 (2)0.027 (2)0.004 (2)0.004 (2)0.003 (2)
C220.038 (3)0.034 (3)0.028 (2)0.000 (2)0.005 (2)0.001 (2)
C230.033 (3)0.031 (3)0.030 (2)0.008 (2)0.001 (2)0.004 (2)
C240.032 (3)0.035 (2)0.030 (2)0.009 (2)0.001 (2)0.003 (2)
C250.030 (3)0.029 (2)0.026 (2)0.004 (2)0.002 (2)0.000 (2)
Geometric parameters (Å, º) top
O1—C111.215 (4)C10—C121.408 (4)
O2—C11.223 (4)C13—C141.526 (5)
O3—C201.364 (4)C13—H50.950
O3—H181.08 (4)C13—H60.950
N1—C11.401 (4)C14—C151.503 (5)
N1—C111.408 (4)C14—H70.950
N1—C131.479 (4)C14—H80.950
N2—C171.338 (4)C15—C161.377 (5)
N2—C181.348 (5)C15—C191.395 (5)
C1—C21.479 (5)C16—C171.381 (5)
C2—C31.373 (4)C16—H90.950
C2—C121.407 (4)C17—H100.950
C3—C41.399 (5)C18—C191.380 (5)
C3—H10.950C18—H110.950
C4—C51.389 (5)C19—H120.950
C4—H20.950C20—C211.378 (5)
C5—C61.425 (4)C20—C251.395 (5)
C5—C7i1.476 (5)C21—C221.388 (5)
C6—C71.425 (4)C21—H130.950
C6—C121.437 (5)C22—C231.403 (5)
C7—C81.379 (4)C22—H140.950
C8—C91.400 (5)C23—C241.380 (5)
C8—H30.950C23—H150.950
C9—C101.365 (5)C24—C251.392 (5)
C9—H40.950C24—H160.950
C10—C111.491 (5)C25—H170.950
O3···N22.717 (4)C18···H182.53 (4)
C17···H182.70 (4)
C20—O3—H18114 (1)N1—C13—H6109.1
C1—N1—C11124.8 (3)C14—C13—H5109.1
C1—N1—C13117.4 (3)C14—C13—H6109.1
C11—N1—C13117.8 (3)H5—C13—H6109.5
C17—N2—C18116.5 (4)C13—C14—C15110.3 (3)
O2—C1—N1119.9 (4)C13—C14—H7109.2
O2—C1—C2123.0 (4)C13—C14—H8109.3
N1—C1—C2117.1 (3)C15—C14—H7109.3
C1—C2—C3119.1 (4)C15—C14—H8109.3
C1—C2—C12120.3 (4)H7—C14—H8109.5
C3—C2—C12120.7 (4)C14—C15—C16121.9 (4)
C2—C3—C4119.9 (4)C14—C15—C19121.0 (3)
C2—C3—H1120.1C16—C15—C19117.1 (4)
C4—C3—H1120.1C15—C16—C17119.5 (4)
C3—C4—C5122.0 (4)C15—C16—H9120.3
C3—C4—H2119.0C17—C16—H9120.2
C5—C4—H2119.0N2—C17—C16124.1 (4)
C4—C5—C6119.1 (4)N2—C17—H10118.0
C4—C5—C7i121.9 (4)C16—C17—H10118.0
C6—C5—C7i119.0 (3)N2—C18—C19122.9 (4)
C5—C6—C7122.5 (3)N2—C18—H11118.5
C5—C6—C12118.5 (3)C19—C18—H11118.6
C7—C6—C12119.0 (3)C15—C19—C18120.0 (4)
C5i—C7—C6118.5 (3)C15—C19—H12120.0
C5i—C7—C8122.6 (4)C18—C19—H12120.0
C6—C7—C8118.9 (4)O3—C20—C21122.9 (4)
C7—C8—C9122.0 (4)O3—C20—C25117.0 (4)
C7—C8—H3119.0C21—C20—C25120.1 (4)
C9—C8—H3119.0C20—C21—C22120.0 (4)
C8—C9—C10119.9 (4)C20—C21—H13120.0
C8—C9—H4120.1C22—C21—H13120.0
C10—C9—H4120.0C21—C22—C23120.5 (4)
C9—C10—C11118.8 (4)C21—C22—H14119.7
C9—C10—C12121.1 (4)C23—C22—H14119.7
C11—C10—C12120.1 (3)C22—C23—C24118.9 (4)
O1—C11—N1120.6 (4)C22—C23—H15120.5
O1—C11—C10122.9 (4)C24—C23—H15120.6
N1—C11—C10116.5 (3)C23—C24—C25120.9 (4)
C2—C12—C6119.9 (4)C23—C24—H16119.6
C2—C12—C10121.0 (4)C25—C24—H16119.6
C6—C12—C10119.1 (3)C20—C25—C24119.6 (4)
N1—C13—C14111.0 (3)C20—C25—H17120.2
N1—C13—H5109.1C24—C25—H17120.2
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H18···N21.08 (4)1.65 (4)2.717 (4)170 (3)
 

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