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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
CCDC reference: 269841
Key indicators
- Single-crystal X-ray study
- T = 93 K
- Mean (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
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.
Crystal data top
C38H24N4O4·2C6H6O | Z = 1 |
Mr = 788.83 | F(000) = 412.0 |
Triclinic, P1 | Dx = 1.407 Mg m−3 |
Hall symbol: -P 1 | Cu Kα radiation, λ = 1.5418 Å |
a = 6.513 (2) Å | Cell parameters from 5227 reflections |
b = 12.182 (2) Å | θ = 3.7–68.2° |
c = 12.200 (2) Å | µ = 0.76 mm−1 |
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-1 | Rint = 0.057 |
48 frames, delta ω = 15 deg scans | θmax = 68.3° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −5→6 |
Tmin = 0.797, Tmax = 0.931 | k = −14→14 |
7498 measured reflections | l = −14→13 |
2902 independent reflections | |
Refinement top
Refinement on F2 | H 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 = 0.78 | Δρmax = 0.39 e Å−3 |
2902 reflections | Δρmin = −0.40 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
O1 | 1.3083 (4) | 0.5814 (2) | 0.2140 (2) | 0.0320 (8) | |
O2 | 1.0842 (4) | 0.8280 (2) | 0.5089 (2) | 0.0331 (9) | |
O3 | 2.1652 (4) | 1.1360 (2) | 0.1951 (2) | 0.0335 (9) | |
N1 | 1.2008 (5) | 0.7021 (2) | 0.3641 (2) | 0.0234 (9) | |
N2 | 1.8245 (5) | 1.0401 (3) | 0.2084 (3) | 0.033 (1) | |
C1 | 1.0558 (6) | 0.7482 (3) | 0.4582 (3) | 0.025 (1) | |
C2 | 0.8734 (6) | 0.6954 (3) | 0.4919 (3) | 0.024 (1) | |
C3 | 0.7278 (6) | 0.7376 (3) | 0.5839 (3) | 0.026 (1) | |
C4 | 0.5549 (6) | 0.6882 (3) | 0.6175 (3) | 0.028 (1) | |
C5 | 0.5266 (6) | 0.5954 (3) | 0.5615 (3) | 0.021 (1) | |
C6 | 0.6747 (6) | 0.5509 (3) | 0.4652 (3) | 0.022 (1) | |
C7 | 0.6537 (6) | 0.4578 (3) | 0.4017 (3) | 0.021 (1) | |
C8 | 0.8007 (6) | 0.4216 (3) | 0.3079 (3) | 0.026 (1) | |
C9 | 0.9714 (6) | 0.4725 (3) | 0.2740 (3) | 0.027 (1) | |
C10 | 0.9953 (6) | 0.5612 (3) | 0.3343 (3) | 0.021 (1) | |
C11 | 1.1799 (6) | 0.6132 (3) | 0.2971 (3) | 0.024 (1) | |
C12 | 0.8502 (6) | 0.6030 (3) | 0.4305 (3) | 0.021 (1) | |
C13 | 1.3844 (6) | 0.7541 (3) | 0.3303 (3) | 0.027 (1) | |
C14 | 1.3195 (6) | 0.8609 (3) | 0.2654 (3) | 0.029 (1) | |
C15 | 1.4990 (6) | 0.9209 (3) | 0.2449 (3) | 0.025 (1) | |
C16 | 1.6004 (6) | 0.9341 (3) | 0.1395 (3) | 0.030 (1) | |
