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The title compound, C38H24N4O4·2C7H8O, is a 1:2 complex of a pyridylethyl­perylene derivative, EPY, with m-cresol. The EPY mol­ecule has a centre of symmetry and the pyrid­yl­ethyl groups are attached to the perylene-imide skeleton in a trans fashion. The EPY mol­ecules are stacked along the a axis with a slip angle of about 47°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805004447/ob6476sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805004447/ob6476Isup2.hkl
Contains datablock I

CCDC reference: 269837

Key indicators

  • Single-crystal X-ray study
  • T = 93 K
  • Mean [sigma](C-C) = 0.008 Å
  • R factor = 0.100
  • wR factor = 0.118
  • Data-to-parameter ratio = 12.0

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.93
Author Response: A two-dimentional detector (IP) was used in combinaiton with Cu as radiation.

Alert level B DIFMN02_ALERT_2_B The minimum difference density is < -0.1*ZMAX*1.00 _refine_diff_density_min given = -0.900 Test value = -0.800 DIFMX01_ALERT_2_B The maximum difference density is > 0.1*ZMAX*1.00 _refine_diff_density_max given = 1.080 Test value = 0.800 PLAT097_ALERT_2_B Maximum (Positive) Residual Density ............ 1.08 e/A   3 PLAT098_ALERT_2_B Minimum (Negative) Residual Density ............ -0.90 e/A   3
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.618 0.930 Tmin' and Tmax expected: 0.739 0.930 RR' = 0.836 Please check that your absorption correction is appropriate. DIFMN03_ALERT_1_C The minimum difference density is < -0.1*ZMAX*0.75 The relevant atom site should be identified. DIFMX02_ALERT_1_C The minimum difference density is > 0.1*ZMAX*0.75 The relevant atom site should be identified. RADNW01_ALERT_1_C The radiation wavelength lies outside the expected range for the supplied radiation type. Expected range 1.54175-1.54180 Wavelength given = 1.54190 REFLT03_ALERT_3_C Reflection count < 95% complete From the CIF: _diffrn_reflns_theta_max 68.20 From the CIF: _diffrn_reflns_theta_full 68.20 From the CIF: _reflns_number_total 3363 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 3613 Completeness (_total/calc) 93.08% RFACG01_ALERT_3_C The value of the R factor is > 0.10 R factor given 0.100 RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.147 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.15 PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.93 PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 40 Perc. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.83 PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT333_ALERT_2_C Large Average Benzene C-C Dist. C10 -C12_a 1.45 Ang. PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 8 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 C7 H8 O
1 ALERT level A = In general: serious problem 4 ALERT level B = Potentially serious problem 15 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 4 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 10 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: SYSTEM90 (Hou et al., 1994); 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
C38H24N4O4·2C7H8OF(000) = 856.0
Mr = 816.88Dx = 1.367 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.5419 Å
Hall symbol: -P 2ybcCell parameters from 4038 reflections
a = 4.903 (6) Åθ = 3.0–65.6°
b = 29.26 (4) ŵ = 0.73 mm1
c = 13.96 (2) ÅT = 93 K
β = 97.65 (6)°Needle, red
V = 1985 (4) Å30.40 × 0.10 × 0.10 mm
Z = 2
Data collection top
Rigaku R-AXIS RAPID imaging plate
diffractometer
1335 reflections with F2 > 2σ(F2)
Detector resolution: 10.00 pixels mm-1Rint = 0.147
24 frames, δ ω = 30° scansθmax = 68.2°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 05
Tmin = 0.618, Tmax = 0.930k = 035
3443 measured reflectionsl = 1616
3363 independent reflections
Refinement top
Refinement on F2H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.100 w = 1/[σ2(Fo2) + {0.025[Max(Fo2,0) + 2Fc2]/3}2]
wR(F2) = 0.118(Δ/σ)max = 0.0002
S = 1.00Δρmax = 1.08 e Å3
3363 reflectionsΔρmin = 0.90 e Å3
280 parameters
Special details top

Refinement. Refinement using reflections with F2 > -3.0 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
O10.2431 (7)0.6434 (1)0.7752 (3)0.036 (1)
O20.5191 (7)0.4996 (1)0.6876 (3)0.036 (1)
O31.5941 (7)0.6440 (1)0.1952 (2)0.037 (1)
N11.1697 (9)0.6368 (2)0.3457 (3)0.033 (2)
N20.3847 (9)0.5714 (1)0.7349 (3)0.024 (2)
C10.992 (1)0.6661 (2)0.3919 (4)0.037 (2)
C20.777 (1)0.6536 (2)0.4621 (4)0.033 (2)
C30.730 (1)0.6081 (2)0.4846 (4)0.027 (2)
C40.501 (1)0.5930 (2)0.5611 (4)0.038 (2)
C50.607 (1)0.5898 (2)0.6613 (4)0.032 (2)
C60.205 (1)0.6024 (2)0.7880 (4)0.032 (2)
C70.019 (1)0.5836 (2)0.8572 (4)0.023 (2)
C80.199 (1)0.6124 (2)0.9109 (4)0.024 (2)
C90.4173 (10)0.5956 (2)0.9777 (4)0.021 (2)
C100.459 (1)0.5491 (2)0.9903 (4)0.023 (2)
C110.275 (1)0.5185 (2)0.9328 (4)0.020 (2)
C120.312 (1)0.4701 (2)0.9415 (4)0.022 (2)
C130.128 (1)0.4422 (2)0.8824 (4)0.022 (2)
C140.090 (1)0.4598 (2)0.8189 (4)0.027 (2)
C150.127 (1)0.5067 (2)0.8100 (4)0.025 (2)
C160.355 (1)0.5235 (2)0.7405 (4)0.032 (2)
C170.914 (1)0.5772 (2)0.4345 (4)0.028 (2)
C181.128 (1)0.5928 (2)0.3672 (4)0.032 (2)
C190.054 (1)0.5360 (2)0.8662 (4)0.023 (2)
C201.721 (1)0.6858 (2)0.1791 (4)0.025 (2)
C211.944 (1)0.6882 (2)0.1046 (4)0.025 (2)
C222.082 (1)0.7288 (2)0.0829 (4)0.026 (2)
C232.002 (1)0.7670 (2)0.1378 (4)0.035 (2)
C241.778 (1)0.7645 (2)0.2119 (4)0.038 (2)
C251.637 (1)0.7241 (2)0.2320 (4)0.041 (2)
C262.321 (1)0.7306 (2)0.0014 (4)0.041 (2)
H11.43750.64870.24750.0395*
H21.01410.69750.37620.0449*
H30.66230.67650.49490.0396*
H40.43660.56400.54400.0453*
H50.35600.61470.56450.0453*
H60.76160.57000.65640.0384*
H70.65850.61940.68040.0384*
H80.17540.64440.90350.0281*
H90.53840.61651.01410.0260*
H100.15220.41000.88580.0267*
H110.21420.43960.78180.0314*
H120.89420.54540.44720.0335*
H131.24940.57080.33450.0379*
H142.00190.66140.06920.0301*
H152.09740.79500.12510.0419*
H161.72290.79110.24860.0449*
H171.48420.72280.28150.0498*
H182.35220.76140.01820.0485*
H192.27510.71310.05170.0485*
H202.47990.71840.02320.0485*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.042 (3)0.030 (3)0.034 (3)0.006 (2)0.004 (2)0.003 (2)
O20.030 (3)0.035 (3)0.038 (3)0.000 (2)0.006 (2)0.003 (2)
O30.045 (3)0.034 (3)0.028 (3)0.007 (2)0.013 (2)0.003 (2)
N10.033 (4)0.039 (3)0.025 (3)0.010 (3)0.002 (3)0.002 (3)
N20.020 (3)0.026 (3)0.025 (3)0.007 (3)0.001 (2)0.002 (3)