C17 | 1.7578 (7) | 0.9944 (3) | 0.1251 (3) | 0.035 (1) | |
C18 | 1.7294 (7) | 1.0246 (3) | 0.3118 (3) | 0.036 (1) | |
C19 | 1.5690 (6) | 0.9667 (3) | 0.3328 (3) | 0.031 (1) | |
C20 | 2.1852 (6) | 1.2143 (3) | 0.1159 (3) | 0.028 (1) | |
C21 | 2.0277 (6) | 1.2572 (3) | 0.0532 (3) | 0.029 (1) | |
C22 | 2.0580 (7) | 1.3372 (3) | −0.0259 (3) | 0.035 (1) | |
C23 | 2.2489 (7) | 1.3743 (3) | −0.0434 (3) | 0.032 (1) | |
C24 | 2.4051 (6) | 1.3308 (3) | 0.0201 (3) | 0.032 (1) | |
C25 | 2.3753 (6) | 1.2510 (3) | 0.0999 (3) | 0.029 (1) | |
H1 | 0.7443 | 0.8002 | 0.6246 | 0.0310* | |
H2 | 0.4539 | 0.7190 | 0.6806 | 0.0333* | |
H3 | 0.7857 | 0.3601 | 0.2650 | 0.0311* | |
H4 | 1.0705 | 0.4454 | 0.2092 | 0.0330* | |
H5 | 1.4360 | 0.7726 | 0.3947 | 0.0327* | |
H6 | 1.4942 | 0.7017 | 0.2848 | 0.0327* | |
H7 | 1.2858 | 0.8413 | 0.1963 | 0.0353* | |
H8 | 1.1979 | 0.9094 | 0.3069 | 0.0353* | |
H9 | 1.5623 | 0.9019 | 0.0772 | 0.0362* | |
H10 | 1.8228 | 1.0041 | 0.0515 | 0.0424* | |
H11 | 1.7748 | 1.0549 | 0.3728 | 0.0438* | |
H12 | 1.5062 | 0.9580 | 0.4070 | 0.0374* | |
H13 | 1.8984 | 1.2321 | 0.0641 | 0.0347* | |
H14 | 1.9487 | 1.3670 | −0.0686 | 0.0419* | |
H15 | 2.2702 | 1.4284 | −0.0981 | 0.0387* | |
H16 | 2.5346 | 1.3557 | 0.0092 | 0.0389* | |
H17 | 2.4838 | 1.2217 | 0.1432 | 0.0350* | |
H18 | 2.019 (6) | 1.107 (3) | 0.203 (3) | 0.0446* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.031 (2) | 0.036 (2) | 0.027 (2) | −0.009 (1) | 0.004 (1) | −0.002 (1) |
O2 | 0.042 (2) | 0.033 (2) | 0.027 (2) | −0.016 (1) | −0.003 (1) | −0.004 (1) |
O3 | 0.034 (2) | 0.034 (2) | 0.034 (2) | −0.014 (1) | −0.005 (1) | 0.009 (1) |
N1 | 0.022 (2) | 0.027 (2) | 0.023 (2) | −0.011 (2) | −0.002 (1) | 0.002 (1) |
N2 | 0.029 (2) | 0.028 (2) | 0.043 (2) | −0.011 (2) | −0.007 (2) | 0.005 (2) |
C1 | 0.023 (3) | 0.028 (2) | 0.024 (2) | −0.008 (2) | −0.002 (2) | 0.006 (2) |
C2 | 0.028 (3) | 0.023 (2) | 0.019 (2) | −0.005 (2) | −0.004 (2) | 0.001 (2) |
C3 | 0.026 (3) | 0.028 (2) | 0.026 (2) | −0.011 (2) | −0.005 (2) | −0.002 (2) |
C4 | 0.031 (3) | 0.030 (2) | 0.021 (2) | −0.005 (2) | −0.004 (2) | −0.002 (2) |
C5 | 0.020 (2) | 0.024 (2) | 0.021 (2) | −0.006 (2) | −0.003 (2) | 0.004 (2) |
C6 | 0.023 (3) | 0.021 (2) | 0.021 (2) | −0.004 (2) | −0.003 (2) | 0.003 (2) |
C7 | 0.024 (3) | 0.020 (2) | 0.020 (2) | −0.004 (2) | −0.005 (2) | 0.002 (2) |