C10.049 (5)0.020 (4)0.043 (4)0.004 (3)0.010 (4)0.003 (3)
C20.036 (4)0.026 (4)0.036 (4)0.003 (3)0.000 (3)0.005 (3)
C30.019 (4)0.042 (4)0.020 (4)0.004 (3)0.005 (3)0.007 (3)
C40.034 (4)0.051 (4)0.028 (4)0.001 (3)0.006 (3)0.008 (3)
C50.029 (4)0.037 (4)0.031 (4)0.004 (3)0.007 (3)0.007 (3)
C60.036 (5)0.023 (4)0.037 (5)0.008 (3)0.009 (4)0.009 (3)
C70.028 (4)0.017 (4)0.025 (4)0.005 (3)0.004 (3)0.006 (3)
C80.022 (4)0.020 (4)0.029 (4)0.007 (3)0.006 (3)0.003 (3)
C90.016 (4)0.023 (4)0.025 (4)0.006 (3)0.004 (3)0.002 (3)
C100.022 (4)0.026 (4)0.022 (4)0.003 (3)0.007 (3)0.007 (3)
C110.016 (4)0.026 (4)0.019 (4)0.003 (3)0.010 (3)0.000 (3)
C120.020 (4)0.024 (4)0.023 (4)0.003 (3)0.004 (3)0.003 (3)
C130.028 (4)0.017 (3)0.023 (4)0.001 (3)0.005 (3)0.000 (3)
C140.023 (4)0.034 (4)0.022 (4)0.005 (3)0.004 (3)0.003 (3)
C150.030 (4)0.032 (4)0.013 (3)0.004 (3)0.001 (3)0.004 (3)
C160.034 (5)0.037 (4)0.028 (4)0.006 (4)0.017 (3)0.002 (4)
C170.028 (4)0.028 (4)0.028 (4)0.004 (3)0.005 (3)0.003 (3)
C180.038 (5)0.033 (4)0.028 (4)0.004 (3)0.010 (3)0.003 (3)
C190.022 (4)0.027 (4)0.019 (4)0.001 (3)0.000 (3)0.002 (3)
C200.019 (4)0.031 (4)0.023 (4)0.003 (3)0.003 (3)0.005 (3)
C210.028 (4)0.022 (3)0.024 (4)0.004 (3)0.004 (3)0.007 (3)
C220.029 (4)0.024 (4)0.025 (4)0.005 (3)0.002 (3)0.003 (3)
C230.042 (4)0.027 (4)0.036 (4)0.020 (4)0.002 (3)0.006 (3)
C240.048 (5)0.029 (4)0.035 (4)0.003 (4)0.001 (3)0.009 (3)
C250.057 (5)0.044 (4)0.020 (4)0.003 (4)0.006 (3)0.006 (3)
C260.040 (4)0.039 (4)0.044 (4)0.001 (3)0.005 (3)0.009 (4)
Geometric parameters (Å, º) top
O1—C61.223 (7)C10—C12i1.485 (7)
O2—C161.233 (7)C11—C121.429 (8)
O3—C201.378 (6)C11—C191.425 (7)
O3—H10.996C12—C131.402 (7)
N1—C11.327 (7)C13—C141.393 (7)
N1—C181.333 (7)C13—H100.951
N2—C51.493 (7)C14—C151.387 (8)
N2—C61.405 (7)C14—H110.949
N2—C161.412 (7)C15—C161.465 (8)
C1—C21.390 (8)C15—C191.399 (8)
C1—H20.949C17—C181.387 (7)
C2—C31.382 (8)C17—H120.950
C2—H30.951C18—H130.950
C3—C41.507 (7)C20—C211.404 (7)
C3—C171.399 (7)C20—C251.377 (8)
C4—C51.558 (8)C21—C221.380 (8)
C4—H40.948C21—H140.950
C4—H50.950C22—C231.382 (8)
C5—H60.950C22—C261.523 (7)
C5—H70.951C23—C241.407 (7)
C6—C71.469 (8)C23—H150.950
C7—C81.370 (7)C24—C251.379 (8)
C7—C191.406 (8)C24—H160.950
C8—C91.410 (7)C25—H170.950
C8—H80.949C26—H180.949
C9—C101.384 (7)C26—H190.952
C9—H90.950C26—H200.944
C10—C111.437 (7)