C8 | 0.028 (3) | 0.025 (2) | 0.024 (2) | −0.006 (2) | −0.003 (2) | −0.003 (2) |
C9 | 0.029 (3) | 0.031 (2) | 0.019 (2) | −0.006 (2) | 0.003 (2) | 0.003 (2) |
C10 | 0.021 (2) | 0.020 (2) | 0.021 (2) | −0.004 (2) | −0.005 (2) | −0.001 (2) |
C11 | 0.022 (3) | 0.023 (2) | 0.031 (2) | −0.012 (2) | −0.008 (2) | 0.005 (2) |
C12 | 0.022 (3) | 0.021 (2) | 0.020 (2) | −0.005 (2) | −0.006 (2) | 0.003 (2) |
C13 | 0.020 (3) | 0.032 (2) | 0.032 (2) | −0.013 (2) | −0.003 (2) | 0.001 (2) |
C14 | 0.026 (3) | 0.032 (2) | 0.034 (2) | −0.012 (2) | −0.008 (2) | 0.008 (2) |
C15 | 0.025 (3) | 0.021 (2) | 0.027 (2) | −0.001 (2) | −0.004 (2) | 0.002 (2) |
C16 | 0.033 (3) | 0.030 (2) | 0.031 (2) | −0.017 (2) | −0.001 (2) | −0.005 (2) |
C17 | 0.040 (3) | 0.034 (3) | 0.028 (2) | −0.007 (2) | 0.003 (2) | 0.001 (2) |
C18 | 0.047 (3) | 0.028 (2) | 0.037 (3) | −0.008 (2) | −0.015 (2) | −0.000 (2) |
C19 | 0.036 (3) | 0.033 (2) | 0.028 (2) | −0.016 (2) | −0.003 (2) | 0.007 (2) |
C20 | 0.034 (3) | 0.026 (2) | 0.021 (2) | −0.004 (2) | 0.000 (2) | −0.004 (2) |
C21 | 0.030 (3) | 0.028 (2) | 0.027 (2) | −0.004 (2) | −0.004 (2) | −0.003 (2) |
C22 | 0.038 (3) | 0.034 (3) | 0.028 (2) | −0.000 (2) | −0.005 (2) | −0.001 (2) |
C23 | 0.033 (3) | 0.031 (3) | 0.030 (2) | −0.008 (2) | 0.001 (2) | 0.004 (2) |
C24 | 0.032 (3) | 0.035 (2) | 0.030 (2) | −0.009 (2) | 0.001 (2) | −0.003 (2) |
C25 | 0.030 (3) | 0.029 (2) | 0.026 (2) | −0.004 (2) | −0.002 (2) | 0.000 (2) |
Geometric parameters (Å, º) top
O1—C11 | 1.215 (4) | C10—C12 | 1.408 (4) |
O2—C1 | 1.223 (4) | C13—C14 | 1.526 (5) |
O3—C20 | 1.364 (4) | C13—H5 | 0.950 |
O3—H18 | 1.08 (4) | C13—H6 | 0.950 |
N1—C1 | 1.401 (4) | C14—C15 | 1.503 (5) |
N1—C11 | 1.408 (4) | C14—H7 | 0.950 |
N1—C13 | 1.479 (4) | C14—H8 | 0.950 |
N2—C17 | 1.338 (4) | C15—C16 | 1.377 (5) |
N2—C18 | 1.348 (5) | C15—C19 | 1.395 (5) |
C1—C2 | 1.479 (5) | C16—C17 | 1.381 (5) |
C2—C3 | 1.373 (4) | C16—H9 | 0.950 |
C2—C12 | 1.407 (4) | C17—H10 | 0.950 |
C3—C4 | 1.399 (5) | C18—C19 | 1.380 (5) |
C3—H1 | 0.950 | C18—H11 | 0.950 |
C4—C5 | 1.389 (5) | C19—H12 | 0.950 |
C4—H2 | 0.950 | C20—C21 | 1.378 (5) |
C5—C6 | 1.425 (4) | C20—C25 | 1.395 (5) |
C5—C7i | 1.476 (5) | C21—C22 | 1.388 (5) |
C6—C7 | 1.425 (4) | C21—H13 | 0.950 |
C6—C12 | 1.437 (5) | C22—C23 | 1.403 (5) |
C7—C8 | 1.379 (4) | C22—H14 | 0.950 |
C8—C9 | 1.400 (5) | C23—C24 | 1.380 (5) |
C8—H3 | 0.950 | C23—H15 | 0.950 |
C9—C10 | 1.365 (5) | C24—C25 | 1.392 (5) |
C9—H4 | 0.950 | C24—H16 | 0.950 |
C10—C11 | 1.491 (5) | C25—H17 | 0.950 |
| | | |
O3···N2 | 2.717 (4) | C18···H18 | 2.53 (4) |
C17···H18 | 2.70 (4) | | |
| | | |
C20—O3—H18 | 114 (1) | N1—C13—H6 | 109.1 |
C1—N1—C11 | 124.8 (3) | C14—C13—H5 | 109.1 |
C1—N1—C13 | 117.4 (3) | C14—C13—H6 | 109.1 |
C11—N1—C13 | 117.8 (3) | H5—C13—H6 | 109.5 |
C17—N2—C18 | 116.5 (4) | C13—C14—C15 | 110.3 (3) |
O2—C1—N1 | 119.9 (4) | C13—C14—H7 | 109.2 |
O2—C1—C2 | 123.0 (4) | C13—C14—H8 | 109.3 |
N1—C1—C2 | 117.1 (3) | C15—C14—H7 | 109.3 |
C1—C2—C3 | 119.1 (4) | C15—C14—H8 | 109.3 |
C1—C2—C12 | 120.3 (4) | H7—C14—H8 | 109.5 |
C3—C2—C12 | 120.7 (4) | C14—C15—C16 | 121.9 (4) |
C2—C3—C4 | 119.9 (4) | C14—C15—C19 | 121.0 (3) |
C2—C3—H1 | 120.1 | C16—C15—C19 | 117.1 (4) |
C4—C3—H1 | 120.1 | C15—C16—C17 | 119.5 (4) |
C3—C4—C5 | 122.0 (4) | C15—C16—H9 | 120.3 |
C3—C4—H2 | 119.0 | C17—C16—H9 | 120.2 |
C5—C4—H2 | 119.0 | N2—C17—C16 | 124.1 (4) |
C4—C5—C6 | 119.1 (4) | N2—C17—H10 | 118.0 |
C4—C5—C7i | 121.9 (4) | C16—C17—H10 | 118.0 |
C6—C5—C7i | 119.0 (3) | N2—C18—C19 | 122.9 (4) |
C5—C6—C7 | 122.5 (3) | N2—C18—H11 | 118.5 |
C5—C6—C12 | 118.5 (3) | C19—C18—H11 | 118.6 |
C7—C6—C12 | 119.0 (3) | C15—C19—C18 | 120.0 (4) |
C5i—C7—C6 | 118.5 (3) | C15—C19—H12 | 120.0 |
C5i—C7—C8 | 122.6 (4) | C18—C19—H12 | 120.0 |
C6—C7—C8 | 118.9 (4) | O3—C20—C21 | 122.9 (4) |
C7—C8—C9 | 122.0 (4) | O3—C20—C25 | 117.0 (4) |
C7—C8—H3 | 119.0 | C21—C20—C25 | 120.1 (4) |
C9—C8—H3 | 119.0 | C20—C21—C22 | 120.0 (4) |
C8—C9—C10 | 119.9 (4) | C20—C21—H13 | 120.0 |
C8—C9—H4 | 120.1 | C22—C21—H13 | 120.0 |
C10—C9—H4 | 120.0 | C21—C22—C23 | 120.5 (4) |
C9—C10—C11 | 118.8 (4) | C21—C22—H14 | 119.7 |
C9—C10—C12 | 121.1 (4) | C23—C22—H14 | 119.7 |
C11—C10—C12 | 120.1 (3) | C22—C23—C24 | 118.9 (4) |
O1—C11—N1 | 120.6 (4) | C22—C23—H15 | 120.5 |
O1—C11—C10 | 122.9 (4) | C24—C23—H15 | 120.6 |
N1—C11—C10 | 116.5 (3) | C23—C24—C25 | 120.9 (4) |
C2—C12—C6 | 119.9 (4) | C23—C24—H16 | 119.6 |
C2—C12—C10 | 121.0 (4) | C25—C24—H16 | 119.6 |
C6—C12—C10 | 119.1 (3) | C20—C25—C24 | 119.6 (4) |
N1—C13—C14 | 111.0 (3) | C20—C25—H17 | 120.2 |
N1—C13—H5 | 109.1 | C24—C25—H17 | 120.2 |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H18···N2 | 1.08 (4) | 1.65 (4) | 2.717 (4) | 170 (3) |
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