O1···C23ii3.543 (7)C5···C7v3.496 (8)
O2···C18iii3.246 (7)C6···C9v3.434 (8)
O3···N12.761 (5)C6···C8v3.592 (9)
O3···C9iv3.356 (6)C10···C14vii3.420 (8)
O3···C14iii3.401 (6)C10···C13vii3.585 (9)
O3···C183.431 (6)C11···C16vi3.438 (9)
N2···C7v3.595 (8)C11···C12vii3.581 (9)
C1···C25vi3.454 (9)C12···C19vii3.428 (8)
C1···C20vi3.460 (8)C12···C14vi3.597 (9)
C3···C18vi3.589 (9)C14···C18viii3.318 (8)
C4···C18vi3.463 (8)
C20—O3—H1106.6C11—C12—C13117.5 (4)
C1—N1—C18116.4 (4)C12—C13—C14122.7 (5)
C5—N2—C6118.6 (4)C12—C13—H10118.7
C5—N2—C16117.1 (4)C14—C13—H10118.6
C6—N2—C16124.0 (4)C13—C14—C15120.0 (5)
N1—C1—C2124.2 (5)C13—C14—H11120.0
N1—C1—H2117.8C15—C14—H11120.0
C2—C1—H2118.0C14—C15—C16118.0 (5)
C1—C2—C3120.1 (5)C14—C15—C19119.5 (5)
C1—C2—H3120.0C16—C15—C19122.5 (5)
C3—C2—H3119.9O2—C16—N2118.3 (5)
C2—C3—C4121.9 (5)O2—C16—C15125.9 (5)
C2—C3—C17115.6 (5)N2—C16—C15115.8 (5)
C4—C3—C17122.5 (5)C3—C17—C18120.5 (5)
C3—C4—C5110.5 (4)C3—C17—H12119.6
C3—C4—H4109.0C18—C17—H12119.9
C3—C4—H5108.8N1—C18—C17123.3 (5)
C5—C4—H4109.5N1—C18—H13118.5
C5—C4—H5109.4C17—C18—H13118.2
H4—C4—H5109.7C7—C19—C11119.3 (5)
N2—C5—C4110.0 (4)C7—C19—C15119.7 (5)
N2—C5—H6109.5C11—C19—C15121.0 (5)
N2—C5—H7109.4O3—C20—C21117.1 (5)
C4—C5—H6109.3O3—C20—C25122.6 (4)
C4—C5—H7109.3C21—C20—C25120.3 (5)
H6—C5—H7109.4C20—C21—C22121.0 (5)
O1—C6—N2118.9 (5)C20—C21—H14119.6
O1—C6—C7123.4 (5)C22—C21—H14119.4
N2—C6—C7117.7 (5)C21—C22—C23118.7 (5)
C6—C7—C8120.0 (5)C21—C22—C26120.0 (5)
C6—C7—C19120.2 (5)C23—C22—C26121.3 (5)
C8—C7—C19119.7 (5)C22—C23—C24120.1 (5)
C7—C8—C9121.8 (5)C22—C23—H15119.9
C7—C8—H8119.1C24—C23—H15120.0
C9—C8—H8119.1C23—C24—C25120.9 (5)
C8—C9—C10120.7 (4)C23—C24—H16119.4
C8—C9—H9119.7C25—C24—H16119.6
C10—C9—H9119.6C20—C25—C24118.9 (5)
C9—C10—C11118.2 (5)C20—C25—H17120.6
C9—C10—C12i122.6 (5)C24—C25—H17120.5
C11—C10—C12i119.1 (5)C22—C26—H18109.2
C10—C11—C12120.4 (5)C22—C26—H19109.0
C10—C11—C19120.3 (5)C22—C26—H20109.4
C12—C11—C19119.3 (5)H18—C26—H19109.4
C10i—C12—C11120.4 (4)H18—C26—H20110.1
C10i—C12—C13122.1 (5)H19—C26—H20109.8
Symmetry codes: (i) x+1, y+1, z+2; (ii) x+2, y+3/2, z+1/2; (iii) x2, y+1, z+1; (iv) x2, y, z1; (v) x1, y, z; (vi) x+1, y, z; (vii) x, y+1, z+2; (viii) x1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H1···N11.001.802.761 (5)161
 

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